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Radical–Polar Crossover Reactions: Oxidative Coupling of 1,3-Dioxolanes with Electron-Deficient Alkenes and Vinylarenes Based on a Radical Addition and Kornblum–DeLaMare Rearrangement

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journal contribution
posted on 19.12.2014, 00:00 by Peng Du, Huihuang Li, Yaxiong Wang, Jiang Cheng, Xiaobing Wan
A new radical-polar crossover reaction has been developed involving the combination of a tandem radical reaction and Kornblum–DeLaMare rearrangement in a one-pot process. This simple methodology allows for the construction of polyfunctionalized carbonyl compounds via the oxidative coupling of 1,3-dioxolanes with electron-deficient alkenes and vinylarenes in the presence of Co­(salen) and TBHP under mild conditions. This reaction also exhibited high functional group tolerance, wide substrate scope, and operational simplicity.