A general and efficient CuI/BtH catalyzed coupling of aryl halides with thiols

被引:149
作者
Verma, Akhilesh Kumar [1 ]
Singh, Jaspal [1 ]
Chaudhary, Ritu [1 ]
机构
[1] Univ Delhi, Dr BR Ambedkar Ctr Biomed Res, Synthet Organ Chem Res Lab, Delhi 110007, India
关键词
benzotriazole; Cul; aryl sulfide; C-S coupling; aryl bromides;
D O I
10.1016/j.tetlet.2007.07.205
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report an exceptionally mild, general and efficient copper catalyzed cross coupling reaction of aryl bromides and thiols using 0.5 mol % CuI and 1 mol % benzotriazole. Experimental simplicity, generality, functional group tolerance and low cost of the catalyst are advantages of the protocol. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7199 / 7202
页数:4
相关论文
共 47 条
[1]   One-Pot two-step synthesis of aryl sulfur compounds by photoinduced reactions of thiourea anion with aryl halides [J].
Arguello, JE ;
Schmidt, LC ;
Peñéñory, AB .
ORGANIC LETTERS, 2003, 5 (22) :4133-4136
[2]   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
[3]   A NEW SYNTHESIS OF FPL-64176 AND ANALOGS - THE DISCOVERY OF BENZOYLPYRROLE CALCIUM-CHANNEL ACTIVATORS WITH LOW NANOMOLAR POTENCY [J].
BAXTER, AJG ;
TEAGUE, SJ .
TETRAHEDRON, 1993, 49 (40) :9089-9094
[4]   A NEW, PALLADIUM-CATALYZED SYNTHESIS OF AROMATIC MERCAPTURIC ACID-DERIVATIVES [J].
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1995, 36 (23) :4133-4136
[5]   Preparation and resolution of 2,2′-dimercapto-6,6′-dimethoxy-1,1′-biphenyl:: a C2-symmetric sulfur building block [J].
Delogu, G ;
Fabbri, D ;
Dettori, MA .
TETRAHEDRON-ASYMMETRY, 1998, 9 (16) :2819-2826
[6]   CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands [J].
Deng, W ;
Zou, Y ;
Wang, YF ;
Liu, L ;
Guo, QX .
SYNLETT, 2004, (07) :1254-1258
[7]   A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols [J].
Fernández-Rodríguez, MA ;
Shen, QL ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2180-2181
[8]   A facile one-pot synthesis of alkyl aryl sulfides from aryl bromides [J].
Ham, JY ;
Yang, IH ;
Kang, HJ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3236-3239
[9]  
Harr MS, 1999, SYNLETT, P1579
[10]   SYNTHESIS OF AROMATIC S-SUBSTITUTED DERIVATIVES OF N-ACETYL-L-CYSTEINE [J].
HICKMAN, RJS ;
CHRISTIE, BJ ;
GUY, RW ;
WHITE, TJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (06) :899-904