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Unified metal-free intermolecular Heck-type sulfonylation, cyanation, amination, amidation of alkenes by thianthrenation

Author

Listed:
  • Ming-Shang Liu

    (Southern University of Science and Technology)

  • Hai-Wu Du

    (Southern University of Science and Technology
    Nankai University)

  • Huan Meng

    (Southern University of Science and Technology)

  • Ying Xie

    (Sichuan University of Science and Engineering)

  • Wei Shu

    (Southern University of Science and Technology
    Nankai University
    Sichuan University of Science and Engineering)

Abstract

Direct and site-selective C-H functionalization of alkenes under environmentally benign conditions represents a useful and attractive yet challenging transformation to access value-added molecules. Herein, a unified protocol for a variety of intermolecular Heck-type functionalizations of Csp2-H bond of alkenes has been developed by thianthrenation. The reaction features metal-free and operationally simple conditions for exclusive cine-selective C-H functionalization of aliphatic and aryl alkenes to forge C-C, C-N, C-P, and C-S bonds at room temperature, providing a general protocol for intermolecular Heck-type reaction of alkenes with nucleophiles (Nu = sulfinates, cyanides, amines, amides). Alkenes undergo cine-sulfonylation, cyanation, amination to afford alkenyl sulfones, alkenyl nitriles and enamines.

Suggested Citation

  • Ming-Shang Liu & Hai-Wu Du & Huan Meng & Ying Xie & Wei Shu, 2024. "Unified metal-free intermolecular Heck-type sulfonylation, cyanation, amination, amidation of alkenes by thianthrenation," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-44746-w
    DOI: 10.1038/s41467-024-44746-w
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