Cu Nanoparticles in PEG: A New Recyclable Catalytic System for N-Arylation of Amines with Aryl Halides

被引：54

作者：

Kidwai, Mazaahir ^{[1
]}

Mishra, Neeraj Kumar ^{[1
]}

Bhardwaj, Saurav ^{[1
]}

Jahan, Anwar ^{[1
]}

Kumar, Ajeet ^{[2
]}

Mozumdar, Subho ^{[2
]}

机构：

[1] Univ Delhi, Dept Chem, Green Chem Res Lab, Delhi 110007, India

[2] Univ Delhi, Dept Chem, Lab Nanobiotechnol, Delhi 110007, India

来源：

CHEMCATCHEM | 2010年 / 2卷 / 10期

关键词：

amines; copper; cross-couplings; heterogeneous catalysis; nanoparticles; CROSS-COUPLING REACTIONS; PALLADIUM NANOPARTICLES; METAL NANOPARTICLES; ARYLBORONIC ACIDS; CUPRIC ACETATE; HECK REACTIONS; EFFICIENT; SUZUKI; CLUSTERS; BEHAVIOR;

D O I：

10.1002/cctc.201000062

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：

A new protocol for the N-arylation of aryl halides with anilines using Cu nanoparticles in polyethylene glycol (PEG) as an efficient and reusable catalytic system has been developed. The reaction did not require any cocatalyst. Various solvents were screened, and PEG(400) provided the best results. The studies showed that the mechanism of catalytic action is dependent on the size of the nanoparticles. The Cu nanoparticles and PEG were recyclable and retained their activity. This newly developed protocol was also found to be suitable for the cross coupling of N-H heterocycles with iodobenzene. The present methodology offers several advantages, such as excellent yields, short reaction times, and milder reaction conditions.

引用

页码：1312 / 1317

页数：6

共 41 条

[1] 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

[2] Polyethylene glycol and solutions of polyethylene glycol as green reaction media [J].

Chen, J ;

Spear, SK ;

Huddleston, JG ;

Rogers, RD .

GREEN CHEMISTRY, 2005, 7 (02) :64-82

[3] Transition-metal nanoparticles in imidazolium ionic liquids: Recycable catalysts for biphasic hydrogenation reactions [J].

Dupont, J ;

Fonseca, GS ;

Umpierre, AP ;

Fichtner, PFP ;

Teixeira, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4228-4229

[4] Cu-Based Nanoalloys in the Base-Free Ullmann Heterocyle-Aryl Ether Synthesis [J].

Engels, Volker ;

Benaskar, Faysal ;

Patil, Narendra ;

Rebrov, Evgeny V. ;

Hessel, Volker ;

Hulshof, Lumbertus A. ;

Jefferson, David A. ;

Vekemans, Jef A. J. M. ;

Karwal, Saurabh ;

Schouten, Jaap C. ;

Wheatley, Andrew E. H. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (03) :644-649

[5] 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

[6] CARDIOTONIC AGENTS - SYNTHESIS AND CARDIOVASCULAR PROPERTIES OF NOVEL 2-ARYLBENZIMIDAZOLES AND AZABENZIMIDAZOLES [J].

GUNGOR, T ;

FOUQUET, A ;

TEULON, JM ;

PROVOST, D ;

CAZES, M ;

CLOAREC, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (23) :4455-4463

[7]

Hartwig J.F., 1998, ANGEW CHEM INT EDIT, V110, P2154

[8]

Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO

[9]

2-L

[10] Aqueous two-phase systems - A general overview [J].

Hatti-Kaul, R .

MOLECULAR BIOTECHNOLOGY, 2001, 19 (03) :269-277

← 1 2 3 4 5 →