Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C–H Borylation/Difluoromethylation

A process for the concurrent transfer of both the NHC ligand and the difluoromethyl group from [(SIPr)­Ag­(CF2H)] to PdX2 (X = Cl, OAc, and OPiv) for the preparation of [(SIPr)­Pd­(CF2H)­X] complexes is described. These complexes were air-stable and easily underwent transmetalation with aryl pinacol boronate/reductive elimination to generate ArCF2H in high yields. Based on this discovery, the first one-pot C–H borylation and difluoromethylation process for the preparation of difluoromethylated (hetero)­arenes was developed.