A γ-Fluoro β-Acetoxypropyl Sulfonium Salt as an Equivalent of a (Fluoromethyl)vinyl Sulfonium Salt: Reagent for the Facile Synthesis of Monofluoromethylated Cyclopropanes or Aziridines

Abstract

A β-monofluoromethylated vinyl sulfonium salt, prepared in situ from a precursor γ-fluoro β-acetoxypropyl sulfonium salt under mild basic conditions, reacted with a lvariety of active methylene compounds or a primary sulfone amide under basic conditions to provide the corresponding monofluoromethylated three-membered rings in good-to-excellent yields. This new sulfonium reagent should permit easy access to a variety of important monofluoromethylated organic compounds.

Fluorinated Vinyl Sulfonium Salts and Their Synthetic Utilization

“…Subsequently, a new retrosynthetic protocol for 34 was developed, which has been shown in Scheme 19 [18] . Instead of using similar strategies for the synthesis of 34 , we studied the elimination reaction of the corresponding saturated salts 33 .…”

“…Subsequently, a new retrosynthetic protocol for 34 was developed, which has been shown in Scheme 19. [18] Instead of using similar strategies for the synthesis of 34, we studied the elimination reaction of the corresponding saturated salts 33. Although both precursors 36 and 37 were reported in the literature, we were unable to prepare 37 in our laboratory according to the reported procedure.…”

Divergent synthesis of nitrocyclopropanes and isoxazoline N-oxides from nitro compounds and vinyl sulfonium salts

“…On the other hand, 1,1-bisnucleophiles C such as 1,3-dicarbonyl compounds, cyanoacetates or nitroacetates lead to polysubstituted cyclopropanes E . 4 However, application of substrates bearing one EWG-group such as aliphatic nitro compounds in such transformations is scarcely documented. 5…”

[3 + 2] Cycloaddition Reaction of Vinylsulfonium Salts with Hydrazonoyl Halides: Synthesis of Pyrazoles

“…They usually act as electrophilic Michael acceptors to react with nucleophiles at the β-position to form transient sulfonium ylides and then conduct ylide-initiated tandem reactions, such as annulation, substitution, or elimination reaction, to afford various products (Scheme ). One of their important reaction is the annulation reaction with binucleophiles to afford three- to seven-membered heterocycles in high yields, which provides efficient and valuable strategies for the synthesis of novel bioactive heterocycles (Scheme a) . The second type of reaction of the vinylsulfonium salts is the Johnson–Corey–Chaykovsky-type annulation reaction, which affords fused heterocycles in a single step (Scheme b). , The vinylation of nucleophilic carbon or heteroatom of organic compounds is the third type of reaction of the vinylsulfonium salts (Scheme c) .…”