Metal-Free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones
journal contributionposted on 2015-12-17, 03:30 authored by Yupu Qiao, Tuda Si, Ming-Hsiu Yang, Ryan A. Altman
The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl β,β,β-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction sequences that consume excessive time, material, and labor resources while providing low yields of products. To complement these traditional strategies, we report a one-pot metal-free decarboxylative procedure for accessing β,β,β-trifluoroethylarenes and -heteroarenes from readily available ketones and aldehydes. This method features several benefits, including ease of operation, readily available reagents, mild reaction conditions, high functional-group compatibility, and scalability.
reaction conditionssequenceTrifluoromethylationAromaticheteroarenebenefitHeteroaromatic Aldehydesconversionmethod featuresKetonesThe abilitymultistepstrategylabor resourcesaldehydeapproachchemistheteroaromatic ketonesaccessingcomplementmaterialheteroarylscalabilityreagentdecarboxylativecompatibilitysubstratefluoroalkyl derivativesrepresentative exampleyieldtransformationstoichiometric metalsarylprocedure