A selective photoinduced radical O-alkenylation of phenols and naphthols with terminal alkynes

Abstract

The visible light-promoted O-alkenylation of phenols and naphthols with terminal alkynes is achieved using 2,4,6-tris(4-fluorophenyl)pyrylium tetrafluoroborate (T(p-F)PPT) as a photocatalyst at room temperature without the need of any external ligand or additive. Apart from its excellent functional group tolerance, the protocol described herein represents an appealing alternative strategy to classical transition-metal catalysed hydroarylation reactions. Mechanistic investigations revealed that the reaction involves a radical pathway. The utility of the hydroarylated products for the synthesis of fused benzofurans via a one-pot annulation was also demonstrated. Herein, we report the first intermolecular radical hydroarylation of alkynes.