American Chemical Society
jo501289v_si_001.pdf (4.63 MB)

Metal-Free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones

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journal contribution
posted 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.