Catalysis
We aim to develop new modes of catalytic reactivity, to study their mechanisms, and to use them to solve problems in organic synthesis. An area of focus is the discovery of organoboron-catalyzed reactions. We have shown that borinic acids can be used to activate diol groups towards reactions with electrophiles. This activation mode provides a way to achieve site-selective reactions of carbohydrates, including regio- and stereoselective glycosylation. Synthetic catalysts that can influence the reactivity of sugars will provide new opportunities to efficiently generate complex glycosides for use as biological probes or prospective therapeutic agents.
Representative publications:
Taylor, MS "Catalysis based on reversible interactions of organoboron compounds" Acc. Chem. Res. 2015, 48, 295.
D'Angelo K, Taylor, MS "Borinic acid catalyzed stereo- and regioselective couplings of glycosyl methanesulfonates" J. Am. Chem. Soc. 2016, 138, 11058.
Molecular Recognition
We use organic synthesis and physical organic chemistry to gain insight into poorly understood types of noncovalent interactions. We are particularly interested in halogen bonding and chalcogen bonding, interactions of Lewis bases with electron-deficient, covalently bonded Group 17 or Group 16 elements. We have determined the strengths of these interactions in solution and have used empirical models and computational chemistry to interpret the results. Exploring applications of these interactions in solution-phase host-guest chemistry and self-assembly is an area of ongoing research in the group.
Representative publications:
Beale TM, Chudzinski MG, Sarwar MG, Taylor MS "Halogen bonding in solution: thermodynamics and applications" Chem. Soc. Rev. 2013, 42, 1667.
Garrett GE, Gibson GL, Straus RN, Seferos DS, Taylor MS "Chalcogen bonding in solution: interactions of benzotellurazidazoles with anionic and uncharged Lewis bases" J. Am. Chem. Soc. 2015, 137, 4126.