Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF<sub>2</sub>H)(X) and Its Application in One-Pot C–H Borylation/Difluoromethylation
Haiwei Zhao, Simon A. Herbert, Tom Kinzel, Wei Zhang, Qilong Shen
Abstract
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.
Topics & Concepts
BorylationChemistryTransmetalationArylPalladiumPinacolMedicinal chemistryLigand (biochemistry)Reductive eliminationStereochemistryCombinatorial chemistryCatalysisOrganic chemistryBiochemistryAlkylReceptorFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysis