Aerobic Copper-Catalyzed Salicylaldehydic C -H Arylations with Arylboronic Acids.

We report a challenging copper-catalyzed C -H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the C -H bond compared to the phenolic O-H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a Cu /Cu /Cu catalytic cycle.