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Article Dans Une Revue Chemistry - A European Journal Année : 2021

Electroreductive cross-coupling of trifluoromethyl alkenes and redox active esters for the synthesis of gem-difluoroalkenes

Clémence Allain

Résumé

An electroreductive access to gem-difluoroalkenes has been developed through the decarboxylative/defluorinative coupling of N-hydroxyphtalimides esters and α-trifluoromethyl alkenes. The electrolysis is performed under very simple reaction conditions in an undivided cell using cheap carbon graphite electrodes. This metal-free transformation features broad scope with good to excellent yields. Tertiary, secondary as well as primary alkyl radicals could be easily introduced. α-aminoacids L-aspartic and L-glutamic acid-derived redox active esters were good reactive partners furnishing potentially relevant gem-difluoroalkenes. In addition, it has been demonstrated that our electrosynthetic approach toward the synthesis of gem-difluoroalkenes could use an easily prepared Kratitsky salt as alkyl radical precursor via a deaminative/defluorinative carbofunctionalization of trifluoromethylstyrene.

Domaines

Chimie organique
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Dates et versions

hal-03452288 , version 1 (26-11-2021)

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Aurélie Claraz, Clémence Allain, Geraldine Masson. Electroreductive cross-coupling of trifluoromethyl alkenes and redox active esters for the synthesis of gem-difluoroalkenes. Chemistry - A European Journal, 2021, ⟨10.1002/chem.202103337⟩. ⟨hal-03452288⟩
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