Fluorinated Vinyl Sulfonium Salts and Their Synthetic Utilization

Abstract

The fluorinated building block strategy and the direct fluorination strategy are of great importance for the synthesis of new fluorinated molecules. These strategies complement each other and can be combined to develop a new methodology for the construction of a wide variety of fascinating organofluorine compounds. In our opinion, the versatile building blocks used in this method should satisfy the following conditions: 1) readily prepared from commercially available reagents; 2) easy to handle; 3) storage under ordinary conditions without noticeable decomposition; 4) wide applicability. Based on the aforementioned requirements, we focused on the use of vinyl sulfonium salts. This brief review describes the synthesis of five types of fluorinated vinyl sulfonium salts and their reactions. Especially, we featured typical fluorinated groups containing trifluoromethyl (CF₃ ), difluoromethyl (CF₂ H), monofluoromethyl (CFH₂ ), monofluoro (F) or β-bromotetrafluoroethyl (BrCF₂ CF₂ ) moieties in combination with vinyl sulfonium salts.

Keywords: Fluorinated aziridine; Fluorinated building block; Fluorinated cyclopropane; Vinyl sulfonium salt.