Substrate-Controlled Pentafluorosulfanylation of Activated Alkenes Containing the Benzimidazole Moiety with SF<sub>5</sub>Cl
We report herein a method of substrate-controlled pentafluorosulfanylation of activated alkenes containing the benzimidazole moiety with SF<sub>5</sub>Cl, which provides a highly efficient way to access SF<sub>5</sub>-containing benzo[4,5]imidazole[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-ones, as well as SF<sub>5</sub>-containing <i>N</i>-benzoyl benzimidazoles. Besides the pentafluorosulfanyl group (-SF<sub>5</sub>), the current method can be applied to the tetrafluorosulfanyl group (-SF<sub>4</sub>-) incorporation. A radical mechanism involving single electron transfer (SET) or the atom transfer radical addition (ATRA) process is proposed.
Authors
- Yuezhen Li
- Ping‐Xin Zhou
- Yingling Wang
- Lizhen Fang (ORCID: https://orcid.org/0000-0001-8594-4710)
- Yingchang Guo
- Xinqiang Tan (ORCID: https://orcid.org/0000-0003-2200-9340)
- Hao Tang (ORCID: https://orcid.org/0000-0003-0323-0349)
- Rong Fan (ORCID: https://orcid.org/0000-0002-3388-0847)
- Shijie Liu (ORCID: https://orcid.org/0000-0003-1085-0722)
- Yunhui Yan (ORCID: https://orcid.org/0000-0002-6961-6765)
- Jianmei Yuan
- Ziyou Hao
Institutions
- Wenzhou University (CN)
- Division of Materials Science and Engineering (AU)
- Henan Medical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-14
- DOI
- https://doi.org/10.1021/acs.joc.5c00103
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.37
Funders
- Natural Science Foundation of Henan Province
- Xinxiang Medical University