Indium-Catalyzed Direct Chlorination of Alcohols Using Chlorodimethylsilane−Benzil as a Selective and Mild System

Makoto Yasuda, Satoshi Yamasaki, Yoshiyuki Onishi, and Akio Baba*
Department of Molecular Chemistry and Handai Frontier Research Center, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
J. Am. Chem. Soc., 2004, 126 (23), pp 7186–7187
DOI: 10.1021/ja048688t
Publication Date (Web): May 22, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, baba@chem.eng.osaka-u.ac.jp

Abstract

Abstract Image

The InCl3-catalyzed reaction of alcohols with chlorodimethylsilane (HSiMe2Cl) in the presence of benzil gave the corresponding organic chlorides under mild conditions. Benzil significantly changes the reaction course because the reducing product through dehydroxyhydration was obtained in the absence of benzil. The secondary or tertiary alcohols were effectively chlorinated. The substrates bearing acid-sensitive functional groups were also applied to this system. The highly selective chlorination of the tertiary site was observed in the competitive reaction between tertiary and primary alcohols. The highly coordinated hydrosilane generated from benzil and HSiMe2Cl is an important intermediate.

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History

  • Published In Issue June 16, 2004
  • Received March 8, 2004

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