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Reductive Etherification via Anion-Binding Catalysis

Chenfei Zhao, Christopher A. Sojdak , Wazo Myint and Daniel Seidel*

*Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States, Email: seidelchem.ufl.edu

C. Zhao, C. A. Sojdak, W. Myint, D. Seidel, J. Am. Chem. Soc., 2017, 139, 10224-10227.

DOI: 10.1021/jacs.7b05832 (free Supporting Information)


Abstract

A readily accessible thiourea organocatalyst catalyzes reductive condensations of alcohols with aldehydes/ketones to provide ethers without homocoupling of the carbonyl component in the presence of HCl and 1,1,3,3-tetramethyldisiloxane as a convenient reducing reagent. This strategy is applicable to challenging substrate combinations and exhibits functional group tolerance.

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Key Words

reductive etherification, 1,1,3,3-tetramethyldisiloxane, organocatalysis


ID: J48-Y2017