Room-temperature catalytic hydrodefluorination of C(sp3)-F bonds

Valerie J Scott; Remle Celenligil-Cetin; Oleg V Ozerov

doi:10.1021/ja0426138

Room-temperature catalytic hydrodefluorination of C(sp3)-F bonds

J Am Chem Soc. 2005 Mar 9;127(9):2852-3. doi: 10.1021/ja0426138.

Authors

Valerie J Scott¹, Remle Celenligil-Cetin, Oleg V Ozerov

Affiliation

¹ Department of Chemistry, Brandeis University, MS015, 415 South Street, Waltham Massachusetts 02454, USA.

PMID: 15740111
DOI: 10.1021/ja0426138

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.