An Electrochemical Approach to Directed Fluorination
Eric Holt, Muyuan Wang, Stefan Andrew Harry, Chengkun He, Yuang Wang, Nicolas Henriquez, Michael Richard Xiang, Andrea Zhu, Fereshte Ghorbani, Thomas Lectka
Abstract
Electrosynthesis has made a revival in the field of organic chemistry and, in particular, radical-mediated reactions. Herein, we report a simple directed, electrochemical C-H fluorination method. Employing a dabconium mediator, commercially available Selectfluor, and RVC electrodes, we provide a range of steroid-based substrates with competent regioselective directing groups, including enones, ketones, and hydroxy groups, as well as never reported before lactams, imides, lactones, and esters.
Topics & Concepts
SelectfluorElectrosynthesisRegioselectivityElectrochemistryChemistryCombinatorial chemistryOrganic chemistrySteroidElectrodeCatalysisBiochemistryHormonePhysical chemistryFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods