Highly efficient and practical phosphoramidite-copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles

被引：140

作者：

Zhang, ZJ ^{[1
]}

Mao, JC ^{[1
]}

Zhu, D ^{[1
]}

Wu, F ^{[1
]}

Chen, HL ^{[1
]}

Wan, BS ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

来源：

TETRAHEDRON | 2006年 / 62卷 / 18期

关键词：

amination; phosphoramidite; heteroaryl bromide; copper; catalysis;

D O I：

10.1016/j.tet.2006.02.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient copper-catalyzed system using phosphoramidite as ligands was applied to N-arylation of alkylamines and N(H)-heterocycles with aryl iodides and heteroaryl bromides. The reactions were carried out in relative mild conditions and good to excellent yields were obtained. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4435 / 4443

页数：9

共 49 条

[21] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[22]

INCOLAOU KC, 2005, ANGEW CHEM INT EDIT, V44, P4442

[23] Aminoarenethiolate-copper(I)-catalyzed amination of aryl bromides [J].

Jerphagnon, T ;

van Klink, GPM ;

de Vries, JG ;

van Koten, G .

ORGANIC LETTERS, 2005, 7 (23) :5241-5244

[24] Selective amination of polyhalopyridines catalyzed by a palladium-xantphos complex [J].

Ji, JG ;

Li, T ;

Bunnelle, WH .

ORGANIC LETTERS, 2003, 5 (24) :4611-4614

[25] A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles [J].

Klapars, A ;

Antilla, JC ;

Huang, XH ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7727-7729

[26] A general and efficient copper catalyst for the amidation of aryl halides [J].

Klapars, A ;

Huang, XH ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7421-7428

[27] Mild copper-catalyzed N-arylation of azaheterocycles with aryl halides [J].

Kuil, M ;

Bekedam, EK ;

Visser, GM ;

van den Hoogenband, A ;

Terpstra, JW ;

Kamer, PCJ ;

van Leeuwen, PWNM ;

van Strijdonck, GPF .

TETRAHEDRON LETTERS, 2005, 46 (14) :2405-2409

[28] Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines [J].

Kwong, FY ;

Buchwald, SL .

ORGANIC LETTERS, 2003, 5 (06) :793-796

[29] Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere [J].

Kwong, FY ;

Klapars, A ;

Buchwald, SL .

ORGANIC LETTERS, 2002, 4 (04) :581-584

[30] Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation [J].

Ley, SV ;

Thomas, AW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5400-5449

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