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Pd(NHC)(cinnamyl)Cl-catalyzed Suzuki cross-coupling reaction of aryl sulfonates with arylboronic acids

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Abstract

A series of N-heterocyclic carbene (NHC)–palladium catalysts have been synthesized and applied to catalyze the Suzuki coupling reaction efficiently between aryl sulfonates and arylboronic acids with the potassium phosphate heptahydrate as a base. The desired yields are obtained even with less reactive aryl tosylates or aryl mesylates as substrates. This method was applied successfully to the synthesis of the (R)-2-(t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propan-1-ol which is the key intermediate of sacubitril, a component of the newly approved antihypertensive drug “Entresto.”

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Acknowledgements

We gratefully acknowledge the Science and Technology Department of Sichuan Province (2019JDJQ0010). We would also like to thank Dr. Jinkun Huang for helpful comments.

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Authors and Affiliations

  1. Department of Chemistry, Xihua University, Chengdu, 610039, China

    Qiwei Wang

  2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China

    Qiwei Wang, Zhen Dai, Xiangjie Di, QingFei Huang & Jin Zhu

  3. Graduate University of Chinese Academy of Sciences, Beijing, 100049, China

    Zhen Dai & Xiangjie Di

  4. College of Chemistry, Sichuan University, Chengdu, 610065, China

    Yuanhua Wang

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  1. Qiwei Wang
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Correspondence to Qiwei Wang, QingFei Huang or Yuanhua Wang.

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Wang, Q., Dai, Z., Di, X. et al. Pd(NHC)(cinnamyl)Cl-catalyzed Suzuki cross-coupling reaction of aryl sulfonates with arylboronic acids. Mol Divers 24, 903–911 (2020). https://doi.org/10.1007/s11030-019-10001-4

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