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

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journal contribution
posted on 16.06.2004, 00:00 by Makoto Yasuda, Satoshi Yamasaki, Yoshiyuki Onishi, Akio Baba
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.