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

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Abstract

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, mPEG16MeImI, and K2CO3 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 6 h. After extraction of the product, the catalyst containing mPEG n MeImI phase could be recycled for five times without significant loss of activity.

Graphical Abstract

Three PEG-modified NHC ligands with different PEG chain lengths (mPEGnMeImI, 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, mPEG16MeImI, and K2CO3 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 6 h. 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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Acknowledgments

Financial support for this work was provided by the National Natural Science Foundation of China (Nos. 21241005 and 21201040), the Key Laboratory of Jiangxi University for Functional Materials Chemistry.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, 341000, People’s Republic of China

    Jun Xue, Zhonggao Zhou, Jie Peng, Fan Du, Lifang Xie, Guohai Xu, Guiping Huang & Yongrong Xie

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  1. Jun Xue
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  2. Zhonggao Zhou
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  3. Jie Peng
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  4. Fan Du
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  5. Lifang Xie
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  7. Guiping Huang
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  8. Yongrong Xie
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Correspondence to Zhonggao Zhou or Yongrong Xie.

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Xue, J., Zhou, Z., Peng, J. et al. PEG-functionalized NHC ligands for efficient and recyclable palladium-catalyzed Suzuki reactions in water. Transition Met Chem 39, 221–224 (2014). https://doi.org/10.1007/s11243-013-9793-6

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