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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:

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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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

ID: J42-Y2000