jo501289v_si_001.pdf (4.63 MB)
Download fileMetal-Free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones
journal contribution
posted on 2015-12-17, 03:30 authored by Yupu Qiao, Tuda Si, Ming-Hsiu Yang, Ryan A. AltmanThe 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.
History
Usage metrics
Categories
Keywords
reaction conditionssequenceTrifluoromethylationAromaticheteroarenebenefitHeteroaromatic Aldehydesconversionmethod featuresKetonesThe abilitymultistepstrategylabor resourcesaldehydeapproachchemistheteroaromatic ketonesaccessingcomplementmaterialheteroarylscalabilityreagentdecarboxylativecompatibilitysubstratefluoroalkyl derivativesrepresentative exampleyieldtransformationstoichiometric metalsarylprocedure