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Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides

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Listed:
  • Li-Li Zhang

    (Tongji University)

  • Yu-Zhong Gao

    (Shanxi Normal University)

  • Sheng-Han Cai

    (Tongji University)

  • Hui Yu

    (Tongji University)

  • Shou-Jie Shen

    (Shanxi Normal University)

  • Qian Ping

    (Tongji University)

  • Ze-Peng Yang

    (Tongji University)

Abstract

Transition metal-catalyzed enantioconvergent cross-coupling of an alkyl precursor presents a promising method for producing enantioenriched C(sp3) molecules. Because alkyl alcohol is a ubiquitous and abundant family of feedstock in nature, the direct reductive coupling of alkyl alcohol and aryl halide enables efficient access to valuable compounds. Although several strategies have been developed to overcome the high bond dissociation energy of the C − O bond, the asymmetric pattern remains unknown. In this report, we describe the realization of an enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohol (β-hydroxy ketone) and aryl bromide in the presence of an NHC activating agent. The approach can accommodate substituents of various sizes and functional groups, and its synthetic potency is demonstrated through a gram scale reaction and derivatizations into other compound families. Finally, we apply our convergent method to the efficient asymmetric synthesis of four β-aryl ketones that are natural products or bioactive compounds.

Suggested Citation

  • Li-Li Zhang & Yu-Zhong Gao & Sheng-Han Cai & Hui Yu & Shou-Jie Shen & Qian Ping & Ze-Peng Yang, 2024. "Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46713-x
    DOI: 10.1038/s41467-024-46713-x
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    References listed on IDEAS

    as
    1. Zhe Dong & David W. C. MacMillan, 2021. "Metallaphotoredox-enabled deoxygenative arylation of alcohols," Nature, Nature, vol. 598(7881), pages 451-456, October.
    2. Xiaokai Cheng & Huangzhe Lu & Zhan Lu, 2019. "Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
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