Hu Deqing, Zhou Yilin, Jiang Xuefeng
Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
Natl Sci Rev. 2021 Aug 20;9(6):nwab156. doi: 10.1093/nsr/nwab156. eCollection 2022 Jun.
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 labeling and N 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.
通过铀酰光氧化还原催化与水实现的碳氮键活化，能够在环境条件下将40种原生苯胺、8种N-取代苯胺以及9种含苯胺的天然产物/药物转化为相应的酚类。质子化苯胺与铀酰催化剂之间的单电子转移过程，这一过程通过自由基猝灭实验和斯特恩-沃尔默分析得以揭示，促进了质子化苯胺的自由基阳离子与源自水分解的过氧化铀酰之间随后的氧原子转移过程。氧标记和氮追踪明确表明氧来自水，氨基以铵盐形式离去。流动操作提高100倍的效率证明了该转化过程在工业合成应用中的巨大潜力。
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