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From aniline to phenol: carbon-nitrogen bond activation via uranyl photoredox catalysis
National Science Review ( IF 16.3 ) Pub Date : 2021-08-18 , DOI: 10.1093/nsr/nwab156
Deqing Hu 1 , Yilin Zhou 1 , Xuefeng Jiang 1
Affiliation  

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.

中文翻译:

从苯胺到苯酚:铀酰光氧化还原催化碳-氮键活化

通过与水的铀酰光氧化还原催化的碳-氮键活化,使 40 种原生苯胺、8 种 N 取代苯胺和 9 种含苯胺的天然产物/药物能够在环境环境中转化为相应的酚类。自由基猝灭实验和Stern-Volmer分析揭示了质子化苯胺和铀酰催化剂之间的单电子转移过程,促进了质子化苯胺自由基阳离子与源自水分解的过氧化铀酰之间的氧原子转移过程。18O 标记和 15N 追踪清楚地描述了氧来自水和氨基作为铵盐离开。数百倍的流动操作效率显示了转化过程在工业合成应用中的巨大潜力。
更新日期:2021-08-18
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