50562-06-6Relevant academic research and scientific papers
Transaminases as suitable catalysts for the synthesis of enantiopure β,β-difluoroamines
García-Ramos, Marina,Lavandera, Iván
supporting information, p. 984 - 988 (2022/02/16)
Transaminases have shown the ability to catalyze the amination of a series of aliphatic and (hetero)aromatic α,α-difluorinated ketones with high stereoselectivity, thus providing the corresponding β,β-difluoroamines in high isolated yields (55–82%) and ex
Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions
Atkins, Alexander P.,Box, John R.,Lennox, Alastair J. J.
, p. 10252 - 10258 (2021/08/12)
CF2H groups are unique due to the combination of their lipophilic and hydrogen bonding properties. The strength of H-bonding is determined by the group to which it is appended. Several functional groups have been explored in this context includ
Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHF2-Containing Trisubstituted Cyclopropanes
Carminati, Daniela M.,Decaens, Jonathan,Couve-Bonnaire, Samuel,Jubault, Philippe,Fasan, Rudi
supporting information, p. 7072 - 7076 (2021/02/27)
The difluoromethyl (CHF2) group has attracted significant attention in drug discovery and development efforts, owing to its ability to serve as fluorinated bioisostere of methyl, hydroxyl, and thiol groups. Herein, we report an efficient biocat
Direct and Chemoselective Synthesis of Tertiary Difluoroketones via Weinreb Amide Homologation with a CHF2-Carbene Equivalent
Miele, Margherita,Citarella, Andrea,Micale, Nicola,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 8261 - 8265 (2019/10/16)
The homologation of Weinreb amides into difluoromethylketones with a formal nucleophilic CHF2 transfer agent is reported. Activating TMSCHF2 with potassium tert-amylate enables a convenient access to the difluorinated homologation re
Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes
Bos, Maxence,Huang, Wei-Sheng,Poisson, Thomas,Pannecoucke, Xavier,Charette, André B.,Jubault, Philippe
supporting information, p. 13319 - 13323 (2017/10/17)
The first catalytic asymmetric synthesis of highly functionalized difluoromethylated cyclopropanes is described. The method, based on a rhodium-catalyzed cyclopropanation of difluoromethylated olefins, gives access to a broad range of cyclopropanes bearing ester, ketone, or nitro functional groups. By using Rh2((S)-BTPCP)4 as a catalyst, the corresponding products were obtained in high yields and high diastereo- and enantioselectivities (up 20:1 d.r. and 99 % ee). This methodology allowed preparation of enantioenriched difluoromethylcyclopropanes for the first time.
Practical Access to Difluoromethyl Ketones via Straightforward Decarboxylative Difluorination of β-Ketoacids
Li, Yin-Long,Li, Jian,Deng, Jun
, p. 1407 - 1412 (2017/04/18)
A facile synthetic approach to a series of difluoromethyl ketones from β-ketoacids has been described. This transformation is achieved through the straightforward decarboxylative difluorination of β-ketoacids in the absence of any catalyst. Furthermore, the resulted difluoromethyl ketones can be easily converted into corresponding difluoromethylated building blocks for pharmaceuticals and materials. (Figure presented.).
Microwave assisted fluorination: an improved method for side chain fluorination of substituted 1-arylethanones
Krane Thvedt, Thor H?kon,Fuglseth, Erik,Sundby, Eirik,Hoff, B?rd Helge
experimental part, p. 9550 - 9556 (2010/02/27)
A two-step, one-pot microwave (MW) assisted fluorination of 1-arylethanones to their corresponding 1-aryl-2-fluoroethanones has been developed. The first step utilises Selectfluor as a fluorinating agent in methanol forming 1-aryl-2-fluoroethanones and their corresponding dimethyl acetals. In the second step, water is added and Selectfluor acts as a Lewis acid in the hydrolytic cleavage of the dimethyl acetals. Compared to the thermal synthesis, the MW assisted method leads to a reduction in reaction time both in the fluorination and for the dimethyl acetal cleavage. Moreover, the one-pot procedure reduces reagent and solvent consumption. The method is best suited for the preparation of 1-aryl-2-fluoroethanones containing substituents that deactivates electrophilic aromatic substitution, however highly electron deficient ketones such as 1-(3,5-dinitrophenyl)ethanone reacts more slowly. Reactions using electron rich aromatic ketones had a low regioselectivity, and also produced fluoroaromatic products.
