@article {253, title = {Diastereoselective, photocatalytic [2~+~2] dimerizations of alkenylboronic acids promoted by sugar alcohols}, journal = {Tetrahedron Lett.}, volume = {171-172}, year = {2025}, month = {2025/11/15/}, pages = {155827}, abstract = {In the presence of the sugar alcohol meso-erythritol, trans-2-arylvinylboronic acids undergo regio- and diastereoselective, photocatalytic [2~+~2] cycloadditions, generating all-trans-substituted cyclobutane-1,2-bis(boronic acid) derivatives. A covalent templating mechanism is proposed, involving in situ formation of a 2:1 boronic acid:tetraol adduct {\textendash} likely a mixed boronic ester/hemiboronic ester. The protocol has been applied to various substituted trans-2-arylvinylboronic acid derivatives, providing access to chiral, C2-symmetric cyclobutane derivatives that would be challenging to synthesize by other means.}, keywords = {Boronic acids, Cyclobutanes., Photocatalysis., [2~+~2] cycloaddition}, isbn = {0040-4039}, url = {https://www.sciencedirect.com/science/article/pii/S0040403925003764}, author = {Charlery, Anastasia and Desai, Shrey P. and Zambri, Matthew T. and Taylor, Mark S.} } @article {250, title = {Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles}, journal = {The Journal of Organic Chemistry}, volume = {90}, year = {2025}, month = {2025/05/09}, pages = {6278 - 6293}, isbn = {0022-3263}, url = {https://doi.org/10.1021/acs.joc.5c00380}, author = {Zheng, Benjamin and Taylor, Mark S.} } @article {247, title = {Site-Selective O-Arylation of Carbohydrate Derivatives through Nickel{\textendash}Photoredox Catalysis}, journal = {The Journal of Organic Chemistry}, volume = {90}, year = {2025}, month = {2025/01/10}, pages = {479 - 492}, isbn = {0022-3263}, url = {https://doi.org/10.1021/acs.joc.4c02402}, author = {Jdanova, Sofia and Guthrie, James G. and Taylor, Mark S.} } @article {237, title = {Boronic Acid-Catalyzed Regio- and Stereoselective N-Glycosylations of Purines and Other Azole Heterocycles: Access to Nucleoside Analogues}, journal = {Journal of the American Chemical Society}, volume = {146}, year = {2024}, month = {2024/02/21}, pages = {4973 - 4984}, isbn = {0002-7863}, url = {https://doi.org/10.1021/jacs.3c14434}, author = {Desai, Shrey P. and Yatzoglou, Giorgos and Turner, Julia A. and Taylor, Mark S.} } @article {240, title = {On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals}, journal = {Organic \& Biomolecular Chemistry}, volume = {22}, year = {2024}, month = {2024}, pages = {3225{\textendash}3229}, abstract = {A computational study of the mechanism of hydrogen atom transfer-induced carboxylate elimination from monoacylated 1,2-diol groups in pyranosides is presented. A comprehensive analysis of the 1,2-migration, elimination and fragmentation pathways reveals that concerted elimination via a 7-membered, hydrogen-bonded transition state is favored. Relative rates of elimination inferred from an intramolecular competition experiment are consistent with the trends obtained from the calculations.}, isbn = {1477-0520}, url = {http://dx.doi.org/10.1039/D4OB00241E}, author = {Turner, Julia A. and Zipse, Hendrik and Taylor, Mark S.} } @article {246, title = {Rhodium-Catalyzed Enantioselective Ring-Openings of Oxabicyclic Alkenes with Azole Nucleophiles}, journal = {The Journal of Organic Chemistry}, volume = {89}, year = {2024}, month = {2024/11/15}, pages = {16889 - 16898}, isbn = {0022-3263}, url = {https://doi.org/10.1021/acs.joc.4c02437}, author = {Zambri, Matthew T. and Grewal, Armaan and Lautens, Mark and Taylor, Mark S.} } @article {239, title = {Synergistic Organoboron/Palladium Cocatalyzed Dehydrative Couplings of Azoles with Allylic Alcohols: A Combined Experimental and Computational Mechanistic Investigation}, journal = {ACS Catalysis}, year = {2024}, month = {2024/04/16}, pages = {6728 - 6739}, url = {https://doi.org/10.1021/acscatal.4c01010}, author = {Zambri, Matthew T. and Hou, Teh Ren and Jdanova, Sofia and Taylor, Mark S.} } @article {235, title = {Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry}, journal = {Chemical Science}, volume = {15}, year = {2024}, month = {2024}, pages = {1204 - 1236}, abstract = {This review article highlights the diverse ways in which recent developments in the areas of photocatalysis and visible light photochemistry are impacting synthetic carbohydrate chemistry. The major topics covered are photocatalytic glycosylations, generation of radicals at the anomeric position, transformations involving radical formation at non-anomeric positions, additions to glycals, processes initiated by photocatalytic hydrogen atom transfer from sugars, and functional group interconversions at OH and SH groups. Factors influencing stereo- and site-selectivity in these processes, along with mechanistic aspects, are discussed.}, isbn = {2041-6520}, url = {http://dx.doi.org/10.1039/D3SC05400D}, author = {Gorelik, Daniel J. and Desai, Shrey P. and Jdanova, Sofia and Turner, Julia A. and Taylor, Mark S.} } @article {206, title = {Mechanistic Study of the Copper(II)-Mediated Site-Selective O-Arylation of Glycosides with Arylboronic Acids}, journal = {The Journal of Organic Chemistry}, volume = {88}, year = {2023}, month = {2023/03/17}, pages = {3487 - 3498}, isbn = {0022-3263}, url = {https://doi.org/10.1021/acs.joc.2c02693}, author = {Jdanova, Sofia and Taylor, Mark S.} } @article {229, title = {Organoboron / Palladium Cocatalytic Allylation of N-H-Sulfoximines Using Allylic Alcohols}, journal = {Organic Letters}, volume = {In press}, year = {2023}, month = {2023/11/14}, isbn = {1523-7060}, doi = {https://doi.org/10.1021/acs.orglett.3c03323}, author = {Zambri, Matthew T. and Ho, Celine and Taylor, Mark S.} } @article {233, title = {Synergistic Organoboron/Palladium Catalysis for Regioselective N-Allylation of 2-Pyridones, 4-Pyridones, and Related Ambident Heterocycles}, journal = {Synlett}, year = {2023}, month = {2023/11/15}, abstract = {The use of a boronic acid co-catalyst along with a palladium complex enables efficient dehydrative couplings of allylic alcohols and tautomerizable heterocycles. The protocol has been applied to achieve N-allylations of 2-pyridones, 4-pyridones, 4-pyrimidinones, and their benzo-fused derivatives.}, keywords = {Allylation, Boronic acids, heterocycles, palladium, regioselectivity}, isbn = {0936-52141437-2096}, url = {http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0043-1763618}, author = {Yatzoglou, Giorgos and Zambri, Matthew T. and Desai, Shrey P. and Taylor, Mark S.} } @article {205, title = {Synthesis of 1,2,4,5-oxadiazaboroles by three-component condensations of hydroxylamines, nitriles, and diarylborinic acids}, journal = {Canadian Journal of Chemistry}, year = {2023}, month = {2023/02/23}, abstract = {A method for the synthesis of substituted 1,2,4,5-oxadiazaboroles is described, in which hydroxylamines, nitriles, and diarylborinic acids engage in a three-component condensation reaction. The protocol provides access to a substitution pattern that is not readily available through other methods?namely, 2,3-disubstitution, with a tetracoordinate boron center. Structures of representative members of this class of heterocycles were determined by single crystal X-ray diffraction analysis.A method for the synthesis of substituted 1,2,4,5-oxadiazaboroles is described, in which hydroxylamines, nitriles, and diarylborinic acids engage in a three-component condensation reaction. The protocol provides access to a substitution pattern that is not readily available through other methods?namely, 2,3-disubstitution, with a tetracoordinate boron center. Structures of representative members of this class of heterocycles were determined by single crystal X-ray diffraction analysis.}, isbn = {0008-4042}, url = {https://doi.org/10.1139/cjc-2022-0200}, author = {Ge, Zhenlu and Lough, Alan J. and Taylor, Mark S.} } @article {230, title = {Understanding the Origins of Site Selectivity in Hydrogen Atom Transfer Reactions from Carbohydrates to the Quinuclidinium Radical Cation: A Computational Study}, journal = {The Journal of Organic Chemistry}, volume = {88}, year = {2023}, month = {2023/05/05}, pages = {5713 - 5730}, isbn = {0022-3263}, url = {https://doi.org/10.1021/acs.joc.3c00181}, author = {Turner, Julia A. and Adrianov, Timur and Taylor, Mark S.} } @article {192, title = {Borinic Acid Catalyzed Regioselective N-Alkylation of Azoles}, journal = {The Journal of Organic Chemistry}, volume = {87}, year = {2022}, month = {2022/04/15}, pages = {5385 - 5394}, isbn = {0022-3263}, url = {https://doi.org/10.1021/acs.joc.2c00281}, author = {Desai, Shrey P. and Zambri, Matthew T. and Taylor, Mark S.} } @article {193, title = {Catalyst-Controlled, Site-Selective Sulfamoylation of Carbohydrate Derivatives}, journal = {Organic Letters}, volume = {24}, year = {2022}, month = {2022/07/29}, pages = {5249 - 5253}, isbn = {1523-7060}, url = {https://doi.org/10.1021/acs.orglett.2c01590}, author = {Gorelik, Daniel J. and Turner, Julia A. and Taylor, Mark S.} } @article {191, title = {Effects of Configuration and Substitution on C{\textendash}H Bond Dissociation Enthalpies in Carbohydrate Derivatives: A Systematic Computational Study}, journal = {The Journal of Organic Chemistry}, volume = {87}, year = {2022}, month = {2022/01/21}, pages = {1421 - 1433}, isbn = {0022-3263}, url = {https://doi.org/10.1021/acs.joc.1c02725}, author = {Turner, Julia A. and Adrianov, Timur and Zakaria, Mia Ahed and Taylor, Mark S.} } @article {194, title = {Synergistic Organoboron/Palladium Catalysis for Regioselective N-Allylations of Azoles with Allylic Alcohols}, journal = {Organic Letters}, volume = {24}, year = {2022}, month = {2022/10/21}, pages = {7617 - 7621}, isbn = {1523-7060}, url = {https://doi.org/10.1021/acs.orglett.2c03084}, author = {Zambri, Matthew T. and Hou, Teh Ren and Taylor, Mark S.} } @article {186, title = {Diarylborinic Acid-Catalyzed Regioselective Ring Openings of Epoxy Alcohols with Pyrazoles, Imidazoles, Triazoles, and Other Nitrogen Heterocycles}, journal = {Organic Letters}, volume = {23}, year = {2021}, month = {2021/08/30}, pages = {7049{\textendash}7054}, isbn = {1523-7060}, url = {https://doi.org/10.1021/acs.orglett.1c02412}, author = {Desai, Shrey P. and Taylor, Mark S.} } @article {175, title = {Neutral Chiral Tetrakis-Iodo-Triazole Halogen-Bond Donor for Chiral Recognition and Enantioselective Catalysis}, journal = {Chemistry {\textendash} A European Journal}, volume = {27}, year = {2021}, month = {2020/11/19}, pages = {2315{\textendash}2320}, abstract = {

