Exploring Eosin Y as a bimodular catalyst: organophotoacid mediated Minisci-type acylation of <i>N</i>-heteroarenes

Abstract

Here we report Eosin Y as a bimodular catalyst for Minisci-type acylation reactions. The formation of organic exciplexes between photoexcited Eosin Y and <i>N</i>-heteroarenes was found to be a stabilizing factor for photoacid catalysis under optimized conditions. Spectroscopic investigations such as steady state fluorescence quenching and dynamic lifetime quenching experiments were employed to better understand the role of Eosin Y as both a photoredox catalyst and a photoacid. Feedstock aldehydes were employed as acyl radical precursors for engaging in C-C bond formation reactions with a variety of nitrogen containing heterocycles.