A general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphines

被引:408
作者
Murata, M [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
palladium catalysis; thiol cross-coupling; phosphine cross-coupling;
D O I
10.1016/j.tet.2004.05.044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The general and efficient cross-coupling of thiols with aryl halides was developed utilizing Pd(OAC)(2)/1,1'-bis(diisopropylphosphino)ferrocene as the catalyst. The substrate scope is broad and includes a variety of aryl bromides and chlorides, which can be coupled to aliphatic and aromatic thiols. This catalyst system has the widest substrate scope of any reported to date. The present catalyst system also enables the palladium-catalyzed coupling of secondary phosphines with aryl bromides and chlorides. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7397 / 7403
页数:7
相关论文
共 45 条
[21]   Highly active, air-stable palladium catalysts for the C-C and C-S bond-forming reactions of vinyl and aryl chlorides:: Use of commercially available [(t-Bu)2P(OH)]2PdCl2, [(t-Bu)2P(OH)PdCl2]2, and [[(t-Bu)2PO•••H•••OP(t-Bu)2]PdCl]2 as catalysts [J].
Li, GY .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3643-3650
[22]   Highly active, air-stable versatile palladium catalysts for the C-C, C-N, and C-S bond formations via cross-coupling reactions of aryl chlorides [J].
Li, GY ;
Zheng, G ;
Noonan, AF .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8677-8681
[23]  
Li GY, 2001, ANGEW CHEM INT EDIT, V40, P1513, DOI 10.1002/1521-3773(20010417)40:8<1513::AID-ANIE1513>3.0.CO
[24]  
2-C
[25]   Pd(O)-mediated couplings of aryl nonaflates and triflates with diphenylphosphine-borane.: Preparation of BH3-stabilized, unsymmetrical triarylphosphines [J].
Lipshutz, BH ;
Buzard, DJ ;
Yun, CS .
TETRAHEDRON LETTERS, 1999, 40 (02) :201-204
[26]  
Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
[27]  
2-U
[28]   Carbon-sulfur bond-forming reductive elimination involving sp-, sp2-, and sp3-hybridized carbon.: Mechanism, steric effects, and electronic effects on sulfide formation [J].
Mann, G ;
Baranano, D ;
Hartwig, JF ;
Rheingold, AL ;
Guzei, IA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9205-9219
[29]   Direct palladium-catalyzed phosphinylation of aryl triflates with secondary phosphines.: Its scope and limitations:: The synthesis of optically active carboxylated 2-(diphenylphosphino)-1,1′-binaphthalenes [J].
Martorell, G ;
Garcías, X ;
Janura, M ;
Saá, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3463-3467
[30]  
McWilliams J. C., 2002, ORG SYNTH, V79