Halogen bonding represents a powerful tool in the field of noncovalent interactions. However, applications in enantioselective recognition and catalysis remain almost nonexistent, due in part to the distinct features of halogen bonds, including long covalent and noncovalent bond distances and high directionality. Herein, we present a novel chiral tetrakis-iodo-triazole structure as a neutral halogen bond donor for both chiral anion-recognition and enantioinduction in ion-pair organocatalysis. NMR-titration studies revealed significant differences in anion affinity between the halogen bonding receptor and its hydrogen bonding parent. Selective recognition of chiral dicarboxylates and asymmetric induction in a benchmark organocatalytic reaction were demonstrated using the halogen bond donor. Inversions in the absolute sense of chiral recognition, enantioselectivity, and chiroptical properties relative to the related hydrogen donor were observed. Computational modeling suggested that these effects were the result of distinct anion-binding modes for the halogen- versus hydrogen-bond donors.

}, keywords = {Chiral anion recognition, DFT, Halogen bonding, NMR-titration, organocatalysis}, isbn = {0947-6539}, url = {https://doi.org/10.1002/chem.202005016}, author = {Ostler, Florian and Piekarski, Dariusz G. and Danelzik, Tobias and Taylor, Mark and Garc{\'\i}a Manche{\~n}o, Olga} } @article {190, title = {Photocatalytic, site-selective oxidations of carbohydrates}, journal = {Chemical Communications}, volume = {57}, year = {2021}, month = {2021}, pages = {12135 - 12138}, abstract = {Site-selective oxidations of carbohydrates, employing acridinium photocatalysis and quinuclidine hydrogen atom transfer catalysis, are presented. Protocols have been developed for oxidations of all-equatorial carbohydrates as well as those containing cis-1,2-diols. Site-selectivity reflects the relative rates of hydrogen atom transfer from the carbohydrate C{\textendash}H bonds, and can be enhanced using a phosphate hydrogen-bonding or boronic acid catalyst.}, isbn = {1359-7345}, doi = {http://dx.doi.org/10.1039/D1CC05124E}, url = {https://hdl.handle.net/1807/144665}, author = {Gorelik, Daniel J. and Dimakos, Victoria and Adrianov, Timur and Taylor, Mark S.} } @article {180, title = {Recent advances in the direct O-arylation of carbohydrates}, journal = {Organic \& Biomolecular Chemistry}, volume = {19}, year = {2021}, month = {2021}, pages = {514{\textendash}524}, abstract = {

Methods for the O-arylation of hydroxyl and hemiacetal groups in carbohydrates via C(sp2){\textendash}O bond formation are discussed. Such methods provide an alternative disconnection to the traditional approach of nucleophilic substitution between a sugar-derived electrophile and a phenol or phenoxide nucleophile. They have led to new opportunities for stereoselectivity, site-selectivity and chemoselectivity in the preparation of O-aryl glycosides and carbohydrate-derived aryl ethers, compounds that are useful for a broad range of applications in medicinal chemistry, glycobiology and organic synthesis.

}, isbn = {1477-0520}, url = {http://dx.doi.org/10.1039/D0OB02009E}, author = {Dimakos, Victoria and Taylor, Mark S.} } @article {184, title = {Site- and Stereoselective C{\textendash}H Alkylations of Carbohydrates Enabled by Cooperative Photoredox, Hydrogen Atom Transfer, and Organotin Catalysis}, journal = {Organic Letters}, volume = {23}, year = {2021}, month = {2021/07/02}, pages = {5180 - 5185}, isbn = {1523-7060}, url = {https://doi.org/10.1021/acs.orglett.1c01718}, author = {Gorelik, Daniel J. and Turner, Julia A. and Virk, Tarunpreet S. and Foucher, Daniel A. and Taylor, Mark S.} } @article {185, title = {Synthesis of Ketodeoxysugars from Acylated Pyranosides Using Photoredox Catalysis and Hydrogen Atom Transfer}, journal = {ACS Catalysis}, volume = {11}, year = {2021}, month = {2021/09/03}, pages = {11171 - 11179}, url = {https://doi.org/10.1021/acscatal.1c03050}, author = {Turner, Julia A. and Rosano, Nicholas and Gorelik, Daniel J. and Taylor, Mark S.} } @article {168, title = {Anion recognition based on halogen, chalcogen, pnictogen and tetrel bonding}, journal = {Coordination Chemistry Reviews}, volume = {413}, year = {2020}, month = {2020/06/15/}, pages = {213270}, abstract = {

Compounds incorporating Group 14{\textendash}17 elements as electron-deficient sites are capable of attractive, directional interactions with Lewis bases. These noncovalent interactions are known as tetrel, pnictogen, chalcogen and halogen bonding, respectively. When the Lewis base is a negatively charged species, such interactions can be employed as the basis for the development of anion receptors, which are of interest from a fundamental standpoint and in applications ranging from chemical sensing to catalysis and medicinal chemistry. Halogen bonding and related interactions offer intriguing features in this context, including distinctive patterns of anion selectivity and solvent effects, along with unique opportunities for structural variation and synthetic access. This review article summarizes advances in anion recognition using halogen, chalcogen, pnictogen and tetrel bonding, with a focus on examples for which solution-phase thermodynamic data have been obtained.

