ol500310u_si_004.cif (95.18 kB)

Copper-Catalyzed Suzuki–Miyaura Coupling of Arylboronate Esters: Transmetalation with (PN)CuF and Identification of Intermediates

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posted on 21.02.2014, 00:00 by Santosh K. Gurung, Surendra Thapa, Arjun Kafle, Diane A. Dickie, Ramesh Giri
An efficient CuI-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.