Functionalized Ionic Liquid as an Efficient and Recyclable Reaction Medium for Phosphine-Free Palladium-Catalyzed Heck Reaction

Li Zhou; Lei Wang

doi:10.1055/s-2006-942466

PAPER

Functionalized Ionic Liquid as an Efficient and Recyclable Reaction Medium for Phosphine-Free Palladium-Catalyzed Heck Reaction

Li Zhou^a, Lei Wang*^a,b
^a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;

Abstract

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Abstract

A functionalized ionic liquid, 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate ([HEmim][BF₄]), was found to be as an efficient and recyclable reaction medium for palladium-catalyzed Heck reaction. The olefination of iodoarenes and bromoarenes with olefins generated the corresponding products in good to excellent yields under phosphine-free reaction conditions. The reaction involved the use of [HEmim][BF₄] as the solvent, potassium phosphate as the base, and palladium acetate as the catalyst. In addition, palladium and ionic liquid could be recovered and recycled for six consecutive trials without significant loss of its reactivity.

Key words

Heck reaction - palladium acetate - phosphine-free - functionalized ionic liquid - 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate ([HEmim][BF₄])

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