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

被引：128

作者：

Gurung, Santosh K. ^{[1
]}

Thapa, Surendra ^{[1
]}

Kafle, Arjun ^{[1
]}

Dickie, Diane A. ^{[1
]}

Giri, Ramesh ^{[1
]}

机构：

[1] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 04期

关键词：

SECONDARY ALKYL BROMIDES; HETEROARYL BORONIC ACIDS; CROSS-COUPLINGS; ORGANOBORON COMPOUNDS; ROOM-TEMPERATURE; ARYL HALIDES; IODIDES; HETEROCYCLES; COMPLEXES; CHEMISTRY;

D O I：

10.1021/ol500310u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1264 / 1267

页数：4

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