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

[1]

ANG BH, 1999, J ORGANOMET CHEM, V576, P125

[2] Copper-catalyzed coupling of arylboronic acids and amines [J].

Antilla, JC ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (13) :2077-2079

[3] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[4] Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].

Antilla, JC ;

Baskin, JM ;

Barder, TE ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587

[5] Catalytic amination of 5-iodouracil derivatives [J].

Arterburn, JB ;

Pannala, M ;

Gonzalez, AM .

TETRAHEDRON LETTERS, 2001, 42 (08) :1475-1477

[6]

Buckingham J, 1994, Dictionary of natural products, V1

[7] Efficient Pd-catalyzed amination of heteroaryl halides [J].

Charles, MD ;

Schultz, P ;

Buchwald, SL .

ORGANIC LETTERS, 2005, 7 (18) :3965-3968

[8] Polymer-supported copper complex for C-N and C-O cross-coupling reactions with aryl boronic acids [J].

Chiang, GCH ;

Olsson, T .

ORGANIC LETTERS, 2004, 6 (18) :3079-3082

[9] Catalytic activities of Cu(II) complexes with nitrogen-chelating bidentate ligands in the coupling of imidazoles with arylboronic acids [J].

Collman, JP ;

Zhong, M ;

Zhang, C ;

Costanzo, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7892-7897

[10] The [Cu(OH)•TMEDA]2Cl2-catalyzed coupling of arylboronic acids with imidazoles in water [J].

Collman, JP ;

Zhong, M ;

Zeng, L ;

Costanzo, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1528-1531

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