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, Ramesh Giri

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)1264-1267
Number of pages4
JournalOrganic Letters
Volume16
Issue number4
DOIs
StatePublished - Feb 21 2014

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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