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, Email: babachem.eng.osaka-u.ac.jp

M. Yasuda, S. Yamasaki, Y. Onishi, A. Baba, J. Am. Chem. Soc., 2004, 126, 7186-7187.

DOI: 10.1021/ja048688t

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Abstract

An efficient InCl₃-catalyzed reaction of secondary, tertiary and benzylic alcohols with chlorodimethylsilane in the presence of benzil gave the corresponding organic chlorides under mild conditions. In the absence of benzil, the reducing products through dehydroxyhydration were obtained.

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Direct Conversion of Carbonyl Compounds into Organic Halides: Indium(III) Hydroxide-Catalyzed Deoxygenative Halogenation Using Chlorodimethylsilane

Y. Onishi, D. Ogawa, M. Yasuda, A. Baba, J. Am. Chem. Soc., 2002, 124, 13690-13691.

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Key Words

alkyl chlorides, benzyl chlorides

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ID: J48-Y2004-1510