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

Yoshiyuki Onishi, Daigo Ogawa, Makoto Yasuda 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

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

DOI: 10.1021/ja0283246

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Abstract

An indium(III) hydroxide-catalyzed reaction of carbonyls and chlorodimethylsilane afforded the corresponding deoxygenative chlorination products. Ester, nitro, cyano, or halogen groups were not affected during the reaction course. Typical Lewis acids such as TiCl₄, AlCl₃, and BF₃·OEt₂ showed no catalytic activity. The reaction mechanism is discussed.

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

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

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Key Words

Chlorinations, Deoxygenations, Silanes, Indium

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ID: J48-Y2002-1360