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Issue 79, 2017
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A vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media

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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 RfI (Rf = CF3, n-C3F7, n-C4F9, n-C8F17, and n-C10F21) 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.

Graphical abstract: A vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media

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Publication details

The article was received on 09 Aug 2017, accepted on 12 Sep 2017 and first published on 13 Sep 2017


Article type: Communication
DOI: 10.1039/C7CC06221D
Citation: Chem. Commun., 2017,53, 10878-10881
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    A vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media

    Md. J. Hossain, T. Ono, K. Wakiya and Y. Hisaeda, Chem. Commun., 2017, 53, 10878
    DOI: 10.1039/C7CC06221D

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