Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates.

Qiang Wang Maria Biosca Fahmi Himo Kálmán J Szabó

Published in: Angewandte Chemie (International ed. in English) (2021)

The electrophilic fluorination of geminal alkyl substituted vinyl-Bmida derivatives proceeds via bora-Wagner-Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora-cyclopropane shaped TS. The Bmida group has a larger migration aptitude than the alkyl moiety in the Wagner-Meerwein rearrangement of the presented electrophilic fluorination reactions.

Keyphrases

ionic liquid
molecular docking
density functional theory
molecular dynamics
visible light