Metal free and selective activation of one C–F bond in a bound CF3 group

Abstract

The first metal free selective C–F bond activation of a CF₃ group was observed with N-heterocyclic silylenes [PhC(NtBu)₂SiCl] (1) and [CH{(CCH₂)(CMe)(2,6-iPr₂C₆H₃N)₂}Si] (2) with PhNC(CF₃)₂. The reaction proceeds in a 1 : 1 molar ratio to yield the mono C–F bond activated products 3 and 4 with each containing a CF₂ group. Both the reactions proceed through an unprecedented selective activation of one of the C–F bonds rather than forming the [1+2] cycloaddition product containing the three-membered SiNC rings.