Task-specific ionic liquid as base, ligand and reaction medium for the palladium-catalyzed Heck reaction |
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| Authors: | Lei Wang Hongji Li |
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| Institution: | a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, PR China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China |
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| Abstract: | A novel ionic liquid, which was based on ethanolamine-functionalized quaternary ammonium salt was designed and synthesized. 4-Di(hydroxyethyl)aminobutyl tributylammonium bromide (DHEABTBAB) 1, a task-specific ionic liquid, which acts as a base, ligand and reaction medium, exhibits a very high activity and recyclability to palladium-catalyzed Heck reaction. The olefinations of iodoarenes, bromoarenes and chloroarenes with olefins generated the corresponding cross-coupling products in good to excellent yields only in the presence of DHEABTBAB and palladium acetate under phosphine-free reaction conditions. It is noteworthy that palladium and DHEABTBAB could be repeatedly recycled and reused for six consecutive trials without significant loss of their activities. |
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| Keywords: | Heck reaction Task-specific ionic liquid (TSIL) Ethanolamine-functionalized quaternary ammonium salt 4-Di(hydroxyethyl)aminobutyl tributylammonium bromide (DHEABTBAB) |
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