Traditional methods for vicinal functionalization rely on pre-installation of alkenes. However, C−H functionalization can serve as a strategy to introduce vicinal functional groups in a streamlined fashion. Toward this goal, a strategy has been developed that allows for regioselective difunctionalization by forming an alkene <i>in-situ</i> from inert C−H bonds. Polar addition across the newly generated alkene affords the desired difunctionalized product. Mechanistic investigation suggest that the alkene formation is mediated by an ion-pair interaction. This versatile strategy allows access to a family of products via a facile S<sub>N</sub>2 displacement protocol and will greatly streamline syntheses of complex products.

C−H functionalization of alcohols via radical-polar crossover

2019 Fall National Meeting

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