Journal
DALTON TRANSACTIONS
Volume 49, Issue 22, Pages 7546-7551Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0dt01377c
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Funding
- JSPS KAKENHI [JP17H04875, JP16H06514, JP18H04265, JP19K22204]
- Izumi Science and Technology Foundation
- Nissan Chemical Corporation
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Imine/Oxime-type cobalt complexes, regarded as simple vitamin B(12)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 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 B(12)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.
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