From aniline to phenol: carbon-nitrogen bond activation via uranyl photoredox catalysis

Abstract

Abstract Carbon-nitrogen bond activation, via uranyl photoredox catalysis with water, enabled the conversion from 40 protogenetic anilines, 8 N-substituted anilines, and 9 aniline-containing natural products/pharmaceuticals to the corresponding phenols at ambient environment. Single electron transfer process between protonated aniline and uranyl catalyst, which was disclosed by radical quenching experiments and Stern-Volmer analysis, facilitated the following oxygen atom transfer process between radical cation of protonated anilines and uranyl peroxide originating from water-splitting. 18O labelling and 15N tracking unambiguously depicted that the oxygen came from water and amino group leaved as ammonium salt. Hundredfold efficiency of flow operation demonstrated the great potential of the conversion process in industrial synthetic application.