Fluoromethylene Transfer from Diarylfluoromethylsulfonium Salts: Synthesis of Fluorinated Epoxides

Chemistry - A European Journal 2019
Jānis Veliks, A. Kazia

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.

Keywords
fluorinated epoxides, fluoromethylenation, fluorooxiranes, Johnson–Corey–Chaykovsky reaction, sulfur fluoromethylylide
DOI
10.1002/chem.201900349
Hyperlink
https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201900349

Veliks, J., Kazia, A. Fluoromethylene Transfer from Diarylfluoromethylsulfonium Salts: Synthesis of Fluorinated Epoxides. Chemistry - A European Journal, 2019, Vol. 25, No. 15, pp.3786-3789. ISSN 0947-6539. Available from: doi:10.1002/chem.201900349

Publication language
English (en)