}, keywords = {Anion recognition, Chalcogen bonding, Halogen bonding, noncovalent interactions, Pnictogen bonding, supramolecular chemistry, Tetrel bonding}, isbn = {0010-8545}, url = {http://www.sciencedirect.com/science/article/pii/S0010854519307805}, author = {Taylor, Mark S.} } @article {167, title = {Borinic Acid-Catalyzed Regioselective Ring-Opening of 3,4- and 2,3-Epoxy Alcohols with Halides}, journal = {Advanced Synthesis \& Catalysis}, volume = {362}, year = {2020}, month = {2020/01/23}, pages = {398 - 403}, abstract = {

Abstract Methods for the regioselective ring-opening of 3,4-epoxy alcohols and 2,3-epoxy alcohols with halide nucleophiles, using a diarylborinic acid catalyst, are disclosed. Ring-opening occurs at the position proximal to the OH group, an effect ascribed to a catalytic tethering mechanism whereby coordination to the substrate OH group positions the diarylborinic acid to deliver a coordinated halide nucleophile. These methods provide access to halohydrin substitution patterns that were not previously accessible through catalytic epoxide ring-opening reactions.

}, keywords = {boron, halides, homogeneous catalysis, regioselectivity.}, isbn = {1615-4150}, url = {https://doi.org/10.1002/adsc.201901268}, author = {Wang, Grace and Taylor, Mark S.} } @article {181, title = {Site-Selective, Organoboron-Catalyzed Polymerization of Pyranosides: Access to Sugar-Derived Polyesters with Tunable Properties}, journal = {Macromolecules}, volume = {53}, year = {2020}, month = {2020/10/13}, pages = {8192{\textendash}8201}, isbn = {0024-9297}, url = {https://doi.org/10.1021/acs.macromol.0c01686}, author = {Slavko, Ekaterina and Taylor, Mark S.} } @article {166, title = {Site-selective redox isomerizations of furanosides using a combined arylboronic acid/photoredox catalyst system}, journal = {Chemical Science}, volume = {11}, year = {2020}, month = {2020}, pages = {1531 - 1537}, abstract = {

In the presence of an arylboronic acid and a hydrogen atom transfer mediator under photoredox conditions, furanoside derivatives undergo site-selective redox isomerizations to 2-keto-3-deoxyfuranosides. Experimental evidence and computational modeling suggest that the transformation takes place by abstraction of the hydrogen atom from the 2-position of the furanoside-derived arylboronic ester, followed by C3{\textendash}O bond cleavage via spin-center shift. This mechanism is reminiscent of the currently accepted pathway for the formation of 3'-ketodeoxynucleotides by ribonucleotide reductase enzymes.

}, isbn = {2041-6520}, url = {http://dx.doi.org/10.1039/C9SC05173B}, author = {Dimakos, Victoria and Gorelik, Daniel and Su, Hsin Y. and Garrett, Graham E. and Hughes, Gregory and Shibayama, Hiromitsu and Taylor, Mark S.} } @article {163, title = {Boronic acid-promoted site-selective Fischer esterifications of sugar alcohols}, journal = {Green Chemistry}, volume = {21}, year = {2019}, month = {2019}, pages = { 5363{\textendash}5367 }, isbn = {1463-9262}, url = {http://dx.doi.org/10.1039/C9GC00901A}, author = {Manhas, Sanjay and Lin, Yu Chen and Wang, Grace and Kyne, Luke T. and Taylor, Mark S.} } @article {155, title = {Chiral phosphine ligand libraries based on the Bull{\textendash}James three-component supramolecular assembly}, journal = {Supramolecular Chemistry}, volume = {31}, year = {2019}, month = {2019/01/06}, pages = {190{\textendash}202}, isbn = {1061-0278}, doi = {https://doi.org/10.1080/10610278.2018.1564829}, url = {https://doi.org/10.1080/10610278.2018.1564829}, author = {Su, Hsin Y. and Gorelik, Daniel and Taylor, Mark S.} } @article {165, title = {Copper-mediated anomeric O-arylation with organoboron reagents}, journal = {Organic \& Biomolecular Chemistry}, volume = {17}, year = {2019}, month = {2019}, pages = {5671 - 5674}, abstract = {

Copper-mediated couplings of arylboroxines with glycosyl hemiacetals furnish O-aryl glycosides via Csp2{\textendash}O bond formation. The method enables the anomeric O-arylation of protected pyranose and furanose derivatives, and is tolerant of functionalized arylboroxine partners. Whereas mixtures of anomers are formed from glucopyranose, galactopyranose and arabinofuranose hemiacetals, the α-anomer is generated selectively from mannopyranose and mannofuranose-derived substrates.

}, isbn = {1477-0520}, url = {http://dx.doi.org/10.1039/C9OB01022J}, author = {Dimakos, Victoria and Liu, Jacklyn J. W. and Ge, Zhenlu and Taylor, Mark S.} } @article {154, title = {Diarylborinic Acid-Catalyzed, Site-Selective Sulfation of Carbohydrate Derivatives}, journal = {The Journal of Organic Chemistry}, volume = {84}, year = {2019}, month = {2019/01/08}, pages = {900{\textendash}908}, isbn = {0022-3263}, doi = {https://doi.org/10.1021/acs.joc.8b02792}, url = {https://doi.org/10.1021/acs.joc.8b02792}, author = {Gorelik, Daniel and Lin, Yu Chen and Briceno-Strocchia, Alvaro I. and Taylor, Mark S.} } @article {169, title = {Rhodium-Catalyzed Tandem Isomerization{\textendash}Allylation: From Diallyl Carbonates to α-Quaternary Aldehydes}, journal = {ACS Catalysis}, volume = {9}, year = {2019}, month = {2019/12/06}, pages = {11808 - 11812}, url = {https://doi.org/10.1021/acscatal.9b04128}, author = {Masson-Makdissi, Jeanne and Jang, Young Jin and Prieto, Liher and Taylor, Mark S. and Lautens, Mark} } @article {158, title = {Site-Selective and Stereoselective C{\textendash}H Alkylations of Carbohydrates via Combined Diarylborinic Acid and Photoredox Catalysis}, journal = {Journal of the American Chemical Society}, volume = {141}, year = {2019}, month = {2019/03/22}, pages = {5149{\textendash}5153}, isbn = {0002-7863}, url = {https://doi.org/10.1021/jacs.9b01531}, author = {Dimakos, Victoria and Su, Hsin Y. and Garrett, Graham E. and Taylor, Mark S.} } @article {145, title = {Borinic Acid / Halide Co-catalyzed Semipinacol Rearrangements of 2,3-Epoxy Alcohols}, journal = {Organic Letters}, volume = {20}, year = {2018}, month = {2018/08/15}, pages = {5327{\textendash}{\textendash}5331}, isbn = {1523-7060}, url = {https://doi.org/10.1021/acs.orglett.8b02248}, author = {Tanveer, Kashif and Kim, Seung-Joon and Taylor, Mark S.} } @article {146, title = {Borinic Acid-Catalyzed, Regioselective Ring Opening of 3,4-Epoxy Alcohols}, journal = {Organic Letters}, volume = {20}, year = {2018}, month = {2018/08/27}, pages = {5375{\textendash}5379}, isbn = {1523-7060}, url = {https://doi.org/10.1021/acs.orglett.8b02295}, author = {Wang, Grace and Garrett, Graham E. and Taylor, Mark S.} } @article {147, title = {Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester}, journal = {Carbohydrate Research}, volume = {470}, year = {2018}, month = {2018/12/01/}, pages = {42 - 49}, abstract = {

An N-methylpyridinium-4-boronic ester acts as a catalyst for dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals. The catalytic protocol is tolerant of functionalized acceptors, including alcohols bearing isopropylidene ketal, tert-butyl carbamate or benzyl carbamate groups. The results demonstrate that organoboron-catalyzed substitution reactions of alcohols, which have previously been conducted on π-activated (benzylic, allylic or propargylic) substrates, can also be used to achieve C{\textendash}O bond formation from carbohydrate-derived hemiacetals.

