Iridium-catalyzed selective para-C-alkylation of anilines/phenols with aryl alkynes

Abstract

The general protocol for site-specific alkylation of anilines and phenols would provide an ideal strategy for affording densely functionalized aniline and phenol derivatives. Herein, we disclose a new iridium-catalyzed and acid-promoted process for selective para-alkylation of anilines and phenols using aryloxy or alkoxy aryl alkynes as the alkylated sources, delivering a wide range of para-C-alkylated phenols and anilines in good to excellent yields. The low catalyst loading (up to 0.05 mol%), scale-up of synthesis, operation under air conditions, as well as recycling of catalyst (5 times without deactivation) evidenced the promising application in organic synthesis.