Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 845-854
doi:10.1351/pac200880050845
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.
Keywords: alcohol; combined system; direct substitution; indium; silicon; silyl ether.
*Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194.
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