Biaryl thioether synthesis via CuI catalyzed dominothiolation of aryl halides in the presence of DMAP as ligand

被引：36

作者：

Roy, Subhasish ^{[1
]}

Phukan, Prodeep ^{[1
]}

机构：

[1] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 19期

关键词：

DMAP; CuI; C-S coupling; Aryl halide; Thiourea; CROSS-COUPLING REACTIONS; BARBIER-TYPE ALLYLATION; EFFICIENT LIGAND; N-ARYLATION; C-N; NUCLEOPHILIC-SUBSTITUTION; HIGHLY EFFICIENT; S BOND; COPPER; THIOLS;

D O I：

10.1016/j.tetlet.2015.03.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved protocol has been developed for the synthesis of symmetrical biaryl sulfides via a dominothiolation reaction using CuI as catalyst in the presence of DMAP as ligand. The coupling reaction of aryl halides was carried out in the presence of 5 mol % of CuI and 20 mol % of DMAP using thiourea as sulfur transfer agent. High yields of corresponding product were obtained by carrying out the reaction in DMSO at 120 degrees C. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2426 / 2429

页数：4

共 77 条

[1] Efficient syntheses of AZD4407 via thioether formation by nucleophilic attack of organometallic species on sulphur [J].

Alcaraz, ML ;

Atkinson, S ;

Cornwall, P ;

Foster, AC ;

Gill, DM ;

Humphries, LA ;

Keegan, PS ;

Kemp, R ;

Merifield, E ;

Nixon, RA ;

Noble, AJ ;

O'Beirne, D ;

Patel, ZM ;

Perkins, J ;

Rowan, P ;

Sadler, P ;

Singleton, JT ;

Tornos, J ;

Watts, AJ ;

Woodland, IA .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (05) :555-569

[2]

[Anonymous], 1985, NEW REPUBLIC, V193, P7

[3]

[Anonymous], 2014, ECONOMIST, V411, P30

[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] 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

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

Beletskaya, IP ;

Cheprakov, AV .

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

[7]

Berry D. J., 2001, ARKIVOC, Vi, P201

[8] Synthesis of Copper(I) Thiolate Complexes in the Thioetherification of Aryl Halides [J].

Chen, Chaohuang ;

Weng, Zhiqiang ;

Hartwig, John F. .

ORGANOMETALLICS, 2012, 31 (22) :8031-8036

[9] Synthesis of CuO on mesoporous silica and its applications for coupling reactions of thiols with aryl iodides [J].

Chen, Chin-Keng ;

Chen, Yan-Wun ;

Lin, Che-Hung ;

Lin, Hong-Ping ;

Lee, Chin-Fa .

CHEMICAL COMMUNICATIONS, 2010, 46 (02) :282-284

[10] 1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols [J].

Chen, Yao-Jung ;

Chen, Hsin-Hung .

ORGANIC LETTERS, 2006, 8 (24) :5609-5612

← 1 2 3 4 5 6 7 8 →