1314603-83-2Relevant academic research and scientific papers
Visible light induced Trifluoromethyl Migration: Easy Access to α-Trifluoromethylated Ketones from Enol Triflates
Liu, Shuyang,Jie, Jiyang,Yu, Jipan,Yang, Xiaobo
, p. 267 - 271 (2018)
Herein, we reported a novel method to synthesize α-trifluoromethylated ketones from enol triflates. Involving a cascade sulfur dioxide extrusion and a CF3 (trifluoromethyl) radical addition process, this reaction proceeds at room temperature an
Scissoring Enaminone C=C Double Bond by Free Radical Process for the Synthesis of α-Trifluoromethyl Ketones with CF3SO2Na
Gan, Lu,Yu, Qing,Liu, Yunyun,Wan, Jie-Ping
, p. 1231 - 1237 (2020/12/21)
The C=C double bond cleavage on tertiary enaminones, enabling the formation of a new C-CF3 bond, has been realized as a practical method for the synthesis of α-trifluoromethyl ketones with only the promotion of TBHP and ambient heating. Control experiments support that the reactions proceed via a featured free radical process. The deuterium labeling experiment employing D2O indicates that water participated in the product formation by donating the hydrogen atom for the newly generated α-C-H bond in the product.
METHOD FOR PRODUCING α-FLUOROALKYL KETONE AND β-FLUOROALKYL ALCOHOL
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Paragraph 0073-0075, (2020/07/03)
PROBLEM TO BE SOLVED: To provide a method for producing α-fluoroalkyl ketone and β-fluoroalkyl alcohol conveniently, inexpensively and efficiently. SOLUTION: A method for producing α-fluoroalkyl ketone represented by formula (II) (where Rf is a fluoroalkyl group) includes reacting an alkyne compound represented by formula (I) (where R1 is a chain hydrocarbon group, cyclic aliphatic hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, -OR3, -NR4R4', R2 is a hydrogen atom, trialkylsilyl group, diallyl alkylsilyl group, or triallylsilyl group), in the presence of a radical initiator, with a fluoroalkyl sulfonic acid. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
A Concise and Efficient Approach to 2,6-Disubstituted 4-Fluoro pyrimidines from α-CF 3 Aryl Ketones
Liu, Fangran,Qian, Qun,Yang, Chunhao,Zhang, Xiaofei
supporting information, p. 273 - 280 (2019/12/28)
Herein, a concise and efficient protocol to synthesize a series of 2,6-disubstituted 4-fluoropyrimidines as universal and useful building blocks in medicinal chemistry is reported. From readily accessible α-CF 3 aryl ketones and different amidine hydrochlorides, this method provides a very practical approach to this kind of compounds under mild conditions with good to excellent yields.
Photooxidative Keto-Trifluoromethylation of Styrenes by Means of an Anthraquinone-Based Organocatalyst
Yamaguchi, Eiji,Kamito, Yuji,Matsuo, Kazuki,Ishihara, Jun,Itoh, Akichika
, p. 3161 - 3168 (2018/05/25)
α-Trifluoromethyl ketones are versatile building blocks for the synthesis of various trifluoromethyl-functionalized molecules. Although there are significant advantages in the development of methods toward direct transformations of styrenes into α-trifluoromethyl ketones, most procedures leading to α-trifluoromethyl ketones require heavy- or transition-metal-based complexes. Herein, a novel method is developed for the synthesis of α-trifluoromethyl ketones via anthraquinone-catalyzed photooxidative keto-trifluoromethylation of styrenes with the readily available Langlois reagent (CF 3 SO 2 Na) under an oxygen atmosphere. The reactions proceed smoothly to give the products in moderate to excellent yield with good selectivity.
Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to α-Trifluoromethyl Ketones
Su, Xiaolong,Huang, Honggui,Yuan, Yaofeng,Li, Yi
supporting information, p. 1338 - 1341 (2017/01/24)
We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of α-CF3ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3radical fr
Alpha-trifluoromethyl ketone compounds and preparation method thereof
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Paragraph 0042; 0043; 0044, (2018/04/01)
The invention discloses a preparation method of alpha-trifluoromethyl ketone compounds and the compounds. A series of alpha-trifluoromethyl ketone compounds containing various functional groups are synthesized under conditions of room temperature and illumination. The preparation method of the alpha-trifluoromethyl ketone compounds and the compounds have the following advantages: operation is simple, raw materials are cheap and available, an application range of substrates is wide, most substrates are high in yield, and harsh reaction conditions are avoided.
Oxidative trifluoromethylation and fluoroolefination of unactivated olefins
Wu, Ye-Bin,Lu, Guo-Ping,Yuan, Tao,Xu, Zhu-Bing,Wan, Li,Cai, Chun
, p. 13668 - 13670 (2016/11/29)
Fluorine-containing organic compounds are gaining increasing importance in medicinal chemistry. Described herein is a mild and efficient method for the radical addition of olefins with TMSCF3 and TMSCF2R (R = COOEt or CF3) to deliver various α-trifluoromethylated ketones and α-fluoroolefinated ketones.
Activation of Trifluoromethylthio Moiety by Appending Iodonium Ylide under Copper Catalysis for Electrophilic Trifluoromethylation Reaction
Saidalimu, Ibrayim,Suzuki, Shugo,Tokunaga, Etsuko,Shibata, Norio
supporting information, p. 485 - 489 (2016/05/24)
A novel iodonium-ylide compound 2 that appends atrifluoromethylthio (SCF3) group is disclosed as a new, shelf-stable electrophilic trifluoromethylation reagent. Unlike known shelf-stable electrophilic trifluoromethylation reagents, 2 has a stable SCF3 group which is activated by appending iodonium ylide under copper catalysis via sulfonium ylide to generate a cationic trifluoromethyl (CF3) species. Reagent 2 was found to be an efficient electrophilic trifluoromethylation reagent for a wide range of silyl enol ethers 3 under copper catalysis. Cyclic and acyclic α-trifluoromethyl ketones 4 were obtained by reagent 2 in moderate to good yields. On the other hand, a difluoromethylthio analogue 5 did not affect intermolecular transfer difluoromethylation to substrates. Instead, intramolecular 1,4-migration proceeded similar to the Stevens rearrangement to provide 6 in 21% yield, independent of the presence of nucleophiles 3.
Direct synthesis of α-trifluoromethyl ketone from (hetero)arylacetylene: Design, intermediate trapping, and mechanistic investigations
Maji, Arun,Hazra, Avijit,Maiti, Debabrata
supporting information, p. 4524 - 4527 (2015/01/09)
Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O2 to access medicinally active α-trifluoromethyl ketone compounds. This metho
