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

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• 作者：Santosh K. Gurung ; Surendra Thapa ; Arjun Kafle ; Diane A. Dickie ; Ramesh Giri
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 21, 2014
• 年：2014
• 卷：16
• 期：4
• 页码：1264-1267
• 全文大小：266K
• ISSN：1523-7052

文摘

An efficient Cu^I-catalyzed Suzuki鈥揗iyaura 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鈥揾eteroaryl and heteroaryl鈥揾eteroaryl 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.