Direct Transformation of Tetrafluoroethylene to Trifluorovinylzinc via sp² C–F Bond Activation

Abstract

Trifluorovinylzinc is a common synthetic intermediate for trifluorovinyl derivatives, including α,β,β-trifluorostyrenes and hexafluorobutadiene. Here, we report a novel synthetic approach for the formation of trifluorovinylzinc chloride via a C–F bond activation of tetrafluoroethylene (TFE), which is an industrially cost-effective bulk feedstock with a negligible GWP. The present system provides a practical synthetic route to various trifluorovinyl derivatives with very low energy consumption.

Single C–F Transformations of o-Hydrosilyl Benzotrifluorides with Trityl Compounds as All-in-One Reagents

“…Organofluorines are of great significance in a broad range of disciplines such as materials chemistry, pharmaceutical sciences, and chemical biology . In particular, difluoromethylenes are attractive as bioactive compounds and organic materials because of the properties affected by the introduction of fluorine atoms. − In spite of continuous efforts to develop synthetic methods for difluoromethylenes, synthesizing a broad range of difluoromethylenes is still challenging because of the limitation of available building blocks and transformations. − Herein we disclose a practical method for preparing α,α-difluorobenzyl chlorides as versatile organofluorine building blocks. This facile synthesis was achieved by single C–F chlorination of o -hydrosilyl benzotrifluorides with trityl chloride as an all-in-one reagent for generating trityl cation as an activator and chloride anion as a nucleophile.…”

Controllable Fluorocarbon Chain Elongation: TMSCF2Br-Enabled Trifluorovinylation and Pentafluorocyclopropylation of Aldehydes

“…However, all of these established methods mainly focused on the synthesis of fluorine-containing alkenes or cyclopropanes with a single fluorinated carbon atom (C 1 ). Convenient procedures for the synthesis of trifluoroalkenes 11 with two fluorinated carbon atoms (C 2 ) and, in particular, of pentafluorocyclopropanes 12 with three fluorinated carbon atoms (C 3 ) are scarce.…”