Oxidation and reduction reactions are among the most important and frequently executed processes in organic synthesis. However, our ability to manipulate the oxidation states of functional groups in complex settings with high efficiency, precision, and minimal waste remains in a largely nascent stage. Owing to its many distinct characteristics, electrochemistry represents an attractive approach to meet the prevailing trends in organic synthesis. In particular, electrocatalysis—a process that integrates electrochemistry and small-molecule catalysis—has the potential to substantially improve the scope of synthetic electrochemistry and provide a wide range of useful transformations. Despite its attractive attributes and extensive applications in energy-related fields, electrocatalysis has been used only sparingly in synthetic organic chemistry. Thus, there exists a clear impetus for inventing new catalytic strategies to improve the scope of synthetic electrochemistry and provide new platforms for reaction discovery and synthetic innovations. Toward this end, we developed a new catalytic approach that combines electrochemistry and redox-metal catalysis for the oxidative difunctionalization of alkenes to access a diverse array of vicinally functionalized structures. This presentation will detail our design principle underpinning the development of electrocatalytic alkene diazidation, dichlorination, halotrifluoromethylation, and haloalkylation.

Using electricity to amp up organic synthesis: Electrocatalytic alkene difunctionalization

2019 Spring National Meeting

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