Swift C-C bond insertion by a 12-electron palladium(0) surrogate

The selective activation of C-C bonds holds vast promise for catalysis. So far, research has been primarily directed at rhodium and nickel under harsh reaction conditions. Herein, we report C-C insertion reactions of a 12-electron palladium(0) surrogate stabilized by a cyclic(alkyl)(amino) carbene (CAAC) ligand. Benzonitrile (1), biphenylene (2), benzocyclobutenone (3), and naphtho[b]cyclopropene (4) were studied. These substrates allow elucidation of the effect of ring strain as well as hybridization encompassing sp3, sp2 and sp hybridized carbon atoms. All reactions proceed quantitatively at or below room temperature. This work therefore outlines perspectives for mild C-C bond functionalization catalysis. The selective activation of C-C bonds holds vast promise for catalysis.

Automated summary

This study reports on C-C insertion reactions of a 12-electron palladium(0) surrogate stabilized by a cyclic(alkyl)(amino) carbene (CAAC) ligand. Substrates including benzonitrile, biphenylene, benzocyclobutenone, and naphtho[b]cyclopropene were studied to elucidate the effect of ring strain and hybridization on the reactions. All reactions proceed quantitatively at or below room temperature, outlining perspectives for mild C-C bond functionalization catalysis.