title: Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, The University of Kansas , Lawrence, Kansas 66045, United States.
authors.forename: Yupu
authors.initials: Y
authors.lastname: Qiao
authors.forename: Tuda
authors.initials: T
authors.lastname: Si
authors.forename: Ming-Hsiu
authors.initials: MH
authors.lastname: Yang
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Altman
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D008670:Metals