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Plasma Electrochemistry for Carbon-Carbon Bond Formation via Pinacol Coupling.

Jian WangNecip B ÜnerScott Edwin DubowskyMatthew P ConferRohit BhargavaYunyan SunYuting ZhouR Mohan SankaranJeffrey S Moore
Published in: Journal of the American Chemical Society (2023)
The formation of carbon-carbon bonds by pinacol coupling of aldehydes and ketones requires a large negative reduction potential, often realized with a stoichiometric reducing reagent. Here, we use solvated electrons generated via a plasma-liquid process. Parametric studies with methyl-4-formylbenzoate reveal that selectivity over the competing reduction to the alcohol requires careful control over mass transport. The generality is demonstrated with benzaldehydes, benzyl ketones, and furfural. A reaction-diffusion model explains the observed kinetics, and ab initio calculations provide insight into the mechanism. This study opens the possibility of a metal-free, electrically-powered, sustainable method for reductive organic reactions.
Keyphrases
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