Heterogeneous Suzuki and copper-free Sonogashira cross-coupling reactions catalyzed by a reusable palladium(II) complex in water medium

被引:114
作者
Islam, S. M. [1 ]
Mondal, Paramita [1 ]
Roy, Anupam Singha [1 ]
Mondal, Sanchita [1 ]
Hossain, Dilder [1 ]
机构
[1] Kalyani Univ, Dept Chem, Nadia 741235, W Bengal, India
关键词
Suzuki reaction; Sonogashira reaction; Water medium; Polystyrene anchored Pd(II) azo complex; PCP-PINCER COMPLEXES; SUPPORTED PALLADIUM(0); PALLADACYCLE CATALYST; AEROBIC CONDITIONS; TRANSITION-METALS; AQUEOUS-MEDIA; HECK; SILICA; CARBON; DERIVATIVES;
D O I
10.1016/j.tetlet.2010.02.079
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new polystyrene anchored Pd(II) azo complex has been synthesized and characterized. The present Pd(II) azo complex behaves as a very efficient heterogeneous catalyst in the Suzuki coupling and Sonogashira coupling reaction in water medium. Aryl halides, coupled with phenylboronic acids (Suzuki-Miyaura reaction) or terminal alkyne (Sonogashira reaction), smoothly afford the corresponding cross-coupling products in excellent yields (83-100% yield for Suzuki reaction and 68-96% yield for Sonogashira reaction of aryl halides) under phosphine-free reaction conditions in the presence of polystyrene anchored Pd(II) azo complex catalyst in water medium. Furthermore, the catalyst has shown good thermal stability and recyclability. This polymer-supported Pd(II) catalyst could be easily recovered by simple filtration of the reaction mixture and reused for more than six consecutive trials without a significant loss of its catalytic activity. (C) 2010 Elsevier Ltd. All rights reserved.
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页码:2067 / 2070
页数:4
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