Ligand-Free Palladium-Catalyzed Direct Arylation of Thiazoles at Low Catalyst Loadings

被引:113
作者
Roger, Julien [1 ]
Pozgan, Franc [1 ]
Doucet, Henri [1 ]
机构
[1] Univ Rennes Catalyse & Organomet, CNRS, UMR 6226, Inst Sci Chim Rennes, F-35042 Rennes, France
关键词
USEFUL COUPLING PARTNERS; C-H FUNCTIONALIZATION; ARYL CHLORIDES; HECK REACTIONS; BOND FORMATION; PLASMEPSIN-I; HETEROAROMATICS; ACTIVATION; HALIDES; ACCESS;
D O I
10.1021/jo802360d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ligand-free Pd(OAc)(2) was found to catalyze very efficiently the direct arylation of thiazole derivatives under very low catalyst concentration. By using activated aryl bromides, the reaction can be performed employing as little as 0.1-0.001 mol % catalyst. With such substrates, this procedure is economically and environmentally attractive. On the other hand, in the presence of more challenging substrates, such as some strongly deactivated or highly congested aryl bromides, in some cases, disappointing results were obtained.
引用
收藏
页码:1179 / 1186
页数:8
相关论文
共 43 条
[1]   Palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides using conventional heating [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Born, Robert .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) :741-748
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]   Use of "homeopathic" ligand-free palladium as catalyst for aryl-aryl coupling reactions [J].
Alimardanov, A ;
de Vondervoort, LSV ;
de Vries, AHM ;
de Vries, JG .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1812-1817
[4]  
AOYAGI Y, 1992, HETEROCYCLES, V33, P257
[5]   Direct arylation of Thiophenes via palladium-catalysed C-H functionalisation at low catalyst loadings [J].
Battace, Ahmed ;
Lemhadri, Mhamed ;
Zair, Touriya ;
Doucet, Henri ;
Santelli, Maurice .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (16) :2507-2516
[6]   Palladium-catalyzed direct arylation of furans via C-H functionalization at low catalyst loadings [J].
Battace, Ahmed ;
Lemhadri, Mhamed ;
Zair, Touriya ;
Doucet, Henri ;
Santelli, Maurice .
ORGANOMETALLICS, 2007, 26 (03) :472-474
[7]   Ligandless microwave-assisted Pd/Cu-catalyzed direct arylation of oxazoles [J].
Besselievre, Francois ;
Mahuteau-Betzer, Florence ;
Grierson, David S. ;
Piguel, Sandrine .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3278-3280
[8]   C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions [J].
Campeau, Louis-Charles ;
Bertrand-Laperle, Megan ;
Leclerc, Jean-Philippe ;
Villemure, Elisia ;
Gorelsky, Serge ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3276-+
[9]  
Campeau LC, 2007, ALDRICHIM ACTA, V40, P35
[10]   Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides [J].
Chiong, Hendrich A. ;
Daugulis, Olafs .
ORGANIC LETTERS, 2007, 9 (08) :1449-1451