Issue 46, 2017

Triple zirconocene/brønsted acid/CuO cooperative and relay catalysis system for tandem Mannich addition/C–C formative cyclization/oxidation

Abstract

A new triple cooperative and relay catalysis system featuring the Mannich addition followed by C–C construction and oxydehydrogenation is described. The zirconocene dichloride and trimellitic acid synergic catalysis triggered the Mannich addition and C–C bond construction reactions, while CuO allowed relay catalysis for oxydehydrogenation. This novel strategy demonstrated superior activity for the synthesis of substituted quinolines from commercially available anilines, aldehydes and ketones. The corresponding substituted quinolines were synthesized with 32 examples in 90–96% yields under mild reaction conditions. A novel zirconocene–Brønsted acid complex, generated in situ and acting as an active catalyst, was validated from the mechanistic studies.

Graphical abstract: Triple zirconocene/brønsted acid/CuO cooperative and relay catalysis system for tandem Mannich addition/C–C formative cyclization/oxidation

Supplementary files

Article information

Article type
Paper
Submitted
20 Jan 2017
Accepted
18 May 2017
First published
31 May 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 28616-28625

Triple zirconocene/brønsted acid/CuO cooperative and relay catalysis system for tandem Mannich addition/C–C formative cyclization/oxidation

Y. Luo, H. Sun, W. Zhang, X. Wang, S. Xu, G. Zhang, Y. Jian and Z. Gao, RSC Adv., 2017, 7, 28616 DOI: 10.1039/C7RA00870H

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