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

doi:10.1021/ol500310u

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

Chemistry

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121 Scopus citations

Abstract

An efficient Cu^I-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 language	English (US)
Pages (from-to)	1264-1267
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	4
DOIs	https://doi.org/10.1021/ol500310u
State	Published - Feb 21 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Copper-catalyzed suzuki-miyaura coupling of arylboronate esters: Transmetalation with (PN)CuF and identification of intermediates",

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

T2 - Transmetalation with (PN)CuF and identification of intermediates

AU - Gurung, Santosh K.

AU - Thapa, Surendra

AU - Kafle, Arjun

AU - Dickie, Diane A.

AU - Giri, Ramesh

PY - 2014/2/21

Y1 - 2014/2/21

N2 - 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.

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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Copper-catalyzed suzuki-miyaura coupling of arylboronate esters: Transmetalation with (PN)CuF and identification of intermediates

Abstract

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