655-54-9Relevant articles and documents
Practical Access to Difluoromethyl Ketones via Straightforward Decarboxylative Difluorination of β-Ketoacids
Li, Yin-Long,Li, Jian,Deng, Jun
, p. 1407 - 1412 (2017)
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.).
A Carbene Strategy for Progressive (Deutero)Hydrodefluorination of Fluoroalkyl Ketones
Bi, Xihe,Sivaguru, Paramasivam,Song, Qingmin,Wang, Zikun,Zanoni, Giuseppe,Zhang, Xiaolong,Zhang, Xinyu
supporting information, (2021/12/23)
Hydrodefluorination is one of the most promising chemical strategies to degrade perfluorochemicals into partially fluorinated compounds. However, controlled progressive hydrodefluorination remains a significant challenge, owing to the decrease in the stre
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
Decarboxylative nucleophilic difluoromethylation of aldehydes and imines
Chen, Jia,Lin, Jin-Hong,Xiao, Ji-Chang
supporting information, p. 4295 - 4297 (2018/07/13)
The high demand for the biologically active CF2H-molecules has stimulated significant efforts to develop efficient methods for the installation of CF2H functionality. We found that phenylsulfonyl difluoroacetate salt (PhSO2/sub
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.
Conversion of methyl ketones and methyl sulfones into α-deutero-α,α-difluoromethyl ketones and α-deutero-α,α-difluoromethyl sulfones in three synthetic steps
Sowaileh, Munia F.,Han, Changho,Hazlitt, Robert A.,Kim, Eun Hoo,John, Jinu P.,Colby, David A.
supporting information, p. 396 - 400 (2017/01/10)
Deuterodifluoromethyl ketones and sulfones were assembled in three synthetic steps from methyl ketones and sulfones, respectively. The key synthetic transformation is the deuteration of the difluorocarbanion generated by the release of trifluoroacetate from highly α-fluorinated gem-diols. High levels of deuterium on the “CF2D” group were routinely observed. This strategy is mild and versatile and it can be applied to both ketones and sulfones without additional concerns of over- or under-fluorination. Additional examples address issues of over-deuteration when compounds with other acidic protons are subjected to the reaction conditions. This process not only demonstrates a new method to install a “CF2D” group but also extends the scope of trifluoroacetate release to sulfones.
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
Nucleophilic Iododifluoromethylation of Aldehydes Using Bromine/Iodine Exchange
Levin, Vitalij V.,Smirnov, Vladimir O.,Struchkova, Marina I.,Dilman, Alexander D.
, p. 9349 - 9353 (2015/09/28)
A method for the iododifluoromethylation of aromatic aldehydes using (bromodifluoromethyl)trimethylsilane (Me3SiCF2Br) is described. The selective formation of the CF2I group is based on using sodium iodide, with the sodium serving as a scavenger of bromide and iodide serving as a nucleophile with respect to difluorocarbene. The primary CF2I-addition products can undergo HI-elimination or iodine/zinc exchange followed by allylation in a one-pot manner.
