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Peer-reviewedCC BY-NC-NDNature communications

Difunctionalization of unsaturated hydrocarbons via EDA complexes to access pentafluorosulfanyl thioethers.

  • Xiaofeng Zhang1
  • Yuanyang Jiang1
  • Hui-Yi Yang1
  • Yifan Ma1
  • Jiangshan Zhang1
  • Ning Zhang1
  • Gang Wu1
  • Donglei Sun2,3
  • Yi Shi3
  • Wei Zhang3
  • Shuaishuai Yue4
  • Shuo Guo5
1 more authors
  • Jianbo Wang6
6 affiliations
  1. 1Institute of Green Chemistry and Environment, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, 010021, P. R. China.
  2. 2Sichuan Tourism University, Chengdu, 610100, P. R. China.
  3. 3Molecular Toxicology Key Laboratory of Sichuan Provincial Education Office, Department of Hygienic Toxicology and Pathology, West China School of Public Health and West China Fourth Hospital, Sichuan University, Chengdu, 610041, China.
  4. 4Institute of Green Chemistry and Environment, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, 010021, P. R. China. [email protected].
  5. 5Institute of Green Chemistry and Environment, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, 010021, P. R. China. [email protected].
  6. 6Institute of Green Chemistry and Environment, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, 010021, P. R. China. [email protected].
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Abstract

Recently, the pentafluorosulfanyl (SF₅) group has attracted considerable interest from medicinal chemists owing to its capacity to significantly enhance the pharmaceutical properties of small-molecule drug candidates. However, a general method for three-component pentafluorosulfanylation of electron-deficient alkenes remains elusive. Herein, we present an electron donor-acceptor (EDA) complex photoactivation strategy for the thiopentafluorosulfanylation of unsaturated hydrocarbons, including electron-deficient alkenes, alkynes, 1,6-enynes, and even acetylene gas. The utility of this approach is demonstrated through the synthesis of a diverse array of pentafluorosulfanyl thioethers and the late-stage functionalization of complex molecules, including pharmaceuticals, natural products, and amino acid derivatives. This work establishes a framework for designing atom-economical difunctionalization reactions that employ green LEDs under mild conditions. Moreover, mechanistic studies support an EDA complex-mediated pathway and identify ArSCl as a key intermediate formed upon generation of the thiyl radical.

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Cite

BibTeXRIS
BibTeX
@article{zhang2026difunctionalization,
  title = {{Difunctionalization of unsaturated hydrocarbons via EDA complexes to access pentafluorosulfanyl thioethers.}},
  author = {Xiaofeng Zhang and Yuanyang Jiang and Hui-Yi Yang and Yifan Ma and Jiangshan Zhang and Ning Zhang and Gang Wu and Donglei Sun and Yi Shi and Wei Zhang and Shuaishuai Yue and Shuo Guo and Jianbo Wang},
  journal = {Nature communications},
  year = {2026},
  month = sep,
  doi = {10.1038/s41467-026-77739-y},
  url = {https://europepmc.org/article/MED/42875439},
  note = {CC BY-NC-ND},
}
RIS
TY  - JOUR
TI  - Difunctionalization of unsaturated hydrocarbons via EDA complexes to access pentafluorosulfanyl thioethers.
AU  - Xiaofeng Zhang
AU  - Yuanyang Jiang
AU  - Hui-Yi Yang
AU  - Yifan Ma
AU  - Jiangshan Zhang
AU  - Ning Zhang
AU  - Gang Wu
AU  - Donglei Sun
AU  - Yi Shi
AU  - Wei Zhang
AU  - Shuaishuai Yue
AU  - Shuo Guo
AU  - Jianbo Wang
PY  - 2026
DA  - 2026/09/14
JO  - Nature communications
DO  - 10.1038/s41467-026-77739-y
UR  - https://europepmc.org/article/MED/42875439
AB  - Recently, the pentafluorosulfanyl (SF₅) group has attracted considerable interest from medicinal chemists owing to its capacity to significantly enhance the pharmaceutical properties of small-molecule drug candidates. However, a general method for three-component pentafluorosulfanylation of electron-deficient alkenes remains elusive. Herein, we present an electron donor-acceptor (EDA) complex photoactivation strategy for the thiopentafluorosulfanylation of unsaturated hydrocarbons, including electron-deficient alkenes, alkynes, 1,6-enynes, and even acetylene gas. The utility of this approach is demonstrated through the synthesis of a diverse array of pentafluorosulfanyl thioethers and the late-stage functionalization of complex molecules, including pharmaceuticals, natural products, and amino acid derivatives. This work establishes a framework for designing atom-economical difunctionalization reactions that employ green LEDs under mild conditions. Moreover, mechanistic studies support an EDA complex-mediated pathway and identify ArSCl as a key intermediate formed upon generation of the thiyl radical.
SN  - 2041-1723
ER  -