Related Experiment Video
Updated: Sep 25, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Synthesis of Aryl Perfluorocyclopropyl Ethers via [2 + 1] Cyclopropanation Using TMSCF2Br Reagent
1Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China.
Abstract:
Aryl perfluorocyclopropyl ethers have been synthesized for the first time by [2 + 1] cyclopropanation between aryl trifluorovinyl ethers and a commercially available TMSCF2Br reagent. This cycloaddition reaction between two fluorine-containing reactants proceeds smoothly in toluene at 120 °C in the presence of a catalytic amount of n-Bu4NBr, and the reaction tolerates a variety of functional groups. A wide range of aryl trifluorovinyl ethers, easily accessible from phenols, were successfully transformed to aryl perfluorocyclopropyl ethers.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Cycloaddition Reactions: Overview
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Radical Substitution: Allylic Bromination
Cycloaddition Reactions: MO Requirements for Thermal Activation
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

