Electrocatalytic reactivity of imine/oxime-type cobalt complex for direct perfluoroalkylation of indole and aniline derivatives

Luxia Cui, Toshikazu Ono, Yoshitsugu Morita, Yoshio Hisaeda

Research output: Contribution to journalArticle

Abstract

Imine/Oxime-type cobalt complexes, regarded as simple vitamin B12model complexes, were utilized as catalysts for direct C-H perfluoroalkylations of indole and aniline derivatives with nonafluorobutyl iodide (n-C4F9I) as the readily available perfluoroalkyl source. The synthetic approach described herein was performed under mild reaction conditions driven by controlled-potential electrolysis at −0.8 Vvs.Ag/AgCl in organic solvents. The mechanistic investigations suggest that a nonafluorobutyl radical is mediated by homolytic cleavage of the cobalt(iii)-carbon bond in the catalytic cycle. This is the first report concerning a fluoroalkylation reaction of (hetero)aromatics catalyzed by the simple vitamin B12model complex. The convenient electrocatalytic method employing a simple cobalt complex provides a facile synthesis method toward novel fluoroalkylated compounds, demonstrating potential applications in the fields of pharmaceutical chemistry and materials science.

Original languageEnglish
Pages (from-to)7546-7551
Number of pages6
JournalDalton Transactions
Volume49
Issue number22
DOIs
Publication statusPublished - Jun 14 2020

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

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