An efficient method for the N-arylation of phenylurea via copper catalyzed amidation

被引：15

作者：

Gavade, Sandip N. ^{[1
]}

Balaskar, Ravi S. ^{[1
]}

Mane, Madhav S. ^{[1
]}

Pabrekar, Prarnod N. ^{[3
]}

Shingare, Murlidhar S. ^{[2
]}

Mane, Dhananjay V. ^{[1
]}

机构：

[1] SCS Coll, Organ Res Lab, Omerga 413606, MS, India

[2] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem, Aurangabad 431004, Maharashtra, India

[3] VG Vaze Coll, Bombay 400081, Maharashtra, India

来源：

CHINESE CHEMICAL LETTERS | 2011年 / 22卷 / 06期

关键词：

Copper catalyst; Urea; Aryl halides; Amidation; BOND FORMATION; ARYL BROMIDES; UREAS; DERIVATIVES; AMINATION; MECHANISM; IODIDES; HALIDES; ETHERS; SCOPE;

D O I：

10.1016/j.cclet.2010.12.018

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The coupling reaction of phenylurea with different functionalized aryl halides in the presence of air stable Cut, N,N-dimethylethylenediamine as a ligand, and K3PO4 as a base gives symmetrical and unsymmetrical diarylureas in relatively high yields. This method is milder than the palladium catalyzed arylation and avoids the use of toxic phosphine ligands. (C) 2010 Dhananjay V. Mane. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

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收藏

页码：675 / 678

页数：4

相关论文

共 24 条

[1] ELIMINATION-ADDITION MECHANISM FOR BASE-CATALYZED CONVERSION OF S-ALKYLISOTHIOUREAS TO UREAS [J].

BRIODY, TA ;

HEGARTY, AF ;

SCOTT, FL .

TETRAHEDRON, 1977, 33 (12) :1469-1474

[2]

Davis T.L., 1929, J. Am. Chem. Soc, V51, P1790

[3] SYNTHESIS OF 1,2,3,5-OXATHIADIAZOLE 2-OXIDES FROM AMIDOXIMES AND THIONYL CHLORIDE AND MECHANISM OF THEIR THERMALLY INDUCED FRAGMENTATION AND REARRANGEMENT TO CARBODIIMIDES [J].

DONDONI, A ;

BARBARO, G ;

BATTAGLIA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (21) :3372-3377

[4] HYDROGEN-BOND DIRECTED COCRYSTALLIZATION AND MOLECULAR RECOGNITION PROPERTIES OF DIARYLUREAS [J].

ETTER, MC ;

URBANCZYKLIPKOWSKA, Z ;

ZIAEBRAHIMI, M ;

PANUNTO, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8415-8426

[5] Concerning phenylization in the presence of copper as a catalytic agent. [J].

Goldberg, I .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1906, 39 :1691-1692

[6] Synthesis of diaryl ethers using an easy-to-prepare, air-stable, soluble copper(I) catalyst [J].

Gujadhur, R ;

Venkataraman, D .

SYNTHETIC COMMUNICATIONS, 2001, 31 (18) :2865-2879

[7] Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].

Hartwig, JF ;

Kawatsura, M ;

Hauck, SI ;

Shaughnessy, KH ;

Alcazar-Roman, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580

[8] Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides [J].

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) :852-860

[9] SYNTHESIS OF OLIGO(M-ANILINE) [J].

ITO, A ;

SAITO, T ;

TANAKA, K ;

YAMABE, T .

TETRAHEDRON LETTERS, 1995, 36 (48) :8809-8812

[10] 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