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Efficient PdCl2-catalyzed Suzuki reactions using simple dicationic imidazolium salts as ligands in aqueous DMF

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Abstract

Three new palladium catalysts, prepared via reactions of PdCl2 with readily obtained and inexpensive dicationic imidazolium salts, have been developed for the Suzuki reaction. The pre-catalyst was formed in situ using the imidazolium ligand, base and Pd metal precursor in 1,4-dioxane. This palladium catalyst provides a convenient and general method for the synthesis of biaryls from aryl bromides, activated aryl chlorides and arylboronic acids containing electron-withdrawing substituents and electron-donating groups (19 examples) in aqueous DMF under aerobic conditions (all 26 examples).

Graphical Abstract

Three new palladium catalysts made from PdCl2 and readily obtained inexpensive dicationic imidazolium salts have been developed for the Suzuki reaction. This palladium catalyst provides a convenient and general method to prepare biaryls from aryl bromides, activated aryl chlorides and arylboronic acids containing electron-withdrawing substituents and electron-donating groups (19 examples, all 26 examples) in aqueous DMF under air.

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Acknowledgments

We gratefully thank the financial support from 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

    Qing Huang, Jiabin Qiu, Limei Li, Guohai Xu & Zhonggao Zhou

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  1. Qing Huang
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  2. Jiabin Qiu
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  3. Limei Li
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  4. Guohai Xu
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  5. Zhonggao Zhou
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Corresponding author

Correspondence to Zhonggao Zhou.

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Huang, Q., Qiu, J., Li, L. et al. Efficient PdCl2-catalyzed Suzuki reactions using simple dicationic imidazolium salts as ligands in aqueous DMF. Transition Met Chem 39, 661–665 (2014). https://doi.org/10.1007/s11243-014-9847-4

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  • DOI: https://doi.org/10.1007/s11243-014-9847-4

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