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Fluoromethylene Transfer from Diarylfluoromethylsulfonium Salts: Synthesis of Fluorinated Epoxides
Author(s) -
Veliks Janis,
Kazia Armands
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900349
Subject(s) - sulfonium , reagent , sulfur , chemistry , combinatorial chemistry , organic chemistry , salt (chemistry)
Abstract Diarylfluoromethyl sulfonium salts are efficient fluoromethylene transfer reagents equivalent to fluorocarbene, which is difficult to access. This was demonstrated by the development of a monofluorinated Johnson–Corey–Chaykovsky reaction with ketones and aldehydes, delivering uncommon 2‐unsubstituted fluoroepoxides. This is the first evidence for the feasibility of sulfur fluoromethylylide and its action as a reaction intermediate.