PEG-functionalized NHC ligands for efficient and recyclable palladium-catalyzed Suzuki reactions in water

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作者：

J Xue，Z Zhou，J Peng，F Du，L Xie，G Xu，G Huang，Y Xie

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摘要：

We have used poly(ethylene glycol)-functionalized N-heterocyclic carbene ligands, 1-(methoxy PEG)-3-methylimidazolium iodides together with Pd(OAc) 2 as efficient catalysts for the Suzuki reaction in water. The best catalytic system generated in situ from Pd(OAc) 2 , mPEG 16 MeImI, and K 2 CO 3 is able to mediate the Suzuki coupling of a series of aryl boronic acids and aryl halides, except for deactivated aryl chlorides, in good to almost quantitative yields in water within 6h. After extraction of the product, the catalyst containing mPEG n MeImI phase could be recycled for five times without significant loss of activity. GraphicalThree PEG-modified NHC ligands with different PEG chain lengths (mPEG n MeImI, n =7, 12, and 16) were used for Pd-catalyzed Suzuki reactions in water. The best catalytic system generated in situ from Pd(OAc) 2 , mPEG 16 MeImI, and K 2 CO 3 is able to mediate the Suzuki coupling of a series of aryl boronic acids and aryl halides, except for deactivated aryl chlorides, in good to almost quantitative yields in water within 6h. After extraction of the product, the catalyst containing mPEG n MeImI phase could be recycled for five times without significant loss of activity.

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关键词：

Boronic Acid Aryl Halide Phenylboronic Acid Suzuki Reaction Suzuki Coupling

DOI：

10.1007/s11243-013-9793-6

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年份：

2014