@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}, url = {http://dx.doi.org/10.1039/D1CC05124E}, 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 {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 {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 {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 {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 {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.} }