Electrooxidative Fluorofunctionalization of Arylcyclopropanes
Yanni Yue, Yang Song, Shuaishuai Zhao, Chi Zhang, Chuan Zhu, Chao Feng
Abstract
The work herein demonstrates the viability of an electrochemical oxidative protocol for the expedient realization of 1,3-fluorofunctionalization of arylcyclopropanes under catalyst- and oxidant-free conditions. Given the relatively low nucleophilicity of fluoride ion, the counterintuitive outcome that the ring-opening is initiated by nucleophilic fluorination is rationalized by invoking tight ion pair between aryl radical cation and BF 4 – counterion. By integrating alcohols, acids, and N-heterocycles as the terminating nucleophiles, straightforward 1,3-fluorooxygenation and 1,3-fluoroamination are smoothly achieved.
Topics & Concepts
ChemistryNucleophileCounterionCatalysisArylFluorideElectrochemistryCombinatorial chemistryRing (chemistry)FluorineIonOrganic chemistryMedicinal chemistryComputational chemistryInorganic chemistryAlkylPhysical chemistryElectrodeCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques