Insertion of Arynes into the C–C σ-Bond of α-Pentafluorosulfanyl Ketones: Access to 2-(Pentafluorosulfanyl)methyl Benzophenones
The incorporation of the pentafluorosulfanyl (SF<sub>5</sub>) group into organic molecules is highly significant due to its unique physicochemical properties and potential applications in pharmaceuticals and agrochemicals. However, general and efficient methods for the synthesis of benzylic SF<sub>5</sub>-containing compounds remain unexplored. Herein, we report the synthesis of a series of 2-(pentafluorosulfanyl)methyl benzophenones via the insertion of arynes into the C-C σ-bond of α-pentafluorosulfanyl ketones. This transition-metal-free reaction proceeds under mild conditions with high regioselectivity and good functional group tolerance, as demonstrated by 21 examples.
Authors
- Feng‐Ling Qing (ORCID: https://orcid.org/0000-0002-7082-756X)
- Zeguo Fang (ORCID: https://orcid.org/0000-0002-4844-1476)
- M. Nuruzzaman Khan (ORCID: https://orcid.org/0000-0002-7269-3323)
- Xin Jia (ORCID: https://orcid.org/0000-0001-6520-5275)
- Jia‐Yi Shou
- Xu-Biao He
Institutions
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Hubei University of Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-30
- DOI
- https://doi.org/10.1021/acs.joc.5c00759
- Citations
- 5
- Primary Topic
- Cyclization and Aryne Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- National Natural Science Foundation of China
- Hubei University of Technology
- National Key Research and Development Program of China