2991-99-3Relevant academic research and scientific papers
Transaminases as suitable catalysts for the synthesis of enantiopure β,β-difluoroamines
García-Ramos, Marina,Lavandera, Iván
, 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
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
Difluoromethylation of carboxylic acids via the addition of difluorinated phosphorus ylide to acyl chlorides
Trifonov, Alexey L.,Levin, Vitalij V.,Struchkova, Marina I.,Dilman, Alexander D.
supporting information, p. 5304 - 5307 (2017/11/06)
A one-step protocol for the difluoromethylation of carboxylic acids is described. The reaction involves the interaction of intermediate acyl chlorides with in situ generated difluorinated phosphorus ylide Ph3P=CF2. Aromatic acids can be selectively transformed within one step either to bis-difluoromethylated alcohols or to difluorinated ketones depending on the particular reaction conditions. For bulky α-branched carboxylic acids, only ketones are produced.
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.).
Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o-Alkynylaryl Weinreb Amides
Phetcharawetch, Jongkonporn,Betterley, Nolan M.,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
supporting information, p. 6840 - 6850 (2017/12/26)
[Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride-induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were
One-pot synthesis of difluoromethyl ketones by a difluorination/fragmentation process
Leng, Daniel J.,Black, Conor M.,Pattison, Graham
supporting information, p. 1531 - 1535 (2016/02/10)
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/fragm
In Situ Generated Fluorinated Iminium Salts for Difluoromethylation and Difluoroacetylation
Schmitt, Etienne,Rugeri, Baptiste,Panossian, Armen,Vors, Jean-Pierre,Pazenok, Sergii,Leroux, Frédéric R.
supporting information, p. 4510 - 4513 (2015/09/28)
The use of TFEDMA, a fluoroalkyl amino reagent, for the difluoromethylation and difluoroacylation of arenes, heteroarenes, and C-H acidic compounds is reported. This approach allows for an efficient access to difluoromethylated products of high added valu
Facile preparation of di- and monofluoromethyl ketones from trifluoromethyl ketones via fluorinated enol silyl ethers
Surya Prakash,Hu,Olah
, p. 357 - 362 (2007/10/03)
Di- and monofluoromethyl ketones were prepared from the readily available trifluoromethyl ketones in high yields. Magnesium metal mediated reductive defluorination readily generates fluorinated enol silyl ethers, which upon fluoride or acid assisted hydrolysis give the respective ketones in good to excellent yields.
