Difluoromethyl ketones are an under-studied class of ketones which have great potential as useful building blocks for materials and drug design. Here we report a simple and convenient synthesis of this class of compounds via a one-pot difluorination/fragmentation of 1-trifluoromethyl-1,3-diketones which should now allow the chemistry of difluoromethyl ketones to be fully developed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c5ob02468d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Mechanochemical difluoromethylations of ketones.
Beilstein J Org Chem
November 2024
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.
We present a mechanochemical synthesis of difluoromethyl enol ethers. Utilizing an in situ generation of difluorocarbenes, ketones are efficiently converted to the target products under solvent-free conditions. The reactions proceed at room temperature and are complete within 90 minutes, demonstrating both efficiency and experimental simplicity.
View Article and Find Full Text PDFA Continuous Flow Process for the Defluorosilylation of HFC-23 and HFO-1234yf.
Org Lett
October 2024
Department of Chemistry, Molecular Sciences Research Hub, 82 Wood Lane, Shepherds Bush, London, W12 0BZ, U.K.
A continuous flow process has been developed for the defluorosilylation of trifluoromethane (HFC-23) and 2,3,3,3-tetrafluoropropene (HFO-1234yf) through reaction with lithium silanide reagents under inert conditions. Design of experiment optimization improved process conditions, including productivity, yields, reduction of solvent use, and gas destruction. The small chain fluorinated organosilane products RSiCFH and RSiCHC(F)═CF were competent nucleophiles in the fluoride-catalyzed difluoromethylation of aldehydes, and trifluoroallylation of aldehydes, ketones, and imines.
View Article and Find Full Text PDFStability studies of β-Amino- and β-Hydroxy difluoromethyl ketones in rat serum and rat liver microsomes.
Bioorg Med Chem Lett
November 2024
Department of BioMolecular Sciences, University of Mississippi, University, MS 38677, USA. Electronic address:
Although difluoromethyl ketones are used as tools in chemical biology and leads in drug discovery, the metabolic stability of these compounds is generally uncharacterized and must be inferred from in vivo pharmacological assays. In order to address this gap which impedes their wider use, we have synthesized and performed metabolic stability studies for thirty-nine β-amino and β-hydroxy difluoromethyl ketones. These investigations provide structure-stability relationships of the difluoromethyl ketones following incubation with rodent serum and liver microsomes.
View Article and Find Full Text PDFChemoselective Synthesis of α-Halo--difluoromethyl Ketones from Trimethyl(phenylethynyl)silane.
Org Lett
May 2024
School of Environmental and Chemical Engineering, Wuyi University, Jiangmen 529020, P. R. China.
Here, we describe a novel strategy for chemoselective synthesis of α-halo--difluoromethyl ketones (-COCF and -COClCF motifs) from trimethyl(phenylethynyl)silane under catalyst-free and mild conditions. Commercially available Selectfluor or additional NaCl as halogen reagent was employed to complete this transformation, thereby demonstrating the potential synthetic value of this new reaction in organic synthesis.
View Article and Find Full Text PDFSemipinacol Rearrangement of Iododifluorohomoallyl Alcohols and Its Application in the Allylic C-H Esterification Reactions.
J Org Chem
March 2024
Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
We herein present a study on the Ag(I)-mediated semipinacol rearrangement of iododifluorohomoallyl alcohols, the resulting allylic difluoromethyl ketones underwent oxidative allylic C-H esterification under palladium catalysis in the absence of external ligand. This process yielded a range of difluoromethyl ketones derived from allyl esters in a single operation. The reaction features broad scope of -nitrobenzoic acids and homoallylic iododifluoroalcohols affording the targeted molecules in synthetically useful yields.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!