Carbon-Sulfur Bond Formation of Challenging Substrates at Low Temperature by Using Pd-PEPPSI-IPent

被引:127
作者
Sayah, Mahmoud [1 ]
Organ, Michael G. [1 ]
机构
[1] York Univ, Dept Chem, Toronto, ON M3J 1P3, Canada
关键词
cross-coupling; palladium; PEPPSI; sulfination; ORTHO-SUBSTITUTED BIARYLS; PALLADIUM-CATALYZED SYNTHESIS; ARYL CHLORIDES; S-ARYLATION; EFFICIENT; THIOLS; THIOETHERS; SULFIDES; BROMIDES; IODIDES;
D O I
10.1002/chem.201102158
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aryl thiols made cool and quick: The coupling of alkyl, aryl, and silyl thiols to hindered, deactivated aryl bromides and chlorides has been achieved under the most mild temperatures yet reported (i.e., room temperature to 40°C). The bulk afforded by the di-2,6-(3-propylphenyl)imidazolium-derived Pd-PEPPSI-IPent catalyst is believed to actively promote the critical reductive elimination step of the catalytic cycle, thereby eliminating the formation of poisonous off-cycle dimeric resting states that have plagued Pd-catalyzed sulfination reactions. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11719 / 11722
页数:4
相关论文
共 30 条
[1]   Microwave-Assisted Ullmann C-S Bond Formation: Synthesis of the P38α MAPK Clinical Candidate VX-745 [J].
Bagley, Mark C. ;
Davis, Terence ;
Dix, Matthew C. ;
Fusillo, Vincenzo ;
Pigeaux, Morgane ;
Rokicki, Michal J. ;
Kipling, David .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8336-8342
[2]   Rapid palladium-catalyzed cross-coupling in the synthesis of aryl thioethers under microwave conditions [J].
Cai, Lisheng ;
Cuevas, Jessica ;
Peng, Yi-Yuan ;
Pike, Victor W. .
TETRAHEDRON LETTERS, 2006, 47 (26) :4449-4452
[3]  
Calimsiz S., 2010, Angewandte Chemie, V122, P2058
[4]   Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent [J].
Calimsiz, Selcuk ;
Organ, Michael G. .
CHEMICAL COMMUNICATIONS, 2011, 47 (18) :5181-5183
[5]   Pd-PEPPSI-IPent: Low-Temperature Negishi Cross-Coupling for the Preparation of Highly Functionalized, Tetra-ortho-Substituted Biaryls [J].
Calimsiz, Selcuk ;
Sayah, Mahmoud ;
Mallik, Debasis ;
Organ, Michael G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (11) :2014-2017
[6]   Simple and efficient recyclable catalytic system for performing copper-catalysed S-arylation reactions in the presence of water [J].
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther ;
Tellitu, Imanol .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) :5100-5105
[7]   A NEW, PALLADIUM-CATALYZED SYNTHESIS OF AROMATIC MERCAPTURIC ACID-DERIVATIVES [J].
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1995, 36 (23) :4133-4136
[8]  
Correa A., 2008, ANGEW CHEM, V120, P2922, DOI DOI 10.1002/ANGE.200705668
[9]   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
[10]   New arylthioindoles: Potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies [J].
De Martino, G ;
Edler, MC ;
La Regina, G ;
Coluccia, A ;
Barbera, MC ;
Barrow, D ;
Nicholson, RI ;
Chiosis, G ;
Brancale, A ;
Hamel, E ;
Artico, M ;
Silvestri, R .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (03) :947-954