Samarium diiodide-mediated intermolecular coupling of organic halides with cyclic imides

SmI2-mediated couplings between a variety of organic halides and cyclic imides have been performed giving either hydroxylactams from N-methylsuccinimide and N-methylphthalimide or δ-ketoamides from N-methylglutarimide. In the latter case, ring opening occurs during hydrolysis. Couplings of imides with alkyl halides require a catalytic amount of NiI2.