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Catalytic enantioselective reductive domino alkyl arylation of acrylates via nickel/photoredox catalysis

Author

Listed:
  • Pengcheng Qian

    (Nanjing Tech University)

  • Haixing Guan

    (Nanjing Tech University
    Shandong University of Traditional Chinese Medicine)

  • Yan-En Wang

    (Hebei Agricultural University)

  • Qianqian Lu

    (Nanjing Tech University)

  • Fan Zhang

    (Nanjing Tech University)

  • Dan Xiong

    (Nanjing Tech University)

  • Patrick J. Walsh

    (University of Pennsylvania)

  • Jianyou Mao

    (Nanjing Tech University)

Abstract

Nonsteroidal anti-inflammatory drug derivatives (NSAIDs) are an important class of medications. Here we show a visible-light-promoted photoredox/nickel catalyzed approach to construct enantioenriched NSAIDs via a three-component alkyl arylation of acrylates. This reductive cross-electrophile coupling avoids preformed organometallic reagents and replaces stoichiometric metal reductants by an organic reductant (Hantzsch ester). A broad range of functional groups are well-tolerated under mild conditions with high enantioselectivities (up to 93% ee) and good yields (up to 90%). A study of the reaction mechanism, as well as literature precedence, enabled a working reaction mechanism to be presented. Key steps include a reduction of the alkyl bromide to the radical, Giese addition of the alkyl radical to the acrylate and capture of the α-carbonyl radical by the enantioenriched nickel catalyst. Reductive elimination from the proposed Ni(III) intermediate generates the product and forms Ni(I).

Suggested Citation

  • Pengcheng Qian & Haixing Guan & Yan-En Wang & Qianqian Lu & Fan Zhang & Dan Xiong & Patrick J. Walsh & Jianyou Mao, 2021. "Catalytic enantioselective reductive domino alkyl arylation of acrylates via nickel/photoredox catalysis," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-26794-8
    DOI: 10.1038/s41467-021-26794-8
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    Cited by:

    1. Long Zou & Xinyue Zheng & XueZheng Yi & Qingquan Lu, 2024. "Asymmetric paired oxidative and reductive catalysis enables enantioselective alkylarylation of olefins with C(sp3)−H bonds," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    2. Yuxi Gao & Lijuan Gao & Endiao Zhu & Yunhong Yang & Mi Jie & Jiaqian Zhang & Zhiqiang Pan & Chengfeng Xia, 2023. "Nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.

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