CuO Nanoparticles Catalyzed C-N, C-O, and C-S Cross-Coupling Reactions: Scope and Mechanism

被引：376

作者：

Jammi, Suribabu ^{[1
]}

Sakthivel, Sekarpandi ^{[1
]}

Rout, Laxmidhar ^{[1
]}

Mukherjee, Tathagata ^{[1
]}

Mandal, Santu ^{[1
]}

Mitra, Raja ^{[1
]}

Saha, Prasenjit ^{[1
]}

Punniyamurthy, Tharmalingam ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 05期

关键词：

EFFICIENT COPPER CATALYST; ARYL HALIDES; PALLADIUM NANOPARTICLES; TRANSITION-METAL; BOND FORMATION; AMINO-ACID; REDUCTIVE ELIMINATION; GOLDBERG REACTIONS; PHOSPHINE-LIGANDS; AEROBIC OXIDATION;

D O I：

10.1021/jo8024253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.

引用

页码：1971 / 1976

页数：6

共 139 条

[1] An improved method for the palladium-catalyzed amination of aryl iodides [J].

Ali, MH ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2560-2565

[2] An improved cu-based catalyst system for the reactions of alcohols with aryl halides [J].

Altman, Ryan A. ;

Shafir, Alexandr ;

Choi, Alice ;

Lichtor, Phillip A. ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :284-286

[3] Copper-catalyzed N-arylation of imidazoles and benzimidazoles [J].

Altman, Ryan A. ;

Koval, Erica D. ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6190-6199

[4] 4,7-Dimethoxy-1,10-phenanthroline:: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles [J].

Altman, Ryan A. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2006, 8 (13) :2779-2782

[5] 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

[6] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].

Aranyos, A ;

Old, DW ;

Kiyomori, A ;

Wolfe, JP ;

Sadighi, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378

[7] Effect of substitution of [Pd(PPh3)4] by related compounds as catalysts in reactions of organic syntheses [J].

Barbieri, Roberto S. ;

Bellato, C. R. ;

Dias, A. K. C. ;

Massabni, A. C. .

CATALYSIS LETTERS, 2006, 109 (3-4) :171-174

[8] Copper-catalyzed synthesis of vinyl sulfides [J].

Bates, CG ;

Saejueng, P ;

Doherty, MQ ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (26) :5005-5008

[9] A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].

Bates, CG ;

Gujadhur, RK ;

Venkataraman, D .

ORGANIC LETTERS, 2002, 4 (16) :2803-2806

[10] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

← 1 2 3 4 5 6 7 8 9 10 →