α,β-Unsaturated CF3-ketones via secondary amine salts-catalyzed aldol condensation of 1,1,1-trufluoroacetone with aromatic and heteroaromatic aldehydes

•We have developed a facile, expedient and atom-economic method for the synthesis of trifluoromethyl enones and dienones via efficient and chemoselective iminium-catalyzed aldol condensation of trifluoroacetone with aromatic, heteroaromatic and unsaturated aldehydes.•Low catalyst loadings and broad...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2023-04, Vol.267, p.110108, Article 110108
Main Authors: Popov, Alexander V., Kobelevskaya, Valentina A., Borodin, Nikolai I., Zinchenko, Sergey V.
Format: Article
Language:English
Subjects:
Aldehydes, Organocatalysis
Aldol condensation, 1,1,1-trifluoroacetone
Secondary amine salts
Trifluoromethyl enones
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Summary:•We have developed a facile, expedient and atom-economic method for the synthesis of trifluoromethyl enones and dienones via efficient and chemoselective iminium-catalyzed aldol condensation of trifluoroacetone with aromatic, heteroaromatic and unsaturated aldehydes.•Low catalyst loadings and broad substrate scope make this strategy synthetically attractive.•Moreover, such trifluoromethylenones can be obtained on a gram-scale in almost quantitative yields. A facile and efficient approach to the synthesis of α,β-unsaturated CF3-ketones in moderate to excellent yields via the amine salt-catalyzed aldol condensation of aromatic and heteroaromatic aldehydes with trifluoroacetone has been developed. [Display omitted]
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2023.110108