Triarylphosphines Drive Azine C–H Coupling With 2 Abundant Reagents, Water and Ammonia
Updated
Updated · Nature.com · Aug 11
Triarylphosphines Drive Azine C–H Coupling With 2 Abundant Reagents, Water and Ammonia
1 articles · Updated · Nature.com · Aug 11
Summary
Nature reports that simple triarylphosphines can selectively couple azine C–H bonds with water and ammonia, a rare route to direct C–O and C–N bond formation.
A distinct P(V)-based mechanism underpins the chemistry: pendant aldehyde and imine groups interconvert into acetal- and aminal-type forms that deliver water or ammonia into the reactive coordination environment.
A broad substrate scope includes pyridines, quinolines and diazines, extending the method beyond a narrow model system.
Late-stage hydroxylation and amination of complex pharmaceutical and agrochemical molecules suggest the reaction could aid structure-activity studies where direct C–H editing is valuable.
The work points beyond transition metals, whose incompatibility with water and ammonia has limited such coupling reactions despite both reagents being abundant.