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

ABSTRACT: 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. ¹⁸O labeling and ¹⁵N 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

SUBMITTER: Hu D 

PROVIDER: S-EPMC9283103 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature