Regioselective Multicomponent Sulfonylation/Cyclization of Unactivated Alkenes to Access Sulfonylated Six- and Seven-Membered Cyclic Enamines via SO<sub>2</sub> Insertion
Radical cascade cyclization of alkenes involving the insertion of sulfur dioxide has proven to be a promising tool to access sulfonylnated heterocycle compounds, whereas cyclization of unactivated alkenes has been much less explored. Here, we developed a three-component cascade of unactive alkenes with sulfur dioxide and aryldiazonium tetrafluoroborates to generate sulfonylated tetrahydropyridines and azepines via the cleavage of alkenyl C-H bonds. Moreover, this protocol exhibited excellent chemical and regioselectivity and compatibility with broad functional groups.
Authors
- Hui Gao (ORCID: https://orcid.org/0000-0001-5620-0958)
- Zirong Li
- Shu Min Tao (ORCID: https://orcid.org/0000-0002-7374-7063)
- Ran Ding (ORCID: https://orcid.org/0000-0002-1087-6407)
- Nianshou Cheng (ORCID: https://orcid.org/0000-0003-4331-829X)
- Lei Liu (ORCID: https://orcid.org/0000-0001-6364-3634)
- Yu Guo (ORCID: https://orcid.org/0000-0003-4952-8431)
- Pan-Ya Cui
Institutions
- University of Science and Technology of China (CN)
- Huaibei Normal University (CN)
- Anhui University of Science and Technology (CN)
- Anhui Science and Technology University (CN)
- Division of Materials Science and Engineering (AU)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-01
- DOI
- https://doi.org/10.1021/acs.joc.5c01403
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00