Abstract
N-(Organodithio)phthalimides have attracted significant attention as versatile disulfide transfer reagents, but their applications have been largely limited to substitution reactions with highly reactive nucleophiles. We report a Lewis base-catalyzed activation strategy that expands the scope of N-(organodithio)phthalimides to the bifunctionalization of less reactive olefins. Nucleophile-tethered olefins undergo smooth cyclization to furnish heterocycle-appended disulfides. With broad substrate scope and the ready availability of N-(organodithio)phthalimides from bilateral reagents, this strategy enables modular construction of unsymmetrical disulfides.