}, keywords = {2-Deoxyglycoside, Boronic acid, Catalysis, Glycosidation}, isbn = {0008-6215}, url = {http://www.sciencedirect.com/science/article/pii/S0008621518304579}, author = {Manhas, Sanjay and Taylor, Mark S.} } @article {148, title = {Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives}, journal = {Chemical Reviews}, volume = {118}, year = {2018}, month = {11/2018}, pages = {11457{\textendash}11517}, type = {Thematic Review}, doi = {10.1021/acs.chemrev.8b00442}, author = {Dimakos, Victoria and Taylor, Mark S.} } @article {132, title = {Borinic acid-catalyzed stereo- and site-selective synthesis of beta-glycosylceramides}, journal = {Chemical Communications}, volume = {53}, year = {2017}, month = {2017}, pages = {5978 - 5980}, abstract = {

A method for activation of unprotected ceramides towards stereo- and site-selective glycosylation is described. Two-point binding of a diarylborinic acid catalyst to the ceramide accelerates its reactions with {\textquoteright}armed{\textquoteright} glycosyl methanesulfonate donors, resulting in the formation of a [small beta]-glycosidic linkage at the primary OH group.

}, isbn = {1359-7345}, url = {http://dx.doi.org/10.1039/C7CC01673E}, author = {D{\textquoteright}Angelo, Kyan A. and Taylor, Mark S.} } @article {139, title = {Boronic acids as phase-transfer reagents for Fischer glycosidations in low-polarity solvents}, journal = {The Journal of Organic Chemistry}, volume = {82}, year = {2017}, month = {10/2017}, pages = {11406{\textendash}11417}, type = {Article}, doi = {http://dx.doi.org/10.1021/acs.joc.7b01880}, author = {Manhas, Sanjay and Taylor, Mark S.*} } @article {87, title = {Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates}, journal = {Organic \& Biomolecular Chemistry}, volume = {15}, year = {2017}, month = {2017}, pages = {132 - 143}, abstract = {

Procedures for selective installation of acyl, silyl ether and para-methoxybenzyl (PMB) ether groups to glycoside substrates have been developed, employing phenylboronic esters as protected intermediates. The sequence of boronic ester formation, functionalization and deprotection can be accomplished with only a single purification step, and the boronic acid component can be recovered and reused after deprotection. Key advances include the identification of reaction conditions for installation of PMB groups in the presence of boronic esters, and the use of the {\textquoteright}phase switching{\textquoteright} protocol developed by Hall and co-workers as an efficient method for boronic ester cleavage. The relatively mild conditions for boronate deprotection are tolerant of several functional groups, including esters, silyl ethers, ketals and thioglycosides.

}, isbn = {1477-0520}, url = {http://dx.doi.org/10.1039/C6OB02278B}, author = {Mancini, Ross S. and Lee, Jessica B. and Taylor, Mark S.} } @article {138, title = {Catalyst-controlled polycondensation of glycerol with diacyl chlorides: linear polyesters from a trifunctional monomer}, journal = {Chemical Science}, volume = {8}, year = {2017}, month = {2017}, pages = {7106{\textendash}7111}, abstract = {

Diarylborinic acids catalyze the formation of linear polyesters from glycerol, a trifunctional, carbohydrate-based monomer. The selective activation of 1,2-diols over isolated alcohols by the organoboron catalyst results in polymers that are essentially free of branching or cross-linking and possess a high fraction of 1,3-enchained glycerol units, as assessed by 1H and 13C NMR spectroscopy. The ability to generate well-defined polyester architectures from glycerol is significant in light of the numerous applications of such macromolecules, particularly in the biomedical area. Isomerization, post-polymerization functionalization and controlled cross-linking reactions of the obtained linear poly(glycerol esters) are demonstrated.

}, isbn = {2041-6520}, url = {http://dx.doi.org/10.1039/C7SC01886J}, author = {Slavko, Ekaterina and Taylor, Mark S.} } @article {135, title = {Exploring the construction of multicompartmental micelles by halogen bonding of complementary macromolecules}, journal = {Faraday Discussions}, volume = {203}, year = {2017}, month = {2017}, pages = {285{\textendash}299}, abstract = {

An approach to the construction of multicompartmental micelles, using halogen bonding between complementary macromolecules, is described. The design involves a sequential assembly protocol, in which the initial compartments are formed by interpolymer halogen bonding, followed by the collapse of a second, hydrophobic compartment upon transfer to aqueous solvent. Triblock terpolymers incorporating a halogen bond accepting segment have been synthesized. Transmission electron microscopy was used to characterize multicompartmental assemblies generated from these terpolymers in the presence of a halogen bond donor-functionalized polystyrene derivative.

}, isbn = {1359-6640}, url = {http://dx.doi.org/10.1039/C7FD00111H}, author = {Vanderkooy, Alan and Taylor, Mark S.} } @article {68, title = {Mechanism of an Organoboron-Catalyzed Domino Reaction: Kinetic and Computational Studies of Borinic Acid-Catalyzed Regioselective Chloroacylation of 2,3-Epoxy Alcohols}, journal = {The Journal of Organic Chemistry}, volume = {82}, year = {2017}, month = {2017/01/20}, pages = {1085 - 1095}, isbn = {0022-3263}, doi = {http://dx.doi.org/10.1021/acs.joc.6b02702}, url = {http://pubs.acs.org/articlesonrequest/AOR-IieqdIq58YdPtPbNBpMe}, author = {Garrett, Graham E. and Tanveer, Kashif and Taylor, Mark S.} } @article {127, title = {A Nonlinear Ordinary Differential Equation for Generating Graphical Rate Equations from Concentration Versus Time Data}, journal = {Topics in Catalysis}, volume = {60}, year = {2017}, month = {04/2017}, pages = {554{\textendash}563}, chapter = {554}, abstract = {

When reaction progress kinetic analysis is implemented on data obtained using a spectroscopic or chromatographic technique such as ATR{\textendash}FTIR, NMR, absorbance spectroscopy, HPLC or GC, an initial step involves fitting a mathematical function to the experimental concentration versus time data. This function is then differentiated to give graphs of rate versus substrate concentration (graphical rate equations). It is important that the function be able to accurately describe the experimental data without introducing bias or artifacts. Here, we put forward a nonlinear ordinary differential equation that can be fitted to experimental concentration versus time data for applications in reaction progress kinetic analysis. We show that it can be applied to data from catalytic transformations showing diverse types of kinetic behavior.

}, isbn = {1572-9028}, url = {http://dx.doi.org/10.1007/s11244-017-0739-7}, author = {Garrett, Graham E. and Taylor, Mark S.} } @article {128, title = {P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis}, journal = {The Journal of Organic Chemistry}, volume = {82}, year = {2017}, month = {2017/03/17}, pages = {3173 - 3182}, isbn = {0022-3263}, doi = {http://dx.doi.org/10.1021/acs.joc.7b00199}, url = {http://pubs.acs.org/articlesonrequest/AOR-RxbAquas9MyXGG3VsVVV}, author = {Su, Hsin Y. and Taylor, Mark S.} } @article {93, title = {Reversible covalent interactions of beta-aminoboronic acids with carbohydrate derivatives}, journal = {Chemical Communications}, volume = {53}, year = {2017}, month = {2017}, pages = {1809 - 1812}, abstract = {

[small beta]-Aminoalkylboronic acids are capable of binding to carbohydrate derivatives through reversible covalent interactions. An anthracene-bearing [small beta]-aminoboronic acid has been synthesized, enabling determinations of association constants for binding of sugars by fluorescence spectroscopy. The diol-binding properties of [small beta]-aminoboronic acids are also useful in catalysis: one such compound displays remarkably high activity for regioselective O-acylation of a pyranoside derivative.

