电合成
硫醚
循环伏安法
电化学
有机合成
工作流程
化学
流动化学
计算机科学
组合化学
工艺工程
有机化学
电极
催化作用
物理化学
数据库
工程类
作者
Cecilia Bottecchia,Dan Lehnherr,François Lévesque,Mikhail Reibarkh,Yining Ji,Vailankanni L. Rodrigues,Heather Wang,Yu-hong Lam,Thomas P. Vickery,Brittany M. Armstrong,Keith Mattern,Kevin Stone,Michael K. Wismer,Andrew N. Singh,Erik L. Regalado,Kevin M. Maloney,Neil A. Strotman
标识
DOI:10.1021/acs.oprd.2c00111
摘要
Organic electrosynthesis is a rapidly evolving field, providing powerful methods to assemble targets of interest in organic synthesis. Concerns around the scalability of electrochemical methods remain the biggest reason behind their scarce implementation in manufacturing routes for the pharmaceutical industry. To fill this gap, we report a workflow describing the key reaction parameters toward the successful scale-up of an organic electrosynthetic method from milligram to kilogram scale. The reaction used to demonstrate our workflow and scale-up in a flow setting was the oxidation of a thioether to its corresponding sulfone, a fragment of interest in an active pharmaceutical ingredient under development. The use of online flow nuclear magnetic resonance spectroscopy, offline ion chromatography, cyclic voltammetry, and density functional theory calculations provided insight into the reaction mechanism and side reactions.
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