Organoselenium and DMAP co-catalysis: Regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes

Article abstract of DOI:10.1039/c5cc10245f

A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. ⁷⁷Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.