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Iodine-catalyzed diazo activation to access radical reactivity

Author

Listed:
  • Pan Li

    (Chinese Academy of Sciences
    University of South Florida)

  • Jingjing Zhao

    (Chinese Academy of Sciences)

  • Lijun Shi

    (Chinese Academy of Sciences)

  • Jin Wang

    (University of South Florida)

  • Xiaodong Shi

    (University of South Florida)

  • Fuwei Li

    (Chinese Academy of Sciences)

Abstract

Transition-metal-catalyzed diazo activation is a classical way to generate metal carbene, which are valuable intermediates in synthetic organic chemistry. An alternative iodine-catalyzed diazo activation is disclosed herein under either photo-initiated or thermal-initiated conditions, which represents an approach to enable carbene radical reactivity. This metal-free diazo activation strategy were successfully applied into olefin cyclopropanation and epoxidation, and applying this method to pyrrole synthesis under thermal-initiated conditions further demonstrates the unique reactivity using this method over typical metal-catalyzed conditions.

Suggested Citation

  • Pan Li & Jingjing Zhao & Lijun Shi & Jin Wang & Xiaodong Shi & Fuwei Li, 2018. "Iodine-catalyzed diazo activation to access radical reactivity," Nature Communications, Nature, vol. 9(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-04331-4
    DOI: 10.1038/s41467-018-04331-4
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