}, isbn = {1359-7345}, url = {http://dx.doi.org/10.1039/C6CC09640A}, author = {Garrett, Graham E. and Diaz, Diego B. and Yudin, Andrei K. and Taylor, Mark S.} } @article {130, title = {Self-Assembly of Polymer Nanostructures through Halogen Bonding Interactions of an Iodoperfluoroarene-Functionalized Polystyrene Derivative}, journal = {Macromolecules}, volume = {50}, year = {2017}, month = {2017/05/12}, pages = {3807{\textendash}3818}, chapter = {3807}, isbn = {0024-9297}, doi = {http://pubs.acs.org/doi/abs/10.1021/acs.macromol.7b00281}, url = {http://pubs.acs.org/articlesonrequest/AOR-nFeBQIibm6ZBY62zVkdp}, author = {Vanderkooy, Alan and Pfefferkorn, Philipp and Taylor, Mark S.} } @article {137, title = {Sequential Functionalizations of Carbohydrates Enabled by Boronic Esters as Switchable Protective/Activating Groups}, journal = {The Journal of Organic Chemistry}, volume = {82}, year = {2017}, month = {2017/08/17}, pages = {8777{\textendash}8791}, isbn = {0022-3263}, doi = {http://dx.doi.org/10.1021/acs.joc.7b01605}, url = {http://pubs.acs.org/articlesonrequest/AOR-YU36CZbTpvKNhdumyRJP}, author = {Mancini, Ross S. and Lee, Jessica B. and Taylor, Mark S.} } @article {140, title = {Site-selective, copper-mediated O-arylation of carbohydrate derivatives}, journal = {Journal of the American Chemical Society}, volume = {139}, year = {2017}, month = {10/2017}, pages = {15515{\textendash}15521}, doi = {http://dx.doi.org/10.1021/jacs.7b09420}, author = {Dimakos, V. and Garrett, G. E. and Taylor, Mark S.*} } @article {92, title = {Anion recognition by a bidentate chalcogen bond donor}, journal = {Chemical Communications}, volume = {52}, year = {2016}, month = {2016}, pages = {9881 - 9884}, abstract = {

Perfluoroaryl-substituted tellurophenes act as anion receptors through noncovalent chalcogen bonding interactions. Linking two tellurophenes through an ethynylene group results in a significant level of chelate cooperativity, thus demonstrating that chalcogen bonding can be used to achieve multidentate anion recognition.

}, isbn = {1359-7345}, url = {http://dx.doi.org/10.1039/C6CC04818H}, author = {Garrett, Graham E. and Carrera, Elisa I. and Seferos, Dwight S. and Taylor, Mark S.} } @article {69, title = {Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates}, journal = {Journal of the American Chemical Society}, volume = {138}, year = {2016}, month = {2016/08/31}, pages = {11058 - 11066}, isbn = {0002-7863}, doi = {http://dx.doi.org/10.1021/jacs.6b06943}, url = {http://pubsdc3.acs.org/articlesonrequest/AOR-5T8XQJ8IReZtTNKBxQev}, author = {D{\textquoteright}Angelo, Kyan A. and Taylor, Mark S.} } @article {88, title = {Boronic acid/Bronsted acid co-catalyst systems for the synthesis of 2H-chromenes from phenols and alpha,beta-unsaturated carbonyls}, journal = {Organic \& Biomolecular Chemistry}, volume = {14}, year = {2016}, month = {2016}, pages = {6703 - 6711}, abstract = {

Protocols for the synthesis of substituted 2H-chromenes from [small alpha],[small beta]-unsaturated carbonyls and phenols are described. Optimal combinations of arylboronic acids and Bronsted acids have been identified, such that both can be employed in catalytic quantities to accelerate these condensations. The method has been used to synthesize a variety of substituted 2H-chromenes, as well as photochromic naphthopyrans. The use of pentafluorophenylboronic acid and diphenylphosphinic acid enabled an expansion of the electrophile scope to include [small alpha],[small beta]-unsaturated ketones. Hall{\textquoteright}s {\textquoteright}phase-switching{\textquoteright} of boronic acids has been exploited to achieve the separation of the two co-catalysts from unpurified reaction mixtures by a simple liquid-liquid extraction.

}, isbn = {1477-0520}, url = {http://dx.doi.org/10.1039/C6OB01026A}, author = {Dimakos, Victoria and Singh, Tishaan and Taylor, Mark S.} } @inbook {99, title = {Catalyst-Controlled, Regioselective Reactions of Carbohydrate Derivatives}, booktitle = {Site-Selective Catalysis}, year = {2016}, pages = {125 - 155}, publisher = {Springer International Publishing}, organization = {Springer International Publishing}, address = {Cham}, isbn = {978-3-319-26333-5}, url = {http://dx.doi.org/10.1007/128_2015_656}, author = {Taylor, Mark S.}, editor = {Kawabata, Takeo} } @inbook {112, title = {Halogen Bond-Based Receptors}, booktitle = {Reference Module in Chemistry, Molecular Sciences and Chemical Engineering}, year = {2016}, pages = { - }, publisher = {Elsevier}, organization = {Elsevier}, abstract = {

AbstractThis article presents an overview of applications of halogen bonding in host{\textendash}guest chemistry and molecular recognition. Halogen bonds are attractive interactions between covalently bonded, electron-deficient halogens and Lewis bases. In recent years, it has become increasingly evident that halogen bonding interactions of organic donors (i.e., compounds having C{\textendash}X bonds) can have appreciable strength and pronounced directionality in solution. In a relatively short period of time, impressive progress has been made in using halogen bonding as a design feature for the construction of supramolecular systems such as anion receptors and transporters, chemical sensors, molecular capsules, and mechanically interlocked molecules. Not only can halogen bonds act as {\textquotedblleft}replacements{\textquotedblright} for the hydrogen bonds that are conventionally employed in such contexts, but also they can give rise to unique properties and behaviors due to differences between the two types of interactions.

}, keywords = {Anion recognition, Halogen bonding, Mechanically interlocked molecules, Molecular encapsulation, supramolecular chemistry}, isbn = {978-0-12-409547-2}, url = {http://www.sciencedirect.com/science/article/pii/B9780124095472125272}, author = {Taylor, M.S.} } @article {89, title = {A versatile synthesis of chiral beta-aminophosphines}, journal = {Organic \& Biomolecular Chemistry}, volume = {14}, year = {2016}, month = {2016}, pages = {5665 - 5672}, abstract = {

A method for the preparation of chiral [small beta]-aminophosphines having substituted P-aryl groups is described. Ring-opening of cyclic sulfamidates with metal diarylphosphinites yields [small beta]-aminophosphine oxides, which are then reduced to the corresponding phosphines. Effects of the diarylphosphinite countercation on the regioselectivity of the ring-opening reaction (P- versus O-alkylation) are discussed. This method enables the introduction of electron-deficient, electron-rich and sterically hindered diarylphosphino groups, as demonstrated by the synthesis of a series of novel, P-aryl-substituted [small beta]-aminophosphines derived from tert-leucinol, valinol and phenylglycinol. Access to these derivatives will create new opportunities for steric and electronic tuning of [small beta]-aminophosphine-derived chiral ligands and organocatalysts.

