Metal-free visible-light-induced photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes

Reported here is an intermolecular pyridylation/phosphinoylation of alkenes using 4-cyanopyridine and diphenylphosphine oxide under visible-light-induced organic photoredox catalysis. The reaction occurs under mild metal-free conditions, possessing a broad substrate scope. The protocol can be practiced on a gram scale and applied to the modification of natural product-derived and medicinally relevant complex molecules containing a styrene unit. Mechanistic investigations suggest that triethylamine serves as both single-electron transfer (SET) and hydrogen atom transfer (HAT) agents.

Automated summary

The reported reaction utilizes organic photoredox catalysis to achieve intermolecular pyridylation/phosphinoylation of alkenes, with broad substrate scope under mild metal-free conditions, suitable for gram-scale production and modification of medicinal molecules. Mechanistic investigations indicate that triethylamine functions as both single-electron transfer (SET) and hydrogen atom transfer (HAT) agents in the reaction.