Alkane carbon-hydrogen bond functionalization with (NHC)MCl precatalysts (M = Cu, Au; NHC=N-heterocyclic carbene)

Facile alkane functionalization by means of the insertion of :CHCO2Et, from ethyl diazoacetate, into carbon-hydrogen bonds mediated by catalytic amounts of (NHC)MCI (NHC = N-heterocyclic ligand; M = Cu, Au) and a halide scavenger MX has been achieved. This chemistry includes the insertion of the carbene fragment into alkane primary positions with Cu- and Au-based catalysts. The nature of the counterion X and of the NHC ligand have a significant effect on the overall yields and regioselectivity of the reaction.