Dual ipso-hydroxylation and para-C–H chalcogenation of arylboronic acids using an NDI photocatalyst in visible light

Abstract

We report a dual ipso-hydroxylation and para-C–H chalcogenation of arylboronic acids using NDI-PC as a photocatalyst in visible light. para-Selective C–H thiocyanation, selenocyanation, thiophenylation, and selenophenylation of phenols, generated in situ from arylboronic acids, has been achieved via a photoredox process in the presence of air as the oxidant. This method is transition-metal free, sustainable, and gives the products in moderate to high yields at room temperature.