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

Research output: Contribution to journalArticle

77 Citations (Scopus)

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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Copper
esters
Esters
copper
Iodides
iodides
Ligands
catalysts
ligands
Catalysts
N,N-dimethylaniline

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Gurung, Santosh K. ; Thapa, Surendra ; Kafle, Arjun ; Dickie, Diane A. ; Giri, Ramesh. / Copper-catalyzed suzuki-miyaura coupling of arylboronate esters : Transmetalation with (PN)CuF and identification of intermediates. In: Organic Letters. 2014 ; Vol. 16, No. 4. pp. 1264-1267.
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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.",
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Copper-catalyzed suzuki-miyaura coupling of arylboronate esters : Transmetalation with (PN)CuF and identification of intermediates. / Gurung, Santosh K.; Thapa, Surendra; Kafle, Arjun; Dickie, Diane A.; Giri, Ramesh.

In: Organic Letters, Vol. 16, No. 4, 21.02.2014, p. 1264-1267.

Research output: Contribution to journalArticle

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T1 - Copper-catalyzed suzuki-miyaura coupling of arylboronate esters

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AU - Gurung, Santosh K.

AU - Thapa, Surendra

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AU - Giri, Ramesh

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AB - 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.

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