Photocatalytic Fluorosulfonylation/Fluorosulfonamidation of <i>N</i>-Homoallyl Aldehyde Hydrazones to Access FSO<sub>2</sub>-/FSO<sub>2</sub>N-Functionalized Tetrahydropyridazines
Yichen Dong, Yu-Xue Ma, Yuan Lu, Qi Lin, Wei Li, Lijin Wang
Abstract
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 N -homoallyl aldehyde hydrazones using FABI (1-fluorosulfonyl-2-arylbenzoimidazolium triflate salts) and NFSAP ( N -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.