α-Haloarylsulfonamides: multiple cyclization pathways to skeletally diverse benzofused sultams

The development of new methods to skeletally diverse sultams based on a central α-halo benzene sulfonamide building block is reported. Several salient features of this building block are utilized in multiple reaction pathways, including the Heck reaction, C- and O-arylation, Sonogashira–Pauson–Khand, Sonogashira-intramolecular hydroamination, and domino aza-Michael–Heck for the generation of five-, six-, and seven-membered benzofused bicyclic and tricyclic sultams.