Electrochemical Trifluoromethylselenolation of Activated Alkyl Halides. Issue 19 (17th May 2022)

• Record Type: Journal Article
• Authors: Grollier, Kevin; Ghiazza, Clément; Tlili, Anis; Billard, Thierry; Médebielle, Maurice; Vantourout, Julien C.
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 19(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-05-17
• Subjects: Electrochemistry -- Mechanistic investigations -- Method development -- Nucleophilic substitutions -- Trifluoromethylselenolation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200123
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A practical electrochemical method for the generation of CF3 Se − anion from a shelf‐stable reagent (TsSeCF3 ) is reported allowing the metal‐free trifluoromethylselenolation of activated alkyl halides. Trifluoromethylselenolated compounds have been obtained in modest to excellent yields under the optimized reaction conditions. Finally, cyclic voltammetric and 19 F NMR studies are presented and allowed to gain insight into the reaction mechanism. Abstract : A practical electrochemical method for the generation of CF3 Se − anion from a shelf‐stable reagent (TsSeCF3 ) is reported allowing the metal‐free trifluoromethylselenolation of activated alkyl halides. Cyclic voltammetric and 19 F NMR studies are also presented and allowed to gain insight into the reaction mechanism.