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Synthesis of benzoheterocycles by palladium-catalyzed migratory cyclization through an unexpected reaction cascade

Author

Listed:
  • Wen-Cong Li

    (Inner Mongolia University
    Chongqing University
    Chengdu University
    Inner Mongolia Academy of Science and Technology)

  • Lin Zhang

    (Chongqing University)

  • Shiming Bai

    (Inner Mongolia Academy of Science and Technology)

  • Jia-Hao Zhao

    (Inner Mongolia University
    Chengdu University)

  • Guang-Rui Liu

    (Inner Mongolia University
    Chengdu University)

  • Yu Lan

    (Chongqing University
    Henan Normal University)

  • Shufeng Chen

    (Inner Mongolia University)

  • Jialin Ming

    (Inner Mongolia University
    Chengdu University)

Abstract

Migratory functionalization of C–H bonds through metal migration from carbon to carbon under transition metal catalysis is a process of significant academic and industrial interest. Herein, a palladium-catalyzed migratory cyclization of α-bromoalkene derivatives ArXCBr=CH2, in which X denotes a phosphorus (P(O)R), silicon (SiR2), sulfur (SO2), carbon (C(O)), nitrogen (NTs), or oxygen-based moiety, affording various benzoheterocyclic compounds has been developed. Mechanistic investigations have demonstrated that the cyclization reaction proceeds through an unexpected cascade, with trans-1,2-palladium migration between sp2 carbons being a key step of catalytic cycle. To the best of our knowledge, this type of metal migration has not been reported previously.

Suggested Citation

  • Wen-Cong Li & Lin Zhang & Shiming Bai & Jia-Hao Zhao & Guang-Rui Liu & Yu Lan & Shufeng Chen & Jialin Ming, 2025. "Synthesis of benzoheterocycles by palladium-catalyzed migratory cyclization through an unexpected reaction cascade," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-58633-5
    DOI: 10.1038/s41467-025-58633-5
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