Kilo-Scale Electrochemical Oxidation of a Thioether to a Sulfone: A Workflow for Scaling up Electrosynthesis

• DOI: 10.1021/acs.oprd.2c00111
• Publication Date: 2022-07-01T12:00:51Z
• Authors: Cecilia Bottecchia; Dan Lehnherr; François Lévesque; Mikhail Reibarkh; Yining Ji; Vailankanni L. Ro...; Heather Wang; Yu-hong Lam; Thomas P. Vickery; Brittany M. Armst...; Keith A. Mattern; Kevin Stone; Michael K. Wismer; Andrew N. Singh; Erik L. Regalado; Kevin M. Maloney; Neil A. Strotman
• Keywords: Electrosynthesis; Thioether; Organic Synthesis; Flow chemistry

Organic electrosynthesis is a rapidly evolving field, providing powerful methods to assemble targets of interest in organic synthesis. Concerns around the scalability electrochemical remain biggest reason behind their scarce implementation manufacturing routes for pharmaceutical industry. To fill this gap, we report workflow describing key reaction parameters toward successful scale-up an electrosynthetic method from milligram kilogram scale. The used demonstrate our and flow setting was oxidation thioether its corresponding sulfone, fragment active ingredient under development. use online nuclear magnetic resonance spectroscopy, offline ion chromatography, cyclic voltammetry, density functional theory calculations provided insight into mechanism side reactions.