Photocatalytic Fluorosulfonylation/Fluorosulfonamidation of <i>N</i>-Homoallyl Aldehyde Hydrazones to Access FSO<sub>2</sub>-/FSO<sub>2</sub>N-Functionalized Tetrahydropyridazines
Sulfonyl/sulfamoyl fluoride and tetrahydropyridazine cores represent pivotal structural units in chemical and medicinal science. We herein disclose a photocatalytic strategy for the fluorosulfonylation/fluorosulfonamidation of <i>N</i>-homoallyl aldehyde hydrazones using FABI (1-fluorosulfonyl-2-arylbenzoimidazolium triflate salts) and NFSAP (<i>N</i>-fluorosulfamoylpyridinium salts), enabling efficient access to sulfonyl-/sulfamoyl-substituted tetrahydropyridazines. This protocol demonstrates excellent synthetic scalability and facilitates diverse postderivatization reactions, including SuFEx click reactions and elimination processes. Preliminary mechanistic studies reveal that the transformation proceeds via a fluorosulfonyl/fluorosulfonamidyl radical-mediated cascade cyclization pathway.
Authors
- Qi Lin (ORCID: https://orcid.org/0000-0002-3786-3593)
- Wei Li (ORCID: https://orcid.org/0000-0001-5069-5945)
- Yuan Lu (ORCID: https://orcid.org/0000-0003-2347-2521)
- Yichen Dong (ORCID: https://orcid.org/0000-0003-2280-4248)
- Lijin Wang
- Yu-Xue Ma
Institutions
- Ministry of Education of the People's Republic of China (CN)
- Hebei University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c02385
- Citations
- 3
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 2.81