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Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay

Author

Listed:
  • Xian Zhao

    (Donghua University)

  • Hai-Yong Tu

    (Donghua University)

  • Lei Guo

    (Donghua University)

  • Shengqing Zhu

    (Donghua University)

  • Feng-Ling Qing

    (Donghua University
    Chinese Academy of Science)

  • Lingling Chu

    (Donghua University)

Abstract

The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging. To date, the vast majority of alkene carboacylation reactions are typically restricted to single- and two-component methodologies. Here we describe a three-component carboacylation of alkenes via the merger of radical chemistry with nickel catalysis. This reaction manifold utilizes a radical relay strategy involving radical addition to an alkene followed by alkyl radical capture by an acyl-nickel complex to forge two vicinal C−C bonds under mild conditions. Excellent chemoselectivity and regioselectivity have been achieved by utilizing a pendant weakly chelating group. This versatile protocol allows for facile access to a wide range of important β-fluoroalkyl ketones from simple starting materials.

Suggested Citation

  • Xian Zhao & Hai-Yong Tu & Lei Guo & Shengqing Zhu & Feng-Ling Qing & Lingling Chu, 2018. "Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-05951-6
    DOI: 10.1038/s41467-018-05951-6
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    Cited by:

    1. You-Feng Han & Ying Huang & Hao Liu & Zhong-Hua Gao & Chun-Lin Zhang & Song Ye, 2022. "Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    2. Shanglin Chen & Ya-Nan Wang & Jinhui Xie & Wangyang Li & Mingxing Ye & Xingxing Ma & Kai Yang & Shijun Li & Yu Lan & Qiuling Song, 2024. "Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions," Nature Communications, Nature, vol. 15(1), pages 1-14, December.
    3. Hai-Ying Wang & Xin-Han Wang & Bang-An Zhou & Chun-Lin Zhang & Song Ye, 2023. "Ketones from aldehydes via alkyl C(sp3)−H functionalization under photoredox cooperative NHC/palladium catalysis," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    4. Jinwei Sun & Yongze Zhou & Rui Gu & Xin Li & Ao Liu & Xuan Zhang, 2022. "Regioselective Ni-Catalyzed reductive alkylsilylation of acrylonitrile with unactivated alkyl bromides and chlorosilanes," Nature Communications, Nature, vol. 13(1), pages 1-10, December.

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