Synthesis and Applications of Fluorine(s)-Containing Vinyl Sulfonium Salts

Hanamoto Takeshi

doi:10.5059/yukigoseikyokaishi.76.710

<p>The introduction of fluorine(s) into organic compounds can change physical, chemical, and biological properties of their original molecules. In the context, the trifluoromethyl group (CF₃) is probably the most popular; it is also most applied in the design and development of drugs, agrochemicals, and material science. The development of effective and efficient synthetic approaches to access such trifluoromethylated molecules has gained great attention. Although the direct trifluoromethylation method using various trifluoromethylating reagents appears to be the latest trends, such reagents are ordinarily expensive. On the other hand, the use of trifluoromethylated building blocks represents an alternative approach provided that the trifluoromethylated building blocks are satisfied the following conditions: 1) easy to prepare from commercially available reagents 2) easy to handle 3) wide application ability. Our group has been interested in the preparation of fluorinated building blocks containing vinyl sulfonium group as a key functional group. On the basis of the above concept, so far, β-(trifluoromethyl)vinyl sulfonium salt, β-(difluoromethyl)vinyl sulfonium salt, and α-fluorovinyl sulfonium salt have already synthesized from readily available starting materials in high overall yields in short steps. These salts have functioned as a two-carbon homologation reagent containing trifluoromethyl, difluoromethyl, and monofluoro moiety. In this article, we will discuss synthesis and application of the fluorinated vinyl sulfonium salts and related compounds.</p>

Synthesis and Applications of Fluorine(s)-Containing Vinyl Sulfonium Salts

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