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

Santosh K. Gurung, Surendra Thapa, Arjun Kafle, Diane A. Dickie and Ramesh Giri*

*Department of Chemistry & Chemical Biology, University of New Mexico, Albuquerque, New Mexico 87131, United States, Email: rgiriunm.edu

S. K. Gurung, S. Thapa, A. Kafle, D. A. Dickie, R. Giri, Org. Lett., 2014, 16, 1264-1267.

DOI: 10.1021/ol500310u (free Supporting Information)


Abstract

An efficient CuI-catalyzed Suzuki-Miyaura reaction for the coupling of aryl- and heteroarylboronate esters with aryl and heteroaryl iodides proceeds at low catalyst loadings and for aryl-heteroaryl and heteroaryl-heteroaryl couplings under ligand-free conditions. Mechanistic studies demonstrated that [(L)CuF]2 is the species that undergoes transmetalation with arylboronate esters.

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Key Words

Suzuki coupling, Biaryls


ID: J54-Y2014