학술논문

From aniline to phenol: carbon-nitrogen bond activation via uranyl photoredox catalysis.
Document Type
Article
Source
National Science Review. Jun2022, Vol. 9 Issue 6, p1-7. 7p.
Subject
*ANILINE
*PHENOL
*RADICAL cations
*AMINO group
*PHENOLS
Language
ISSN
2095-5138
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 great potential of the conversion process for industrial synthetic application. [ABSTRACT FROM AUTHOR]