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Green Chemistry

IF: 9.3
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Electrochemical oxidative cross-coupling of tetrahydroquinolines and azoles?

Published:7 May 2024 DOI: 10.1039/d3gc04453j
Dan Yang , Yu-Fang Tan , Ya-Nan Zhao , Jin-Feng Lv , Zhi Guan , Yan-Hong He

Abstract

A novel electrochemical method is described for the direct oxidative C–N coupling of tetrahydroquinolines and azoles, enabling the synthesis of dihydroquinoline derivatives under mild reaction conditions. In this approach, 2,2,6,6-tetramethylpiperidinooxy (TEMPO) serves as a redox mediator, and NaI not only acts as an electrolyte but also functions as an iodine mediator. The reaction exhibits good functional group tolerance and high atomic economy, resulting in moderate to excellent yields of the desired dihydroquinoline derivatives. Furthermore, by adjusting the reaction conditions, the corresponding quinoline derivatives can also be selectively obtained.

Substances (4)

Related products
Procduct Name CAS Molecular Formula Supplier Price
TEMPO 2564-83-2 C9H18NO* 658 suppliers $6.00-$2433.70
1-Acetylimidazole 2466-76-4 C5H6N2O 413 suppliers $13.00-$1250.00
AZO BLUE 6059-34-3 C34H24N4Na2O8S2 34 suppliers $16.00-$1231.00
2,6-dichloro-8-methyl-5-nitro-1,4-dihydroquinoline 1082726-51-9 - Inquiry

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