The intermolecular hydroarylation of pyridine units with simple alkenes has been achieved using a photoredox radical mechanism. The regiospecific single-electron reduction of halogenated pyridines with a commercially available iridium catalyst, followed by radical addition to unactivated alkene substrates, occurs with exclusive anti-Markovnikov selectivity. A complementary system for the regioselective synthesis of arylethylamines via aryl radicals was developed using a unique dual organocatalytic system. The photoinduced reduction of aryl halides and intermolecular coupling to vinylamine derivatives afforded a wide range of arylethylamine structures. Both systems are mild, scalable, tolerant of many functional groups, and effective for the preparation of a wide range of medicinally relevant scaffolds with complete regiocontrol.

Selective intermolecular couplings of aryl radical species with olefins

2019 Fall National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.