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A Direct Reduction of Aliphatic Aldehyde, Acyl Chloride, Ester, and Carboxylic Functions into a Methyl Group

Vladimir Gevorgyan*, Michael Rubin, Jian-Xiu Liu and Yoshinori Yamamoto

*Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, Illinois 60607-7061, Email: vladuic.edu

V. Gevorgyan, M. Rubin, J.-X. Liu, Y. Yamamoto,  J. Org. Chem, 2000, 66, 1672-1675.

DOI: 10.1021/jo001258a (free Supporting Information)


Abstract

Aliphatic carboxyl derivatives (acids, acyl chlorides, esters) and aldehydes were efficiently reduced to the methyl group by HSiEt3 in the presence of catalytic amounts of B(C6F5)3. Aromatic carboxylic acids, as well as other carbonyl functional equivalents, underwent smooth partial reduction to the corresponding TES-protected benzylic alcohols in competition with a Friedel-Crafts-like alkylation decreasing the overall selectivity of the reduction process.

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Key Words

Deoxygenations, Alcohol Synthesis, Silyl Ethers, Triethylsilane


ID: J42-Y2001-570