96302-93-1Relevant academic research and scientific papers
Practical Synthesis of α-Trifluoromethylated Pyridines Based on Regioselective Cobalt-Catalyzed [2+2+2] Cycloaddition using Trifluoromethylated Diynes with Nitriles
Kumon, Tatsuya,Yamada, Shigeyuki,Agou, Tomohiro,Fukumoto, Hiroki,Kubota, Toshio,Hammond, Gerald B.,Konno, Tsutomu
supporting information, p. 1912 - 1922 (2021/02/16)
Regioselective cobalt-catalyzed [2+2+2] cycloaddition using fluorine-containing diynes with nitriles was described. Cycloaddition of fluorinated diynes with nitriles under the influence of CoCl2(phen), zinc bromide, and zinc dust in dichloroethane at 80 °C for 3 h took place smoothly, exclusively affording the corresponding α-fluoroalkylated pyridines in excellent yields. In addition, dinitriles as substrate were also found to be suitable for this reaction, giving the corresponding fluoroalkylated bipyridine derivatives in excellent yields. (Figure presented.).
The preparation and cycloaddition reaction of 1-sulfonyl-1-trifluoromethyl allenes
Li, Jun-Li,Yang, Xian-Jin,Jiang, Min,Liu, Jin-Tao
supporting information, p. 3377 - 3379 (2017/08/02)
A series of 1-sulfonyl-1-trifluoromethyl allenes were prepared for the first time from commercial available 2-bromo-3,3,3-trifluoropropene. Cycloaddition reaction of these trifluoromethylated allenes with nitrones occured readily under mild conditions, giving the corresponding trifluoromethylated isoxazolidines in high yields.
A novel synthesis of fluorine-containing cyclopentenones via Pauson-Khand reaction
Konno, Tsutomu,Kida, Takumi,Tani, Akinori,Ishihara, Takashi
, p. 147 - 156 (2013/01/15)
Intermolecular Pauson-Khand reaction of fluoroalkylated alkynes with 2-norbornene or 2,5-norbornadiene at the reflux temperature of dichloroethane proceeded smoothly to give the corresponding cyclopentenone derivatives in high yields as a mixture of regio
Unusual behavior of the anionic species from (E)-1-chloro-3,3,3- trifluoropropene(HCFC-1233t)
Miyagawa, Akiko,Naka, Motoki,Yamazaki, Takashi,Kawasaki-Takasuka, Tomoko
supporting information; experimental part, p. 4395 - 4399 (2010/01/07)
(E)-1-Chloro-3,3,3-trifluoropropene was smoothly deprotonated by MeLi at the position β to the CF3 group, and exclusive formation of propargylic alcohols was observed by addition of appropriate carbonyl compounds as long as up to 1.6 equiv. of
Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes
Shimizu, Masaki,Higashi, Masahiro,Takeda, Youhei,Jiang, Guofang,Murai, Masahito,Hiyama, Tamejiro
, p. 1163 - 1165 (2008/03/13)
A novel method for the generation of 3,3,3-trifluoropropynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-cata
Modified Preparation Method of Trifluoromethylated Propargylic Alcohols and Its Application to Chiral 2,6-Dideoxy-6,6,6-trifluorosugars
Yamazaki, Takashi,Mizutani, Kenji,Kitazume, Tomoya
, p. 6046 - 6056 (2007/10/03)
Convenient generation of 3,3,3-trifluoropropynyl anion was realized from 2-bromo-3,3,3-trifluoropropene, and the anion's reaction with various electrophiles proceeded in excellent isolated yields.One of the products, 1-(benzyloxy)-6,6,6-trifluoro-4-hexyn-3-ol (4b), was further employed for the diastereoselective construction of 2,6-dideoxy-6,6,6-trifluorosugars after enzymatic optical resolution and osmium dihydroxylation of the corresponding olefins.The strongly electron-withdrawing trifluoromethyl moiety, significantly affecting the nucleophilic nature of the neighbouring functionalities, allows to ready differentiation of hydroxy groups by routine chemical transfromation, which results in the shortening of the reaction sequence.
SYNTHESIS AND REACTIVITY OF HEXACARBONYLDICOLBAT COMPLEXES OF TRIFLUOROMETHYLACETYLENE DERIVATIVES
Bobrovnikov, M. N.,Turbanova, E. S.,Shishenin, S. A.,Peterleitner, M. G.,Petrov, A. A.
, p. 1615 - 1626 (2007/10/02)
The lotsich complex formed from 3,3,3-tri-fluoropropyne in ether reacts with acetaldehyde, propionaldehyde, acetone, cyclopentanone, cyclohexanone, and acetophenone to form the corresponding secondary and tertiary trifluoromethylacetylenic alcohols.On reaction with ethylene oxide the secondary alcohol obtained with acetaldehyde is formed in addition to the expected primary alcohol.With octacarbonyldicolbalt the trifluoromethylacetylenic alcohols give the corresponding hexacarbonyldicolbat complexes in high yield.In turn these compounds react with boron trifluoride eth erate forming mixtures of products of intra- and intermolecular dehydration (complexes of trifluoromethylalkenynes, ethers, and ethyl esters) the proportions of which depend on the structure of the alcohol and the reaction conditions.The oxidation potentials of the complexes obtained were 0.5 V higher than for the unfluorinated analogs.The trifluoromethylalkenyne complexes react with ferric nitrate forming the corresponding nitrohydroxy derivatives by adding the elements of nitric acid to the double bond.These are readily dehydrated on silica gel; the hexacarbonyldicobalt fragment is retained.
