A Novel B(C₆F₅)₃-Catalyzed Reduction of Alcohols and Cleavage of Aryl and Alkyl Ethers with Hydrosilanes

Vladimir Gevorgyan*, Michael Rubin, Sharonda Benson, Jian-Xiu Liu and Yoshinori Yamamoto*

*University of Illinois at Chicago, 845 Taylor Street, Chicago, Illinois 60607-7061, USA, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Email: vladutdallas.edu

V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto, J. Org. Chem., 2000, 65, 6179-6168.

DOI: 10.1021/jo000726d

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Abstract

Primary alcohols and ethers were effectively reduced to the corresponding hydrocarbons by HSiEt₃ in the presence of catalytic amounts of B(C₆F₅)₃. Secondary alkyl ethers are cleaved under similar reaction conditions to produce silyl ethers or alcohols upon subsequent deprotection with TBAF. The following relative reactivity order of substrates was found:  primary >> secondary > tertiary.

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Key Words

deoxygenation, silyl ethers, triethylsilane, cleavage of ethers

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ID: J42-Y2000