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- Title
Electrochemical Fluorination of Vinyl Boronates through Donor‐Stabilized Vinyl Carbocation Intermediates**.
- Authors
Wigman, Benjamin; Lee, Woojin; Wei, Wenjing; Houk, Kendall N.; Nelson, Hosea M.
- 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.
- Subjects
FLUORINATION; FLUOROETHYLENE; CARBOCATIONS; NUCLEOPHILES; BORONIC esters; BORONIC acids; OXIDATION
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 12, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202113972