146801-38-9Relevant academic research and scientific papers
Copper-Catalyzed Aldol Reaction of Vinyl Azides with Trifluoromethyl Ketones
Liu, Zhenhua,Zhang, Zhihai,Zhu, Guangyu,Zhou, Yiqin,Yang, Lin,Gao, Wen,Tong, Lili,Tang, Bo
supporting information, p. 7324 - 7328 (2019/10/08)
A novel and efficient aldol reaction of readily available vinyl azides with trifluoromethyl ketones by copper catalysis is developed. The reaction is proposed to go through a nucleophilic trapping of vinyl azides with trifluoromethyl ketones as a trifluor
A Copper-Catalyzed Reductive Defluorination of β-Trifluoromethylated Enones via Oxidative Homocoupling of Grignard Reagents
Wu, Xiaoting,Xie, Fang,Gridnev, Ilya D.,Zhang, Wanbin
supporting information, p. 1638 - 1642 (2018/03/23)
An efficient copper-catalyzed reductive defluorination of β-trifluoromethylated enones via an oxidative homocoupling of Grignard reagents is reported. The reaction proceeded smoothly with a wide range of substrates, including the ones bearing aromatic heterocycles, such as furyl and thienyl ring systems in high yields (80-92%, except one example) under mild conditions. This provides a practical method for synthesis of gem-difluoroolefin ketones. It is also worth noting that this homocoupling process of Grignard reagents using β-trifluoromethylated enones as oxidizing reagents is effective for both the Csp2-Csp2 and Csp3-Csp3 bond formations, including for substrates whose β-hydride elimination of the corresponding transition metal alkyl complex is particularly facile, affording coupling products with high yields (83-95%), simultaneously.
Base-promoted isomerization of CF3-containing allylic alcohols to the corresponding saturated ketones under metal-free conditions
Hamada, Yoko,Kawasaki-Takasuka, Tomoko,Yamazaki, Takashi
, p. 1507 - 1512 (2017/08/14)
Following to the computational expectation, our previously reported intriguing 1,3-proton shift of 4,4,4-trifluorobut-2-yn-1-ols was successfully extended to the 4,4,4-trifluorobut-2-en-1-ol system under metal-free conditions to afford the corresponding saturated ketones in high to excellent chemical yields using such a convenient and easy-to-handle base as DBU at the toluene refluxing temperature, and utilization of the corresponding optically active substrates unambiguously demonstrated that this transformation proceeded in a highly stereoselective fashion.
Catalytic Enantioselective Conjugate Alkynylation of β-Aryl-β-trifluoromethyl Enones Constructing Propargylic All-Carbon Quaternary Stereogenic Centers
Sanz-Marco, Amparo,Blay, Gonzalo,Vila, Carlos,Pedro, José R.
supporting information, p. 3538 - 3541 (2016/08/16)
The enantioselective conjugate alkynylation of β-aryl-β-trifluoromethyl enones has been carried out using terminal alkynes and diethylzinc in the presence of 3,3′-bis(perfluorophenyl)BINOL as the chiral ligand to give the corresponding ketones bearing a t
Efficient and highly enantioselective construction of trifluoromethylated quaternary stereogenic centers via high-pressure mediated organocatalytic conjugate addition of nitromethane to β,β-disubstituted enones
Kwiatkowski, Piotr,Cholewiak, Agnieszka,Kasztelan, Adrian
supporting information, p. 5930 - 5933 (2015/01/09)
A very effective high-pressure-induced acceleration of asymmetric organocatalytic conjugate addition of nitromethane to sterically congested β,β-disubstituted β-CF3 enones has been developed. A combination of pressure (8-10 kbar) and noncovalent catalysis with low-loading of chiral tertiary amine-thioureas (0.5-3 mol %) is shown to provide very efficient access to a wide range of γ-nitroketones containing trifluoromethylated all-carbon quaternary stereogenic centers in the β-position (80-97%, 92-98% ee).
Synthesis of β-CF3 ketones from trifluoromethylated allylic alcohols by ruthenium catalyzed isomerization
Bizet, Vincent,Pannecoucke, Xavier,Renaud, Jean-Luc,Cahard, Dominique
supporting information, p. 56 - 61 (2013/11/06)
This work describes the optimization process for the synthesis of β-trifluoromethylated ketones from trifluoromethylated allylic alcohols. This transformation proceeds through a ruthenium catalyzed isomerization under mild conditions with high atom econom
Ruthenium-catalyzed redox isomerization of trifluoromethylated allylic alcohols: Mechanistic evidence for an enantiospecific pathway
Bizet, Vincent,Pannecoucke, Xavier,Renaud, Jean-Luc,Cahard, Dominique
supporting information; experimental part, p. 6467 - 6470 (2012/07/27)
Transfer news: A synthetic approach to chiral β-CF3- substituted saturated carbonyl compounds has been developed in which ruthenium complexes efficiently catalyze the redox isomerization of CF3-bearing allylic alcohols by an intramol
A newly-designed PE-supported arsine for efficient and practical catalytic Wittig olefination
Wang, Peng,Liu, Chun-Rong,Sun, Xiu-Li,Chen, Shuai-Shuai,Li, Jun-Fang,Xie, Zuowei,Tang, Yong
supporting information; experimental part, p. 290 - 292 (2012/01/06)
A newly designed PE-supported arsine has been developed as an excellent catalyst for catalytic Wittig-type olefination. Simple ketones, in particular inactive ketones prove to be suitable substrates for the first time. This reaction provides an easy access to di-, tri-, and tetra-substituted olefins in high yield.
Enantioselective synthesis of trifluoromethyl-substituted 2-isoxazolines: Asymmetric hydroxylamine/enone cascade reaction
Matoba, Kazutaka,Kawai, Hiroyuki,Furukawa, Tatsuya,Kusuda, Akihiro,Tokunaga, Etsuko,Nakamura, Shuichi,Shiro, Motoo,Shibata, Norio
supporting information; experimental part, p. 5762 - 5766 (2010/11/03)
(Figure Presented) Cuts both ways: The title reaction consists of an addition/cyclization/dehydration sequence and affords the biologically important chiral 3,5-diaryl-5-(trifluoromethyl)-2-isoxazolines 1 in excellent yields with high ee values. The flexi
Palladium-catalyzed regio- and stereoselective formate reduction of fluorine-containing allylic mesylates. A new entry for the construction of a tertiary carbon attached with a fluoroalkyl group
Konno, Tsutomu,Takehana, Tsuyoshi,Mishima, Makoto,Ishihara, Takashi
, p. 3545 - 3550 (2007/10/03)
The regioselective palladium-catalyzed formate reduction of γ-fluoroalkylated allylic esters is described. Reduction of the allylic esters under the influence of palladium with a monodentate phosphine ligand proceeded preferentially at the γ position, the corresponding reduction products with a fluoroalkyl group at the tertiary carbon being afforded in high yields. When the chiral allylic ester was employed, complete chirality transfer was observed, leading to the optically active materials in high yields.
