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Aryl radical-mediated N-heterocyclic carbene catalysis

Author

Listed:
  • Yuki Matsuki

    (Kanazawa University, Kakuma-machi)

  • Nagisa Ohnishi

    (Kanazawa University, Kakuma-machi)

  • Yuki Kakeno

    (Kanazawa University, Kakuma-machi)

  • Shunsuke Takemoto

    (Kanazawa University, Kakuma-machi)

  • Takuya Ishii

    (Kanazawa University, Kakuma-machi)

  • Kazunori Nagao

    (Kanazawa University, Kakuma-machi)

  • Hirohisa Ohmiya

    (Kanazawa University, Kakuma-machi
    JST, PRESTO)

Abstract

There have been significant advancements in radical reactions using organocatalysts in modern organic synthesis. Recently, NHC-catalyzed radical reactions initiated by single electron transfer processes have been actively studied. However, the reported examples have been limited to catalysis mediated by alkyl radicals. In this article, the NHC organocatalysis mediated by aryl radicals has been achieved. The enolate form of the Breslow intermediate derived from an aldehyde and thiazolium-type NHC in the presence of a base undergoes single electron transfer to an aryl iodide, providing an aryl radical. The catalytically generated aryl radical could be exploited as an arylating reagent for radical relay-type arylacylation of styrenes and as a hydrogen atom abstraction reagent for α-amino C(sp3)–H acylation of secondary amides.

Suggested Citation

  • Yuki Matsuki & Nagisa Ohnishi & Yuki Kakeno & Shunsuke Takemoto & Takuya Ishii & Kazunori Nagao & Hirohisa Ohmiya, 2021. "Aryl radical-mediated N-heterocyclic carbene catalysis," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-24144-2
    DOI: 10.1038/s41467-021-24144-2
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    Cited by:

    1. 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.
    2. Hangyeol Choi & Gangadhar Rao Mathi & Seonghyeok Hong & Sungwoo Hong, 2022. "Enantioselective functionalization at the C4 position of pyridinium salts through NHC catalysis," Nature Communications, Nature, vol. 13(1), pages 1-8, December.

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