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Modular access to alkylfluorides via radical decarboxylative-desulfonylative gem-difunctionalization

Author

Listed:
  • Xianjin Wang

    (Shanghai Jiao Tong University)

  • Haotian Li

    (Soochow University)

  • Yasu Chen

    (Shanghai Jiao Tong University)

  • Ziqiang Wang

    (Shanghai Jiao Tong University
    Soochow University)

  • Xinxin Wu

    (Soochow University)

  • Chen Zhu

    (Shanghai Jiao Tong University
    Soochow University)

Abstract

Fluorine-containing compounds hold pivotal importance in life sciences. Recent decades have witnessed significant research efforts toward developing practical fluorination methods. Radical-mediated decarboxylative fluorination has proven to be a robust approach for incorporating diverse monofluoroalkyl groups. Here we show a radical-mediated modular synthesis of alkyl fluorides through a decarboxylative-desulfonylative gem-difunctionalization under mild photochemical conditions. The multi-component reaction proceeds in a controlled sequence of radical decarboxylation and heteroaryl migration, governed by radical polarity and kinetic effects, resulting in a wide range of valuable alkyl fluorides. Two C-C bonds and one C-F bond are concurrently formed throughout the process. Both styrenes and aliphatic alkenes serve as suitable substrates for this transformation. Furthermore, this method can be applied to the incorporation of a monofluoroalkyl moiety into complex alkene molecules at a late stage.

Suggested Citation

  • Xianjin Wang & Haotian Li & Yasu Chen & Ziqiang Wang & Xinxin Wu & Chen Zhu, 2025. "Modular access to alkylfluorides via radical decarboxylative-desulfonylative gem-difunctionalization," Nature Communications, Nature, vol. 16(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-60011-0
    DOI: 10.1038/s41467-025-60011-0
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