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

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.
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Submitted on : Tuesday, February 19, 2019 - 11:10:49 AM
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A. Patra, Fabien Gelat, Xavier Pannecoucke, Thomas Poisson, Tatiana Besset, et al.. Synthesis of 4-Difluoromethylquinolines by NHC-Catalyzed Umpolung of Imines. Organic Letters, American Chemical Society, 2018, 20 (4), pp.1086-1089. ⟨10.1021/acs.orglett.7b04055⟩. ⟨hal-02024525⟩



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