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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 845-854

Reaction of alcohols and silyl ethers in the presence of an indium/silicon-based catalyst system: Deoxygenation and allyl substitution

Akio Baba, Makoto Yasuda, Yoshihiro Nishimoto, Takahiro Saito and Yoshiyuki Onishi

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

Abstract: An In(III)/Si catalyst system effects the direct allyl substitution of alcohols and silyl ethers under mild conditions. A deoxygenation of alcohols is also promoted by InCl3 catalyst. This method requires no pretreatment or protection of hydroxy groups or deprotection of siloxy groups. The completion of the catalytic allylation depends on the low oxophilicity and high halophilicity of In(III) halide species, and other representative Lewis acids such as AlCl3 and BF3 have no catalytic activity for the allylations. The oxophilicity and halophilicity are also demonstrated by NMR studies.