Electrochemical Fluorination of Vinyl Boronates Through Donor-Stabilized Vinyl Carbocation Intermediates

19 August 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The electrochemical generation of vinyl carbocations from vinyl boronic esters and boronates is reported. Using easy-to-handle nucleophilic fluoride reagents, these intermediates are trapped to form fully substituted vinyl fluorides. Mech-anistic studies support the formation of dicoordinated car-bocations through sequential single-electron oxidation events. Notably, this electrochemical fluorination features fast reaction times and mild conditions. This transfor-mation provides a complementary method to access vinyl fluorides with simple fluoride salts such as TBAF.


radical-polar crossover
nucleophilic fluorination
Vinyl carbocation


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