A vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media. Issue 79 (20th September 2017)

• Record Type: Journal Article
• Authors: Hossain, Md. Jakir; Ono, Toshikazu; Wakiya, Kosuke; Hisaeda, Yoshio
• Is Part Of: Chemical communications. Volume 53:Issue 79(2017)
• Page Start: 10878
• Page End: 10881
• Publication Date: 2017-09-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc06221d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The electrochemical trifluoromethylation and perfluoroalkylation of aromatic compounds mediated by a vitamin B12 derivative as a cobalt-based catalyst has been developed. Abstract : The electrochemical trifluoromethylation and perfluoroalkylation of aromatic compounds mediated by a vitamin B12 derivative as a cobalt-based catalyst has been developed. The Co(i ) species of a vitamin B12 derivative, prepared by controlled-potential electrolysis at −0.8 V vs. Ag/AgCl in methanol, reacted with Rf I (Rf = CF3, n -C3 F7, n -C4 F9, n -C8 F17, and n -C10 F21 ) to form a Co–Rf complex. This complex released an Rf radical under visible light irradiation, which then reacted directly with non-activated (hetero)arenes to form the desired fluoroalkylated molecules through direct C–H functionalization. To our knowledge, this is the first report of a naturally derived vitamin B12 catalyzed trifluoromethylation and perfluoroalkylation of aromatic compounds as a cobalt-mediated catalyst.