Patra, Atanu ; Gelat, Fabien ; Pannecoucke, Xavier ; Poisson, Thomas ; Besset, Tatiana ; Biju, Akkattu T. (2018) Synthesis of 4-Difluoromethylquinolines by NHC-Catalyzed Umpolung of Imines Organic Letters, 20 (4). pp. 1086-1089. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.7b04055
Related 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-difluoromethylquinoline 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: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 128632 |
| Deposited On: | 03 Nov 2022 06:48 |
| Last Modified: | 11 Nov 2022 05:47 |
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