General Photo-Driven Chemoselective and Rapid Hydropentafluorosulfanylation of Alkenes via an Orchestrated Radical Chain Process
Although chain propagation strategies could accelerate molecular synthesis (e.g., Kharasch-type additions of fluorinated haloalkanes), controllable radical processes remain challenging. Herein, we develop a novel metal-free radical chain transformation that integrates radical addition, hydrogen atom transfer, and halogen atom transfer to enable hydropentafluorosulfanylation of alkenes. Our method exhibits a broad substrate scope across 73 substrates, including both activated and nonactivated alkenes, alkenes derived from natural products, and pharmaceutically relevant alkenes. This versatility enables the rapid synthesis of structurally diverse SF<sub>5</sub>-functionalized molecules. The biological and pharmaceutical applications are highlighted and demonstrated through cellular and in vivo experiments, thereby showcasing the synthetic utility of the developed methodology.
Authors
- Xiangyu Shen
- Xiao‐Song Xue (ORCID: https://orcid.org/0000-0003-4541-8702)
- Gang Wu (ORCID: https://orcid.org/0000-0002-0682-5172)
- Shuo Guo (ORCID: https://orcid.org/0000-0002-3042-9209)
- Jingwen Jiang (ORCID: https://orcid.org/0009-0006-9768-0314)
- Hui-Yi Yang (ORCID: https://orcid.org/0000-0002-6687-3694)
- Xiaolong Zhang (ORCID: https://orcid.org/0000-0002-0417-0002)
- Ning Zhang (ORCID: https://orcid.org/0000-0002-8781-4925)
- Wei Zhang (ORCID: https://orcid.org/0000-0003-3765-4908)
- Jiangshan Zhang (ORCID: https://orcid.org/0009-0007-7269-0011)
- Yongkang Jiang (ORCID: https://orcid.org/0000-0002-2768-6159)
- Donglei Sun (ORCID: https://orcid.org/0000-0002-3827-3982)
- Zhiwei Kuang
Institutions
- Sichuan University (CN)
- Inner Mongolia University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Institute for Advanced Study (DE)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-11-12
- DOI
- https://doi.org/10.1021/jacs.5c14406
- Citations
- 2
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.87