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Synthesis of 4-Difluoromethylquinolines by NHC-Catalyzed Umpolung of Imines

Patra, Atanu and Gelat, Fabien and Pannecoucke, Xavier and Poisson, Thomas and Besset, Tatiana and Biju, Akkattu T (2018) Synthesis of 4-Difluoromethylquinolines by NHC-Catalyzed Umpolung of Imines. In: ORGANIC LETTERS, 20 (4). pp. 1086-1089.

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Official URL: http://dx.doi.org/10.1021/acs.orglett.7b04055

Abstract

The N-heterocyclic carbene (NHC)-catalyzed umpolung of aldimines for the synthesis of 4-difluoromethyl-quinoline derivatives is reported. In the presence of NHCs, the intramolecular cyclization of aldimines bearing a moderately electron-poor double bond due to the presence of the -CF3 group likely proceeds via the intermediacy of the aza-Breslow intermediate. The key to the success of this aza-Stetter type transformation is the NHC generated from the bicyclic triazolium salt using DBU as the base.

Item Type: Journal Article
Additional Information: Copy right for the article belong to AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 19 Mar 2018 18:28
Last Modified: 19 Mar 2018 18:28
URI: http://eprints.iisc.ac.in/id/eprint/59247

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