Electrooxidative Fluorofunctionalization of Arylcyclopropanes
Yanni Yue1,2, Yang Song1, Shuaishuai Zhao1
1Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), State Key Laboratory of Material-Oriented Chemical Engineering, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
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 BF4- counterion. By integrating alcohols, acids, and N-heterocycles as the terminating nucleophiles, straightforward 1,3-fluorooxygenation and 1,3-fluoroamination are smoothly achieved.
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