N-Arylation of nitrogen heterocycles with aryl halides and arylboronic acids catalyzed by cellulose supported copper(0)

被引：93

作者：

Reddy, K. Rajender ^{[1
]}

Kumar, Nadakuditi S. ^{[1
]}

Sreedhar, B. ^{[1
]}

Kantam, M. Lakshmi ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2006年 / 252卷 / 1-2期

关键词：

copper catalyst; cellulose support; C-N coupling; imidazole; aryl halides; arylboronic acids;

D O I：

10.1016/j.molcata.2006.02.053

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Cellulose supported copper(0) catalyst was prepared and employed for the N-arylation of nitrogen heterocycles with a variety of aryl halides and arylboronic acids to afford the corresponding coupled products in good to excellent yields without using external ligands or additives as promoters. The catalyst was recovered by simple filtration and reused for several cycles. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：136 / 141

页数：6

共 41 条

[1]

Alvarado P. L., 1995, J ORG CHEM, V60, P5678

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

Antilla, JC ;

Buchwald, SL .

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

[3] The chemistry of pentavalent organobismuth reagents .14. Recent advances in the copper-catalyzed phenylation of amines. [J].

Arnauld, T ;

Barton, DHR ;

Doris, E .

TETRAHEDRON, 1997, 53 (12) :4137-4144

[4] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[5] Design and evolution of copper apatite catalysts for N-arylation of heterocycles with chloro- and fluoroarenes [J].

Choudary, BM ;

Sridhar, C ;

Kantam, ML ;

Venkanna, GT ;

Sreedhar, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9948-9949

[6] 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

[7] 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

[8] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].

Collman, JP ;

Zhong, M .

ORGANIC LETTERS, 2000, 2 (09) :1233-1236

[9] Cellulose beads: a new versatile solid support for microwave-assisted synthesis. Preparation of pyrazole and isoxazole libraries [J].

De Luca, L ;

Giacomelli, G ;

Porcheddu, A ;

Salaris, M ;

Taddei, M .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (04) :465-471

[10] Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].

Evans, DA ;

Katz, JL ;

West, TR .

TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940

← 1 2 3 4 5 →