Plasma Electrochemistry for Carbon-Carbon Bond Formation via Pinacol Coupling

Wang J., ÜNER N. B., Dubowsky S. E., Confer M. P., Bhargava R., Sun Y., ...Daha Fazla

Journal of the American Chemical Society, cilt.145, sa.19, ss.10470-10474, 2023 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 145 Sayı: 19
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1021/jacs.3c01779
  • Dergi Adı: Journal of the American Chemical Society
  • Derginin Tarandığı İndeksler: 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
  • Sayfa Sayıları: ss.10470-10474
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.