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Transition-Metal-Free Allylic Defluorination Cross-Electrophile Coupling Employing Rongalite
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  • Xiang-Long Chen,
  • Chun-Yan Wu,
  • Dong-Sheng Yang,
  • Bo-Cheng Tang,
  • Huai-Yu Wang,
  • Zhi-Cheng Yu,
  • Anling Li,
  • Yan-Dong Wu,
  • Anxin Wu
Xiang-Long Chen
Central China Normal University
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Chun-Yan Wu
Central China Normal University
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Dong-Sheng Yang
Central China Normal University
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Bo-Cheng Tang
The Hong Kong Polytechnic University
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Huai-Yu Wang
Central China Normal University
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Zhi-Cheng Yu
Central China Normal University
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Anling Li
Zhongnan Hospital of Wuhan University
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Yan-Dong Wu
Central China Normal University
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Anxin Wu
Central China Normal University

Corresponding Author:chwuax@mail.ccnu.edu.cn

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Abstract

The conversion of CF3-alkenes to gem-difluoroalkenes using reductive cross-coupling strategy has received much attention in recent years, however, the use of green and readily available reducing salt to mediate these reactions remains to be explored. In this work a concise construction of gem-difluoroalkenes, which requires neither a catalyst nor a metal reducing agent, was established. Rongalite, a safe and inexpensive industrial product, was employed as both a radical initiator and reductant. This procedure was compatible with both linear and cyclic diaryliodonium salts, enabling a wide variety of substrates (>70 examples). The utility of this approach was demonstrated through gram-scale synthesis and efficient late-stage functionalizations of anti-inflammatory drugs.
Submitted to Chinese Journal of Chemistry
02 Feb 2024Review(s) Completed, Editorial Evaluation Pending
02 Feb 2024Editorial Decision: Accept
23 Feb 2024Published in Chinese Journal of Chemistry. https://doi.org/10.1002/cjoc.202300751