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Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkylation of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies

Doris Lee, Caitlin L. Williamson, Lina Chan and Mark S. Taylor*

*Department of Chemistry, University of Toronto, 80 St. George Street, Toronto ON M5S 3H6, Canada, Email: mtaylorchem.utoronto.ca

D. Lee, C. L. Williamson, L. Chan, M. S. Taylor, J. Am. Chem. Soc., 2012, 134, 8260-8267.

DOI: 10.1021/ja302549c (free Supporting Information)


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Abstract

Diarylborinic acid catalysis is an efficient and general method for selective acylation, sulfonylation, and alkylation of 1,2- and 1,3-diols. The efficiency, generality, and operational simplicity of this method are competitive with those of the broadly applied organotin-catalyzed reactions. A mechanism is suggested, in which a tetracoordinate borinate complex reacts with the electrophilic species in the turnover-limiting step of the catalytic cycle.

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Borinic Acid-Catalyzed Regioselective Acylation of Carbohydrate Derivatives

D. Lee, M. S. Taylor, J. Am. Chem. Soc., 2011, 133, 3724-3727.


Key Words

Sulfonates, Benzyl Ethers


ID: J48-Y2012-1430