Electrochemical Fluorination of Vinyl Boronates through Donor‐Stabilized Vinyl Carbocation Intermediates**
Benjamin Wigman, Woojin Lee, Wenjing Wei, K. N. Houk, Hosea M. Nelson
Abstract
The electrochemical generation of vinyl carbocations from alkenyl boronic esters and boronates is reported. Using easy-to-handle nucleophilic fluoride reagents, these intermediates are trapped to form fully substituted vinyl fluorides. Mechanistic studies support the formation of dicoordinated carbocations through sequential single-electron oxidation events. Notably, this electrochemical fluorination features fast reaction times and Lewis acid-free conditions. This transformation provides a complementary method to access vinyl fluorides with simple fluoride salts such as TBAF.
Topics & Concepts
CarbocationElectrochemistryChemistryFluorideNucleophileReagentBoronic acidLewis acids and basesOrganic chemistryCombinatorial chemistryInorganic chemistryCatalysisElectrodePhysical chemistryFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods