Pentafluorosulfanylation of Acrylamides: The Synthesis of SF<sub>5</sub>-Containing Isoquinolinediones with SF<sub>5</sub>Cl
We disclose herein an efficient and facile method for the synthesis of SF<sub>5</sub>-containing isoquinolinediones with an all-carbon quaternary stereocenter via intramolecular pentafluorosulfanylation of acrylamides using SF<sub>5</sub>Cl as a pentafluorosulfanylation reagent. The protocol proceeds under mild reaction conditions and enjoys a broad substrate scope, wide functional group compatibility, and high atom- and step-economy. A radical mechanism involving the SF<sub>5</sub> radical cascade addition/cyclization of acrylamides is proposed.
Authors
- Yuezhen Li
- Ping‐Xin Zhou
- Yingling Wang
- Lizhen Fang (ORCID: https://orcid.org/0000-0001-8594-4710)
- Xinqiang Tan (ORCID: https://orcid.org/0000-0003-2200-9340)
- Bingqing Liu (ORCID: https://orcid.org/0000-0002-1540-2235)
- Jia Wang (ORCID: https://orcid.org/0000-0002-6237-8434)
- Xiangqian Liu (ORCID: https://orcid.org/0000-0001-9249-2206)
- Jianmei Yuan
- Ziyou Hao
Institutions
- Henan Medical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-24
- DOI
- https://doi.org/10.1021/acs.joc.4c02181
- Citations
- 7
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.46
Funders
- Natural Science Foundation of Henan Province
- Xinxiang Medical University