}, isbn = {1477-0520}, url = {http://dx.doi.org/10.1039/C5OB02439K}, author = {Su, Hsin Y. and Song, Yixiong and Taylor, Mark S.} } @inbook {100, title = {Anion Recognition in Solution via Halogen Bonding}, booktitle = {Halogen Bonding II: Impact on Materials Chemistry and Life Sciences}, year = {2015}, pages = {27 - 48}, publisher = {Springer International Publishing}, organization = {Springer International Publishing}, address = {Cham}, isbn = {978-3-319-15732-0}, url = {http://dx.doi.org/10.1007/128_2014_588}, author = {Taylor, Mark S.}, editor = {Metrangolo, Pierangelo and Resnati, Giuseppe} } @article {71, title = {Borinic Acid Catalyzed, Regioselective Chloroacylations and Chlorosulfonylations of 2,3-Epoxy Alcohols}, journal = {Organic Letters}, volume = {17}, year = {2015}, month = {2015/07/17}, pages = {3482 - 3485}, isbn = {1523-7060}, url = {http://dx.doi.org/10.1021/acs.orglett.5b01541}, author = {Tanveer, Kashif and Jarrah, Kareem and Taylor, Mark S.} } @article {74, title = {Catalysis Based on Reversible Covalent Interactions of Organoboron Compounds}, journal = {Accounts of Chemical Research}, volume = {48}, year = {2015}, month = {2015/02/17}, pages = {295 - 305}, isbn = {0001-4842}, url = {http://dx.doi.org/10.1021/ar500371z}, author = {Taylor, Mark S.} } @article {73, title = {Chalcogen Bonding in Solution: Interactions of Benzotelluradiazoles with Anionic and Uncharged Lewis Bases}, journal = {Journal of the American Chemical Society}, volume = {137}, year = {2015}, month = {2015/04/01}, pages = {4126 - 4133}, isbn = {0002-7863}, url = {http://dx.doi.org/10.1021/ja512183e}, author = {Garrett, Graham E. and Gibson, Gregory L. and Straus, Rita N. and Seferos, Dwight S. and Taylor, Mark S.} } @article {70, title = {Organoboron-Promoted Regioselective Glycosylations in the Synthesis of a Saponin-Derived Pentasaccharide from Spergularia ramosa}, journal = {The Journal of Organic Chemistry}, volume = {80}, year = {2015}, month = {2015/09/04}, pages = {8501 - 8510}, isbn = {0022-3263}, doi = {http://dx.doi.org/10.1021/acs.joc.5b00950}, url = {http://pubs.acs.org/articlesonrequest/AOR-Vhw32Zbd8BvYhGkUugsw}, author = {Mancini, Ross S. and McClary, Corey A. and Anthonipillai, Stefi and Taylor, Mark S.} } @article {72, title = {Solution-Phase Self-Assembly of Complementary Halogen Bonding Polymers}, journal = {Journal of the American Chemical Society}, volume = {137}, year = {2015}, month = {2015/04/22}, pages = {5080 - 5086}, isbn = {0002-7863}, url = {http://dx.doi.org/10.1021/jacs.5b00754}, author = {Vanderkooy, Alan and Taylor, Mark S.} } @inbook {110, title = {[2-(Amino-κN)ethanolato-κO]diphenylboron}, booktitle = {Encyclopedia of Reagents for Organic Synthesis}, year = {2014}, publisher = {John Wiley \& Sons, Ltd}, organization = {John Wiley \& Sons, Ltd}, isbn = {9780470842898}, url = {http://dx.doi.org/10.1002/047084289X.rn01655}, author = {Taylor, Mark S.} } @article {103, title = {Molecular recognition: The I{\textquoteright}s have it}, journal = {Nat Chem}, volume = {6}, year = {2014}, month = {2014/12//print}, pages = {1029 - 1031}, isbn = {1755-4330}, url = {http://dx.doi.org/10.1038/nchem.2121}, author = {Taylor, Mark S.} } @article {75, title = {Organoboron-Catalyzed Regio- and Stereoselective Formation of beta-2-Deoxyglycosidic Linkages}, journal = {Organic Letters}, volume = {16}, year = {2014}, month = {2014/07/03}, pages = {3604 - 3607}, isbn = {1523-7060}, url = {http://dx.doi.org/10.1021/ol501711v}, author = {Beale, Thomas M. and Moon, Patrick J. and Taylor, Mark S.} } @article {90, title = {Synthesis of benzannulated heterocycles by twofold Suzuki-Miyaura couplings of cyclic diarylborinic acids}, journal = {Organic \& Biomolecular Chemistry}, volume = {12}, year = {2014}, month = {2014}, pages = {1391 - 1394}, abstract = {

Two-fold Suzuki-Miyaura cross-couplings of cyclic diarylborinic acids are described. This novel annulation method enables the synthesis of benzo-fused heterocycles from dihaloarenes or gem-dibromoolefins.

}, isbn = {1477-0520}, url = {http://dx.doi.org/10.1039/C3OB42065E}, author = {Dimitrijevi{\'c}, Elena and Cusimano, Madeline and Taylor, Mark S.} } @article {95, title = {9-Hetero-10-boraanthracene-derived borinic acid catalysts for regioselective activation of polyols}, journal = {Chemical Science}, volume = {4}, year = {2013}, month = {2013}, pages = {3298 - 3303}, abstract = {

Heteraborinine-derived borinic acids serve as efficient catalysts for regioselective monofunctionalization of di- and polyols. Arylborinic acids of this type, wherein the B-OH group is incorporated into a 6[small pi] electron system, display both improved catalytic activity for functionalization of diols and enhanced stability towards air oxidation relative to the {\textquoteright}parent{\textquoteright} diphenylborinic acid (Ph2BOH). These properties enable their applications at loadings as low as 0.1 mol\% and without the need for a stabilizing precatalyst ligand (e.g., ethanolamine). Complexation studies, computation and kinetic data suggest that while the heteraborinine-derived borinic acids show significantly lower association constants with substrates than Ph2BOH, this effect is more than compensated for by the increased nucleophilicity of their tetracoordinate diol adducts.

}, isbn = {2041-6520}, url = {http://dx.doi.org/10.1039/C3SC51172C}, author = {Dimitrijevi{\'c}, Elena and Taylor, Mark S.} } @article {106, title = {Applications of organoboron compounds in carbohydrate chemistry and glycobiology: analysis, separation, protection, and activation}, volume = {381}, year = {2013}, month = {2013/11/15/}, pages = {112 - 122}, abstract = {

AbstractThe reversible covalent interactions between organoboron compounds and diols have been applied for many years in carbohydrate chemistry. They form the basis of efficient methods for the detection of carbohydrates, and applications in cellular imaging and glycoprotein analysis are beginning to emerge. The interactions are also of widespread utility in carbohydrate synthesis: depending upon the coordination geometry at boron, either protection or activation of a bound diol motif may be achieved. This review article uses recent examples to illustrate the breadth of applications of organoboron compounds in carbohydrate chemistry.

}, keywords = {Boronic acids, Carbohydrates, Catalysis, Drug delivery, Fluorescence, Glycosylation}, isbn = {0008-6215}, url = {http://www.sciencedirect.com/science/article/pii/S0008621513003443}, author = {McClary, Corey A. and Taylor, Mark S.} } @article {98, title = {Halogen bonding and pi,pi interactions in the solid-state structure of a butadiynylene-linked bis(iodoperfluoroarene)}, journal = {CrystEngComm}, volume = {15}, year = {2013}, month = {2013}, pages = {3097 - 3101}, abstract = {

The solid-state structures of a butadiynylene-linked bidentate halogen bond donor, both as a single component and as a co-crystal with tetra-n-butylammonium iodide, are discussed. Solution-phase binding data indicate that this donor, which possesses only a single degree of conformational freedom, interacts with halides in a 1 : 1 stoichiometry through a convergent binding mode. In contrast, it forms a zigzag-type chain with iodide in the solid state. The X-ray crystallographic data enable detailed studies of the changes in molecular structure and supramolecular organization that accompany the formation of a halogen-bonded network.

