Visible‐Light Photoredox‐Catalyzed C−H Difluoroalkylation of Hydrazones through an Aminyl Radical/Polar Mechanism |
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| Authors: | Pan Xu Guoqiang Wang Yuchen Zhu Weipeng Li Prof Dr Yixiang Cheng Prof Dr Shuhua Li Prof Dr Chengjian Zhu |
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| Institution: | 1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, P. R. China;2. Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, P. R. China;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, P. R. China |
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| Abstract: | An unprecedented visible‐light‐induced direct C?H bond difluoroalkylation of aldehyde‐derived hydrazones was developed. This reaction represents a new way to synthesize substituted hydrazones. The salient features of this reaction include difluorinated hydrazone synthesis rather than classical amine synthesis, extremely mild reaction conditions, high efficiency, wide substrate scope, ease in further transformations of the products, and one‐pot syntheses. Mechanistic analyses and theoretical calculations indicate that this reaction is enabled by a novel aminyl radical/polar crossover mechanism, with the aminyl radical being oxidized into the corresponding aminyl cation through a single electron transfer (SET) process. |
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| Keywords: | fluorine hydrazones imines photocatalysis radical reactions |
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