Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons

Copper-catalyzed Sonogashira-type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5mol% < Cu < 5mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation, affording respectable yields of the desired products. The novel Cu(OTf)(2)/pyrene system was subsequently employed to synthesize phenylacetylene-based fluorescent compounds. Copyright (c) 2015 John Wiley & Sons, Ltd.