}, url = {http://dx.doi.org/10.1039/C2CE26751A}, author = {Walter, Sebastian M. and Sarwar, Mohammed G. and Chudzinski, Michael G. and Herdtweck, Eberhardt and Lough, Alan J. and Huber, Stefan M. and Taylor, Mark S.} } @article {97, title = {Halogen bonding: from self-assembly to materials and biomolecules}, journal = {CrystEngComm}, volume = {15}, year = {2013}, month = {2013}, pages = {3057 - 3057}, url = {http://dx.doi.org/10.1039/C3CE90042H}, author = {Pennington, William T. and Resnati, Giuseppe and Taylor, Mark S.} } @article {96, title = {Halogen bonding in solution: thermodynamics and applications}, journal = {Chemical Society Reviews}, volume = {42}, year = {2013}, month = {2013}, pages = {1667 - 1680}, abstract = {

Halogen bonds are noncovalent interactions in which covalently bound halogens act as electrophilic species. The utility of halogen bonding for controlling self-assembly in the solid state is evident from a broad spectrum of applications in crystal engineering and materials science. Until recently, it has been less clear whether, and to what extent, halogen bonding could be employed to influence conformation, binding or reactivity in the solution phase. This tutorial review summarizes and interprets solution-phase thermodynamic data for halogen bonding interactions obtained over the past six decades and highlights emerging applications in molecular recognition, medicinal chemistry and catalysis.

}, isbn = {0306-0012}, url = {http://dx.doi.org/10.1039/C2CS35213C}, author = {Beale, Thomas M. and Chudzinski, Michael G. and Sarwar, Mohammed G. and Taylor, Mark S.} } @article {77, title = {Organoboron Acids and Their Derivatives as Catalysts for Organic Synthesis}, journal = {ACS Catalysis}, volume = {3}, year = {2013}, month = {2013/05/03}, pages = {945 - 962}, url = {http://dx.doi.org/10.1021/cs4000848}, author = {Dimitrijevi{\'c}, Elena and Taylor, Mark S.} } @article {91, title = {Regioselective silylation of pyranosides using a boronic acid/Lewis base co-catalyst system}, journal = {Organic \& Biomolecular Chemistry}, volume = {11}, year = {2013}, month = {2013}, pages = {5409 - 5412}, abstract = {

The combination of a boronic acid and a Lewis base, both employed in substoichiometric amounts, enables the regioselective silylation of cis-diol groups in alkylpyranoside substrates. The proposed mode of activation involves the formation of a tetracoordinate adduct that displays enhanced nucleophilicity at the boron-bound alkoxide groups.

}, isbn = {1477-0520}, url = {http://dx.doi.org/10.1039/C3OB40981C}, author = {Lee, Doris and Taylor, Mark S.} } @article {105, title = {Structure and energetics of gas phase halogen-bonding in mono-, bi-, and tri-dentate anion receptors as studied by BIRD}, journal = {Physical Chemistry Chemical Physics}, volume = {15}, year = {2013}, month = {2013}, pages = {7638 - 7647}, abstract = {

Complexes of mono-, bi- (RB), and tridentate (RT) receptors with a range of anions (Cl-, Br-, I-, NO3-, H2PO4-, HSO4-, and tosylate (TsO-)) have been studied in the gas phase by both experimental and theoretical methods. Temperature dependent blackbody infrared radiative dissociation (BIRD) experiments were performed on complexes of C8F17I with Br- and I-, RB with I-, NO3-, HSO4-, H2PO4-, and TsO-, and RT with I-, HSO4- and TsO- and the observed Arrhenius parameters are reported here. Master equation modeling of the BIRD kinetics data was carried out to determine threshold dissociation energies. Geometry optimizations and thermochemistry calculations were performed using the B3LYP/6-31+G(d,p) level of theory. Additional single point energies were calculated using MP2/6-311++G(2d,p). Results were examined in terms of the binding order of various anions as well as the added binding strength from additional halogen bonding (XB) interactions. The relative binding energies of ions were generally consistent with the ordering previously reported from solution phase experiments; however, the relatively strong binding of H2PO4- to the bidentate recepor contrasted the solution phase observation of oxoanions having weaker interactions when compared to halides. An increase in the energy required to remove the same anion from the tridentate receptor when compared to the bidentate and monodentate receptors is explained as being due to the increase in halogen bonding interactions. The possibility of mixed halogen and hydrogen bonded complexes were considered.

}, isbn = {1463-9076}, url = {http://dx.doi.org/10.1039/C3CP00105A}, author = {Gillis, Elizabeth A. L. and Demireva, Maria and Sarwar, Mohammed G. and Chudzinski, Michael G. and Taylor, Mark S. and Williams, Evan R. and Fridgen, Travis D.} } @article {76, title = {Structure{\textendash}Activity Relationships for Anion-Responsive Poly(squaramides): Support for an Analyte-Induced Noncovalent Polymer Cross-Linking Mechanism}, journal = {Macromolecules}, volume = {46}, year = {2013}, month = {2013/08/27}, pages = {6439 - 6450}, isbn = {0024-9297}, url = {http://dx.doi.org/10.1021/ma401263q}, author = {Rostami, Ali and Gu{\'e}rin, G{\'e}rald and Taylor, Mark S.} } @article {78, title = {Synthesis of Cardiac Glycoside Analogs by Catalyst-Controlled, Regioselective Glycosylation of Digitoxin}, journal = {Organic Letters}, volume = {15}, year = {2013}, month = {2013/03/15}, pages = {1358 - 1361}, isbn = {1523-7060}, url = {http://dx.doi.org/10.1021/ol4003042}, author = {Beale, Thomas M. and Taylor, Mark S.} } @inbook {111, title = {Borinic Acid, B,B-Bis(2,3,4,5,6-pentafluorophenyl)-}, booktitle = {Encyclopedia of Reagents for Organic Synthesis}, year = {2012}, publisher = {John Wiley \& Sons, Ltd}, organization = {John Wiley \& Sons, Ltd}, isbn = {9780470842898}, url = {http://dx.doi.org/10.1002/047084289X.rn01403}, author = {Lee, Doris and Taylor, Mark S.} } @article {101, title = {Catalyst-Controlled Regioselective Reactions of Carbohydrate Derivatives}, journal = {Synthesis}, volume = {44}, year = {2012}, month = {11/2012}, pages = {3421-3431}, isbn = {0039-7881}, author = {Lee, Doris and Taylor, Mark S.} } @article {80, title = {Correlations between Computation and Experimental Thermodynamics of Halogen Bonding}, journal = {The Journal of Organic Chemistry}, volume = {77}, year = {2012}, month = {2012/04/06}, pages = {3483 - 3491}, isbn = {0022-3263}, url = {http://dx.doi.org/10.1021/jo300279m}, author = {Chudzinski, Michael G. and Taylor, Mark S.} } @article {107, title = {Polymers for Anion Recognition and Sensing}, journal = {Macromol. Rapid Commun.}, volume = {33}, year = {2012}, month = {2012}, pages = {21 - 34}, abstract = {

In biological systems, the selective and high-affinity recognition of anionic species is accomplished by macromolecular hosts (anion-binding proteins) that have been {\textquotedblleft}optimized{\textquotedblright} through evolution. Surprisingly, it is only recently that chemists have systematically attempted to develop anion-responsive synthetic macromolecules for potential applications in medicine, national security, or environmental monitoring. Recent results indicating that unique features of polymeric systems such as signal amplification, multivalency, and cooperative behavior may be exploited productively in the context of anion recognition and sensing are documented. The wide variety of interactions{\textemdash}including Lewis acid/base, ion-pairing, and hydrogen bonding{\textemdash}that have been employed for this purpose is reflected in the structural diversity of anion-responsive macromolecules identified to date.

