State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. China.
Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. China.
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2939-43. doi: 10.1002/anie.201508698. Epub 2015 Nov 23.
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.
发展了一种前所未有的可见光诱导的醛衍生腙的直接 C-H 键双氟烷基化反应。该反应代表了合成取代腙的新方法。该反应的显著特点包括合成二氟代腙而不是经典的胺合成、极其温和的反应条件、高效率、广泛的底物范围、产物的进一步转化容易以及一锅合成。机理分析和理论计算表明，该反应是通过一种新的氨自由基/极性交叉机制实现的，其中氨自由基通过单电子转移（SET）过程被氧化成相应的氨阳离子。
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