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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

Research paper by Fujiwara, Yuuri, Muta, Ryuhei, Sato, Keiichi, Haramura, Hiroaki, Yamada, Yasunori, Hanamoto, Takeshi

Indexed on: 05 Oct '18Published on: 30 Sep '18Published in: Synlett : accounts and rapid communications in synthetic organic chemistry



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.