Room-Temperature Catalytic Hydrodefluorination of C(sp3)-F Bonds

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J. Am. Chem. Soc., 127 (9), 2852 -2853, 2005. 10.1021/ja0426138 S0002-7863(04)02613-7
Web Release Date: February 8, 2005

Room-Temperature Catalytic Hydrodefluorination of C(sp³)-F Bonds

Valerie J. Scott, Remle Çelenligil-Çetin, and Oleg V. Ozerov*

Department of Chemistry, Brandeis University, MS015, 415 South Street, Waltham Massachusetts 02454

ozerov@brandeis.edu

Received December 8, 2004

Abstract:

Room-temperature catalytic hydrodefluorination of the strong C(sp³)-F bonds in benzotrifluorides and fluoropentane is catalyzed by Et₃Si[B(C₆F₅)₄] and uses Et₃SiH as the source of H. Ar-CF₃ compounds are converted to Ar-CH₃ and fluropentane to pentane. The reaction is thought to proceed via abstraction of F^- by Et₃Si[B(C₆F₅)₄], and the substituent effects are consistent with this hypothesis.

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