Copper-catalyzed suzuki-miyaura coupling of arylboronate esters: Transmetalation with (PN)CuF and identification of intermediates

Article abstract of DOI:10.1021/ol500310u

An efficient Cu^I-catalyzed Suzuki-Miyaura reaction was developed for the coupling of aryl- and heteroarylboronate esters with aryl and heteroaryl iodides at low catalyst loadings (2 mol %). The reaction proceeds under ligand-free conditions for aryl-heteroaryl and heteroaryl-heteroaryl couplings. We also conducted the first detailed mechanistic studies by synthesizing [(PN-2)CuI]₂, [(PN-2)CuF]₂, and (PN-2)CuPh (PN-2 = o-(di-tert-butylphosphino)-N,N-dimethylaniline) and demonstrated that [(PN-2)CuF]₂ is the species that undergoes transmetalation with arylboronate esters.