Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation

Abstract

In this work, we present a room- or solar-light-initiated transition-metal-free radical homolytic aromatic substitution (HAS) reaction of aniline derivatives with perfluoroalkyl moieties employing perfluoroalkyl halides as readily available perfluoroalkyl sources in the presence of cesium carbonate as base and inexpensive Rose Bengal as organophotocatalyst in MeCN as solvent, rendering perfluoroalkyl-substituted aniline derivatives in good-to-excellent yields, even upon scaling up. Although the mechanism of this reaction is still under investigation, we shall present some evidence based on competitive substitution rate experiments that cast some light onto the reaction intermediates.