}, keywords = {anions, chemical sensors, Fluorescence, molecular recognition, polymers, supramolecular chemistry}, isbn = {1521-3927}, url = {http://dx.doi.org/10.1002/marc.201100528}, author = {Rostami, Ali and Taylor, Mark S.} } @article {79, title = {Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkylation of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies}, journal = {Journal of the American Chemical Society}, volume = {134}, year = {2012}, month = {2012/05/16}, pages = {8260 - 8267}, isbn = {0002-7863}, url = {http://dx.doi.org/10.1021/ja302549c}, author = {Lee, Doris and Williamson, Caitlin L. and Chan, Lina and Taylor, Mark S.} } @article {142, title = {Anion Detection by a Fluorescent Poly(squaramide): Self-Assembly of Anion-Binding Sites by Polymer Aggregation}, journal = {Angew. Chem. Int. Ed.}, volume = {50}, year = {2011}, month = {2011}, pages = {2059 - 2062}, keywords = {aggregation, anions, molecular recognition, polymers, self-assembly}, isbn = {1521-3773}, url = {http://dx.doi.org/10.1002/anie.201006884}, author = {Rostami, Ali and Wei, Chu Jun and Gu{\'e}rin, G{\'e}rald and Taylor, Mark S.} } @article {82, title = {Anion Receptors Composed of Hydrogen- and Halogen-Bond Donor Groups: Modulating Selectivity With Combinations of Distinct Noncovalent Interactions}, journal = {Journal of the American Chemical Society}, volume = {133}, year = {2011}, month = {2011/07/13}, pages = {10559 - 10567}, isbn = {0002-7863}, url = {http://pubs.acs.org/doi/abs/10.1021/ja202096f}, author = {Chudzinski, Michael G. and McClary, Corey A. and Taylor, Mark S.} } @article {84, title = {Borinic Acid-Catalyzed Regioselective Acylation of Carbohydrate Derivatives}, journal = {Journal of the American Chemical Society}, volume = {133}, year = {2011}, month = {2011/03/23}, pages = {3724 - 3727}, isbn = {0002-7863}, url = {http://dx.doi.org/10.1021/ja110332r}, author = {Lee, Doris and Taylor, Mark S.} } @article {108, title = {Borinic Acids: A Neglected Class of Organoboron Compounds for Recognition of Diols in Aqueous Solution}, journal = {Australian Journal of Chemistry}, volume = {64}, year = {2011}, month = {2011}, pages = {1466 - 1469}, abstract = {

Association constants between diphenylborinic acid and representative analytes capable of reversible two-point covalent binding (diols, catechols, and hydroxy acids) were determined using an indicator-displacement assay. Unlike boronic acids, which have been studied in great detail as receptors for diols and related compounds, borinic acids have effectively been ignored as candidates for such applications. The results of this study indicate that diphenylborinic acid displays high affinity for certain analytes of this type in aqueous solution. Of particular interest are differences between the selectivity of the borinic acid and that of a boronic acid of similar pKa towards the series of analytes studied: the borinic acid displays an unusually high level of discrimination for catechols over carbohydrates. The distinct selectivity observed, and the unique opportunities for steric and electronic tuning of diarylborinic acids, suggest that these compounds hold significant potential for applications in aqueous-phase molecular recognition.

}, url = {http://dx.doi.org/10.1071/CH11294}, author = {Chudzinski, Michael G. and Chi, Yuechuan and Taylor, Mark S.} } @article {104, title = {Burgenstock 2011: A stereochemical sojourn}, journal = {Nat Chem}, volume = {3}, year = {2011}, month = {2011/09//print}, pages = {660 - 662}, isbn = {1755-4330}, url = {http://dx.doi.org/10.1038/nchem.1133}, author = {Taylor, Mark S.} } @article {109, title = {Carbon{\textendash}carbon bond-forming reactions of α-carbonyl carbocations: exploration of a reversed-polarity equivalent of enolate chemistry}, journal = {Tetrahedron}, volume = {67}, year = {2011}, month = {2011/9/30/}, pages = {7586 - 7592}, abstract = {

Carbon{\textendash}carbon bond-forming reactions of putative α-carbonyl carbocation intermediates generated by Lewis acid- or silver-promoted ionizations of toluenesulfonate or halide leaving groups are described. This under-exploited mode of reactivity represents an {\textquoteleft}umpolung{\textquoteright} of conventional enolate chemistry, and enables C{\textendash}C bond construction in both intra- and intermolecular contexts. Attempts to develop diastereoselective variants of this process using chiral ester and oxazolidinone-based auxiliaries are discussed.

}, keywords = {Allylation, Carbocations, Friedel{\textendash}Crafts reaction, Lactams, Umpolung reactivity}, isbn = {0040-4020}, url = {http://www.sciencedirect.com/science/article/pii/S0040402011011148}, author = {Lai, Ping-Shan and Dubland, Joshua A. and Sarwar, Mohammed G. and Chudzinski, Michael G. and Taylor, Mark S.} } @article {81, title = {Regioselective Activation of Glycosyl Acceptors by a Diarylborinic Acid-Derived Catalyst}, journal = {Journal of the American Chemical Society}, volume = {133}, year = {2011}, month = {2011/09/07}, pages = {13926 - 13929}, isbn = {0002-7863}, url = {http://dx.doi.org/10.1021/ja2062715}, author = {Gouliaras, Christina and Lee, Doris and Chan, Lina and Taylor, Mark S.} } @article {83, title = {Regioselective Alkylation of Carbohydrate Derivatives Catalyzed by a Diarylborinic Acid Derivative}, journal = {Organic Letters}, volume = {13}, year = {2011}, month = {2011/06/17}, pages = {3090 - 3093}, isbn = {1523-7060}, url = {http://dx.doi.org/10.1021/ol200990e}, author = {Chan, Lina and Taylor, Mark S.} } @article {94, title = {Measurements of weak halogen bond donor abilities with tridentate anion receptors}, journal = {Chemical Communications}, volume = {46}, year = {2010}, month = {2010}, pages = {9025 - 9027}, abstract = {

The chelate effect of a tridentate receptor is exploited to determine halogen bonding association constants that vary by several orders of magnitude, including interactions of weak donors for which thermodynamic data were not previously available. Free energy relationships with computed and experimental properties hold over this wide range of donors. The strengths of iodine- and bromine-based halogen bonds, CH-anion and anion-arene interactions are compared.

}, isbn = {1359-7345}, url = {http://dx.doi.org/10.1039/C0CC03347B}, author = {Dimitrijevi{\'c}, Elena and Kvak, Olga and Taylor, Mark S.} } @article {85, title = {N,N'-Diarylsquaramides: General, High-Yielding Synthesis and Applications in Colorimetric Anion Sensing}, journal = {The Journal of Organic Chemistry}, volume = {75}, year = {2010}, month = {2010/06/18}, pages = {3983 - 3992}, isbn = {0022-3263}, url = {http://dx.doi.org/10.1021/jo100104g}, author = {Rostami, Ali and Colin, Alexis and Li, Xiao Yu and Chudzinski, Michael G. and Lough, Alan J. and Taylor, Mark S.} } @article {102, title = {Preparation of Substituted Oxazolesby Ritter Reactions of alpha-Oxo Tosylates}, journal = {Synthesis}, volume = {2010}, year = {2010}, month = {04/2010}, pages = {1449-1452}, isbn = {0039-7881}, author = {Lai, Ping-Shan and Taylor, Mark S.} } @article {86, title = {Thermodynamics of Halogen Bonding in Solution: Substituent, Structural, and Solvent Effects}, journal = {Journal of the American Chemical Society}, volume = {132}, year = {2010}, month = {2010/02/10}, pages = {1646 - 1653}, isbn = {0002-7863}, url = {http://dx.doi.org/10.1021/ja9086352}, author = {Sarwar, Mohammed G. and Dragisic, Bojan and Salsberg, Lee J. and Gouliaras, Christina and Taylor, Mark S.} } @article {141, title = {A Tridentate Halogen-Bonding Receptor for Tight Binding of Halide Anions}, journal = {Angewandte Chemie International Edition}, volume = {49}, year = {2010}, month = {2010}, pages = {1674 - 1677}, keywords = {anions, halogens, molecular recognition, noncovalent interactions, supramolecular chemistry}, isbn = {1521-3773}, url = {http://dx.doi.org/10.1002/anie.200906488}, author = {Sarwar, Mohammed G. and Dragisic, Bojan and Sagoo, Sandeep and Taylor, Mark S.} } @article {67, title = {Boron-Catalyzed Direct Aldol Reactions of Pyruvic Acids}, journal = {Organic Letters}, volume = {11}, year = {2009}, month = {2009/12/03}, pages = {5486 - 5489}, isbn = {1523-7060}, url = {http://dx.doi.org/10.1021/ol902322r}, author = {Lee, Doris and Newman, Stephen G. and Taylor, Mark S.} }