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Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent

Author

Listed:
  • Mingrui Li

    (Northeast Normal University)

  • Yingtao Wu

    (Northeast Normal University)

  • Xiao Song

    (Northeast Normal University)

  • Jiaqiong Sun

    (Northeast Normal University
    Northeast Normal University)

  • Zuxiao Zhang

    (University of Hawai’i at Mānoa. 2545 McCarthy Mall)

  • Guangfan Zheng

    (Northeast Normal University)

  • Qian Zhang

    (Northeast Normal University
    Chinese Academy of Sciences 345 Lingling Lu)

Abstract

The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis of nitrogen-containing compounds. However, bifunctional C–N reagents have never been employed in the carboamination of cyclopropane. In this study, we use an N-heterocyclic carbene (NHC), N-benzoyl saccharin, as a bifunctional reagent and a photoredox catalyst for a dual-catalyzed 1,3-aminoacylation of cyclopropane. NHCs play multiple roles, functioning as Lewis base catalysts to activate C–N bonds, promoting the oxidative quenching process of PC*, and acting as efficient acyl radical transfer catalysts for the formation of C–C bonds. The oxidative quenching process between the excited-state PC* and acyl NHC adduct is the key to the photooxidation generality of aryl cyclopropanes.

Suggested Citation

  • Mingrui Li & Yingtao Wu & Xiao Song & Jiaqiong Sun & Zuxiao Zhang & Guangfan Zheng & Qian Zhang, 2024. "Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-53202-8
    DOI: 10.1038/s41467-024-53202-8
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    References listed on IDEAS

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