78622-58-9Relevant academic research and scientific papers
Synthesis of CF3-substituted olefins by julia-kocienski olefination using 2-[(2,2,2-Trifluoroethyl)sulfonyl]benzo[d]thiazole as trifluoromethylation agent
Hafner, Andreas,Fischer, Tobias S.,Braese, Stefan
, p. 7996 - 8003 (2013)
A modified Julia-Kocienski protocol was investigated for the synthesis of CF3-substituted terminal olefins. By employing a simple one-step procedure, aldehydes were converted into the corresponding CF 3-substituted olefins using 2-[(2,2,2-trifluoroethyl)sulfonyl] benzo[d]thiazole as the trifluoromethylation agent. This sulfone was prepared on a gram scale in two steps from inexpensive and commercially available trifluoroethanol. The Julia-Kocienski olefination tolerated various functional groups, and the trifluoromethylated olefins were obtained in good yields. However, the E/Z selectivity was strongly substrate dependent, and only moderate selectivities could be achieved. By employing a two-step procedure, it was possible to synthesize an α-trifluoromethyl-substituted sulfone on a gram scale by starting from inexpensive and commercially available trifluoroethanol. This substrate could then be used in a modified Julia-Kocienski olefination to prepare trifluoromethyl-substituted terminal olefins). Copyright
Metal-Free Visible-Light-Mediated Hydrotrifluoromethylation of Unactivated Alkenes and Alkynes in Continuous Flow
Barthelemy, Anne-Laure,Dagousset, Guillaume,Magnier, Emmanuel
supporting information, p. 1429 - 1432 (2019/11/13)
We report herein a novel photoredox-catalyzed hydrotrifluoromethylation of unsaturated systems under continuous flow. This metal-free method is easily broadened to other perfluoroalkyl groups (RF = CF3, CFCl2, CF2/su
Phosphine-Relayed Aldehyde-Olefination and Aza-Wittig Reaction with 2,2,2-Trifluorodiazoethane
Zhang, Fa-Guang,Lv, Ning,Zheng, Yan,Ma, Jun-An
, p. 723 - 730 (2018/07/29)
Phosphine-relayed olefination and aza-Wittig reactions of readily available aldehydes with 2,2,2-trifluorodiazoethane (CF3CHN2) have been realized. This protocol enables the facile construction of a series of trifluoromethylated alkenes and hydrazones in good to high yield under mild conditions.
MONOSUBSTITUTED(FLUOROALKYL)ETHYLENES AND METHOD OF PRODUCING THE SAME
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Paragraph 0092; 0093, (2017/01/02)
PROBLEM TO BE SOLVED: To provide a method of efficiently producing monosubstituted(fluoroalkyl)ethylenes. SOLUTION: The method comprises reacting a 1-chloro-2-(fluoroalkyl)ethylene with an organoboron compound under coexistence of an alkylphosphine coordinated palladium catalyst, an alkali metal salt and water so as to obtain a monosubstituted(fluoroalkyl)ethylene represented by the general formula (5). (In the formula, R represents a naphthalene-1-yl group or the like, and Rf represents C1-4 fluoroalkyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
Julia-Kocienski approach to trifluoromethyl-substituted alkenes
Ayeni, Deborah O.,Mandal, Samir K.,Zajc, Barbara
supporting information, p. 6008 - 6011 (2013/10/22)
A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach.
Highly selective activation of vinyl C-S bonds over aryl C-S bonds in the Pd-catalyzed coupling of (E)-(β-trifluoromethyl)vinyldiphenylsulfonium salts: Preparation of trifluoromethylated alkenes and dienes
Lin, Hao,Dong, Xicheng,Li, Yuxue,Shen, Qilong,Lu, Long
supporting information; experimental part, p. 4675 - 4679 (2012/10/08)
We describe the Suzuki coupling reaction of (E)-(β-trifluoromethyl) vinyldiphenylsulfonium salts with arylboronic acid. The highly efficient and selective reaction provides a useful and mild method for the synthesis of trifluoromethylated alkenes and dienes. Subsequent DFT studies showed that the oxidative addition transition state of the vinyl C-S bond is much more favorable (11.7 kcal mol-1) than that of the aryl C-S bond. Copyright
Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
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Page/Page column 32, (2008/06/13)
Compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.
Convenient synthesis of 3,3,3-trifluoropropenyl compounds from aromatic aldehydes by means of the TBAF-mediated horner reaction
Kobayashi, Tetsuya,Eda, Takuya,Tamura, Osamu,Ishibashi, Hiroyuki
, p. 3156 - 3159 (2007/10/03)
A simple synthesis of 3,3,3-trifluoropropenyl compounds by means of the TBAF-mediated Horner reaction is described. The reagent, 2,2,2-trifluoroethyldiphenylphosphine oxide, was readily prepared either by Arbuzov reaction of ethyl diphenylphosphinite with 2,2,2-trifluoroethyl iodide or by treating chlorodiphenylphosphine with trifluoroacetic acid and water. Treatment of the phosphine oxide with aromatic aldehydes in the presence of TBAF at room temperature afforded the corresponding 3,3,3-trifluoropropenyl compounds in good yields. The present method is very convenient for preparing 3,3,3-trifluoropropenyl compounds from aromatic aldehydes in terms of availability of the reagent, operational simplicity, and good yields of the products.
