Optimized Monofluoromethylsulfonium Reagents for Fluoromethylene-Transfer Chemistry

• DOI: 10.1021/acs.joc.0c02561
• Publication Date: 2021-01-27T17:52:29Z
• Authors: Arturs Sperga; Renate Melngaile; Armands Kazia; Sergey Belyakov; Janis Veliks
• Keywords: Evolutionary Biology; Chemical Sciences not elsewhere classified; fluoromethylene transfer reagents; Immunology; fluorocyclopropanation; Plant Biology; Computational Biology; Optimized Monofluoromethylsulfonium.; monofluorinated cyclopropane deriva.; Biochemistry; 01 natural sciences; 0104 chemical sciences; reactivity; Infectious Diseases; Sociology; Environmental Sciences not elsewhere classified; Genetics; Medicine; aryl ring; fluoromethylene transfer chemistry; Biotechnology; Biological Sciences not elsewhere classified

An investigation of the properties and reactivity of fluoromethylsulfonium salts resulted in the redesign of the reagents for fluoromethylene transfer chemistry. The model reaction, fluorocyclopropanation of nitrostyrene, turned out to be a suitable platform for the discovery of more streamlined fluoromethylene transfer reagents. The incorporation of halides on one aryl ring increased the reactivity, and 2,4-dimethyl substitution on the other aryl ring provided a balance between the reactivity/crystallinity of the reagent as well as the atom economy. The utility of new reagents was demonstrated by the development of an efficient fluorocyclopropanation protocol to access a range of monofluorinated cyclopropane derivatives.