Ligand-Free-Palladium-Catalyzed Direct 4-Arylation of Isoxazoles Using Aryl Bromides

被引:78
作者
Fall, Yacoub [2 ]
Reynaud, Celine [2 ]
Doucet, Henri [1 ]
Santelli, Maurice [2 ]
机构
[1] Univ Rennes, CNRS, UMR 6226, Inst Sci Chim Rennes, F-35042 Rennes, France
[2] CNRS, Fac Sci St Jerome, Synth Organ Lab, F-75700 Paris, France
关键词
Atom-economy; Homogeneous catalysis; C-H activation; Heteroaryl halides; Isoxazole; Palladium; CROSS-COUPLING REACTION; C-H FUNCTIONALIZATION; DIRECT C-2 ARYLATION; CONVENIENT SYNTHESIS; BORONIC ESTERS; DERIVATIVES; CHLORIDES; LOADINGS; 1,2,3-TRIAZOLES; THIAZOLES;
D O I
10.1002/ejoc.200900309
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Arylisoxazoles can be easily prepared by a palladium-catalysed C-H bond activation/arylation of 3,5-disubstituted isoxazoles using aryl or heteroaryl bromides. Good yields were generally obtained by using 0.1-0.5 mol-% of the airstable PdCl2 complex as the catalyst. A range of functional groups such as acetyl, formyl, ester, fluoro, nitro, trifluoromethyl or nitrile on the aryl bromide is tolerated. This reaction is environmentally attractive, as the major waste is KBr/AcOH instead of the metallic salts arising from classical cross-coupling procedures. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码:4041 / 4050
页数:10
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