80020-16-2Relevant academic research and scientific papers
Base Catalysis Enables Access to α,α-Difluoroalkylthioethers
Orsi, Douglas L.,Easley, Brandon J.,Lick, Ashley M.,Altman, Ryan A.
, p. 1570 - 1573 (2017)
A nucleophilic addition reaction of aryl thiols to readily available β,β-difluorostyrenes provides α,α-difluoroalkylthioethers. The reaction proceeds through an unstable anionic intermediate, prone to eliminate fluoride and generate α-fluorovinylthioethers. However, the use of base catalysis overcomes the facile β-fluoride elimination, generating α,α-difluoroalkylthioethers in excellent yields and selectivities.
Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones
Qiao, Yupu,Si, Tuda,Yang, Ming-Hsiu,Altman, Ryan A.
, p. 7122 - 7131 (2014/08/18)
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.
