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

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.