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

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Abstract

Imine/Oxime-type cobalt complexes, regarded as simple vitamin B12 model 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 V vs. 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 B12 model 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.

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

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Supplementary files

Article information


Submitted
15 Apr 2020
Accepted
18 May 2020
First published
19 May 2020

Dalton Trans., 2020, Advance Article
Article type
Paper

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

L. Cui, T. Ono, Y. Morita and Y. Hisaeda, Dalton Trans., 2020, Advance Article , DOI: 10.1039/D0DT01377C

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