Free-radical carbo-alkenylation of N-aryl, N-benzyl, and N-phenethyl-ene-carbamates with a disulfone provides vinylsulfones which may then be functionalized and engaged in Heck-type coupling to furnish highly substituted 5-, 6-and 7-membered nitrogen heterocycles. Grignardmediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the aspidosperma family.