C(sp3)–F, C(sp2)–F and C(sp3)–H bond activation at silicon(ii) centers

Abstract

Silylene [PhC(NtBu)₂SiN(SiMe₃)₂] (1) cleaves the C(sp³)–H and C–F bonds of acetophenone and 1,1,1-trifluoroacetophenone, respectively, under mild conditions. The reaction is initiated via a nucleophilic attack from the oxygen to the silicon atom followed by C–F/H bond cleavage. The scope of C–F bond activation has further been extended with C₆F₆ and C₆F₅CF₃.