Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling

被引:69
作者
Guan, Pei [1 ,2 ]
Cao, Changsheng [1 ,2 ]
Liu, Yun [1 ,2 ]
Li, Yunfei [1 ,2 ]
He, Pan [1 ,2 ]
Chen, Qian [1 ,2 ]
Liu, Gang [1 ,2 ]
Shi, Yanhui [1 ,2 ,3 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China
[2] Jiangsu Normal Univ, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
[3] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
C-S bond formation; Cross-coupling; Thiols; Aryl halides; ARYL HALIDES; BOND FORMATION; THIOLS; LIGAND; COMPLEXES; SULFIDES; IODIDES; CARBON;
D O I
10.1016/j.tetlet.2012.08.055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cross-coupling reaction of aryl halides with aliphatic and aromatic thiols catalyzed by readily available Ni(OAc)(2) with N-heterocyclic carbene (NHC) is reported. Ni(OAc)(2)/NHC catalyst showed good activities toward various aryl halides in C-S coupling reaction, even with aryl chlorides. Reactions occurred in excellent yields, broad scope, and high tolerance of functional groups. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5987 / 5992
页数:6
相关论文
共 44 条
[1]   Recyclable Iron/Graphite Catalyst for C-S Cross Coupling of Thiols with Aryl Halides under Ligand-Free Conditions [J].
Akkilagunta, Vijay Kumar ;
Reddy, Vutukuri Prakash ;
Rao, Kakulapati Rama .
SYNLETT, 2010, (08) :1260-1264
[2]   Resting State and Elementary Steps of the Coupling of Aryl Halides with Thiols Catalyzed by Alkylbisphosphine Complexes of Palladium [J].
Alvaro, Elsa ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7858-7868
[3]  
[Anonymous], 1994, SULFUR REAGENTS ORGA
[4]   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
[5]   Rapid synthesis of VX-745: p38 MAP kinase inhibition in Werner syndrome cells [J].
Bagley, Mark C. ;
Davis, Terence ;
Dix, Matthew C. ;
Rokicki, Michal J. ;
Kipling, David .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (18) :5107-5110
[6]   Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic C-S Coupling [J].
Bryan, Christopher S. ;
Braunger, Julia A. ;
Lautens, Mark .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :7064-7068
[7]   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
[8]   Iron-catalyzed S-arylation of thiols with aryl iodides [J].
Correa, Arkaitz ;
Carril, Monica ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2880-2883
[9]   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
[10]   Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols [J].
Fernandez-Rodriguez, Manuel A. ;
Shen, Qilong ;
Hartwig, John F. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (30) :7782-7796