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

Carbon-nitrogen bond activation, via uranyl photoredox catalysis with water, enabled the conversion of 40 protogenetic anilines, 8 N-substituted anilines and 9 aniline-containing natural products/pharmaceuticals to the corresponding phenols in an ambient environment. A single-electron transfer process between a protonated aniline and uranyl catalyst, which was disclosed by radical quenching experiments and Stern-Volmer analysis, facilitated the following oxygen atom transfer process between the radical cation of protonated anilines and uranyl peroxide originating from water-splitting. O-18 labeling and N-15 tracking unambiguously depicted that the oxygen came from water and amino group left as ammonium salt. The 100-fold efficiency of the flow operation demonstrated the great potential of the conversion process for industrial synthetic application. From aniline to phenol: carbon-nitrogen bond activation and carbon-oxygen bond formation via uranyl photoredox catalysis with water at ambient environment.

Automated summary

This study demonstrates the efficient conversion of various anilines to phenols through uranyl photoredox catalysis with water. The protonated anilines undergo a single-electron transfer process with the uranyl catalyst, facilitating the oxygen atom transfer between the radical cation of protonated anilines and uranyl peroxide. Oxygen is sourced from water, while the amino groups are transformed into ammonium salts. The flow operation shows 100-fold efficiency, indicating the potential for industrial synthetic applications.