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Photo-induced catalytic halopyridylation of alkenes

Author

Listed:
  • Shi-Yu Guo

    (Chinese Academy of Sciences)

  • Fan Yang

    (Chinese Academy of Sciences)

  • Ting-Ting Song

    (Chinese Academy of Sciences)

  • Yu-Qing Guan

    (Chinese Academy of Sciences)

  • Xiang-Ting Min

    (Chinese Academy of Sciences)

  • Ding-Wei Ji

    (Chinese Academy of Sciences)

  • Yan-Cheng Hu

    (Chinese Academy of Sciences)

  • Qing-An Chen

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

The Mizoroki-Heck reaction and its reductive analogue are staples of organic synthesis, but the ensuing products often lack a chemical handle for further transformation. Here we report an atom-economical cross-coupling of halopyridines and unactivated alkenes under photoredox catalysis to afford a series of alkene halopyridylation products. This protocol with mild and redox neutral conditions contributes broad substrate scope. As a complement to conventional Heck-type reaction, this radical process avoids the involvement of β-H elimination and thus useful pyridyl and halide groups could be simultaneously and regioselectively incorporated onto alkenes. The success depends on TFA-promoted domino photocatalytic oxidative quenching activation and radical-polar crossover pathway. Plausible mechanism is proposed based on mechanistic investigations. Moreover, the reserved C − X bonds of these products are beneficial for performing further synthetic elaborations.

Suggested Citation

  • Shi-Yu Guo & Fan Yang & Ting-Ting Song & Yu-Qing Guan & Xiang-Ting Min & Ding-Wei Ji & Yan-Cheng Hu & Qing-An Chen, 2021. "Photo-induced catalytic halopyridylation of alkenes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
  • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-26857-w
    DOI: 10.1038/s41467-021-26857-w
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    Cited by:

    1. Shi-Yu Guo & Yi-Peng Liu & Jin-Song Huang & Li-Bowen He & Gu-Cheng He & Ding-Wei Ji & Boshun Wan & Qing-An Chen, 2024. "Visible light-induced chemoselective 1,2-diheteroarylation of alkenes," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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