Plasma Electrochemistry for Carbon-Carbon Bond Formation via Pinacol Coupling
Journal of the American Chemical Society, vol.145, no.19, pp.10470-10474, 2023 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 145 Issue: 19
- Publication Date: 2023
- Doi Number: 10.1021/jacs.3c01779
- Journal Name: Journal of the American Chemical Society
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, Aqualine, Aquatic Science & Fisheries Abstracts (ASFA), Artic & Antarctic Regions, BIOSIS, Biotechnology Research Abstracts, Chemical Abstracts Core, Chimica, Compendex, Computer & Applied Sciences, EMBASE, MEDLINE, DIALNET
- Page Numbers: pp.10470-10474
- Middle East Technical University Affiliated: Yes
Abstract
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.