A Vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media

Md Jakir Hossain, Toshikazu Ono, Kosuke Wakiya, Yoshio Hisaeda

Research output: Contribution to journalArticle

13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)10878-10881
Number of pages4
JournalChemical Communications
Volume53
Issue number79
DOIs
Publication statusPublished - Jan 1 2017

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Vitamins
Vitamin B 12
Aromatic compounds
Cobalt
Derivatives
Catalysts
Electrolysis
Methanol
Irradiation
Molecules

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

A Vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media. / Hossain, Md Jakir; Ono, Toshikazu; Wakiya, Kosuke; Hisaeda, Yoshio.

In: Chemical Communications, Vol. 53, No. 79, 01.01.2017, p. 10878-10881.

Research output: Contribution to journalArticle

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