Halonium Ion Triggered Rearrangement of Unsaturated Benzo-Annulated Bi- and Tricyclic Sulfonamides

The halonium ion mediated 1,2-Wagner–Meerwein-type rearrangement of a series of benzo-fused bi- and tricyclic sulfonamides is reported. During this rearrangement the carbon–carbon bond that migrates was selectively set in the intramolecular Mizoroki–Heck (IHR) synthesis of the starting materials. Consequently, this method constitutes a means to access the regioisomeric series of cyclic sulfonamides not observed during the Mizoroki–Heck reaction.