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Direct Reduction of Alcohols: Highly Chemoselective Reducing System for Secondary or Tertiary Alcohols Using Chlorodiphenylsilane with a Catalytic Amount of Indium Trichloride

Makoto Yasuda, Yoshiyuki Onishi, Masako Ueba, Takashi Miyai and Akio Baba*

*Department of Molecular Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: babachem.eng.osaka-u.ac.jp

M. Yasuda, Y. Onishi, M. Ueba, T. Miyai, A. Baba, J. Org. Chem., 2001, 66, 7741-7744.

DOI: 10.1021/jo0158534 (free Supporting Information)


Abstract

A direct reduction of alcohols to the corresponding alkanes using chlorodiphenylsilane as hydride source in the presence of a catalytic amount of InCl3 showed high chemoselectivity for benzylic alcohols, secondary alcohols and tertiary alcohols while not reducing primary alcohols and functional groups that are readily reduced by standard methods such as esters, chloro, bromo, and nitro groups.

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proposed mechanism



Key Words

deoxygenations, silanes, indium


ID: J42-Y2001-190