3108-34-7Relevant academic research and scientific papers
Oxidation of 4-Aryl-1,1,1-trifluorobut-2-en-2-yl Trifluoro?-methanesulfonates by 4-Picoline-N-Oxide: A Novel Approach to β-Trifluoromethyl-α,β-enones
Li, Dong,Lv, Shujun,Qu, Jingping,Zhou, Yuhan
, p. 1203 - 1210 (2020/04/15)
An efficient approach to β-trifluoromethyl-α,β-enones via oxidation of 4-aryl-1,1,1-trifluorobut-2-en-2-yl trifluoromethanesulfonates is described. The reaction proceeds smoothly under mild and metal?-free conditions and tolerates a wide range of functional groups. Various β-trifluoromethyl-α,β-enones were obtained in moderate to good yields.
Preparation method of (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound
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Paragraph 0054-0056; 0108-0173, (2020/03/02)
The invention discloses a preparation method of an (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound, and belongs to the field of compound preparation. The (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound is prepared by taking a compound shown
Highly Enantioselective [3 + 2] Annulation of 3-Butynoates with β-Trifluoromethyl Enones Promoted by an Amine-Phosphine Binary Catalytic System
Ding, Kuiling,Han, Zhaobin,Lu, Yixin,Ni, Huanzhen,Wong, Yee Lin,Wu, Mingyue
, (2020/03/30)
We report a highly enantioselective [3 + 2] annulation between 3-butynoates and β-trifluoromethyl enones, furnishing trifluoromethylated cyclopentenes with three contiguous stereogenic centers in good yields, high diastereoselectivities, and excellent enantioselectivities. A unique catalytic system consisting of a simple amine and a chiral phosphine was devised, and the synergistic play of Lewis basic amine and phosphine was crucial for alkyne isomerization and subsequent cyclization. The protocol disclosed herein allows facile activation of 3-butynoates in phosphine-mediated asymmetric transformations.
Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao
supporting information, p. 5040 - 5045 (2019/07/03)
(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones
Ramasamy, Manickavasakam,Lin, Hui-Chang,Kuo, Sheng-Chu,Hsieh, Min-Tsang
, p. 356 - 360 (2019/02/12)
A practical Lewis acid-catalyzed Meyer-Schuster rearrangement of fluoroalkylated propargylic alcohols, leading to a series of β-fluoroalkyl-α,β-enones, is developed. The methodology reported herein features moderate to high yields and high stereoselectivi
Rh(III)-Catalyzed [3 + 2] Annulation via C-H Activation: Direct Access to Trifluoromethyl-Substituted Indenamines and Aminoindanes
Chaudhary, Bharatkumar,Auti, Prashant,Shinde, Suchita Dattatray,Yakkala, Prasanna Anjaneyulu,Giri, Deepesh,Sharma, Satyasheel
supporting information, p. 2763 - 2767 (2019/04/30)
The rhodium(III)-catalyzed direct C-H addition and annulation of benzimidates and aldimines with β-(trifluoromethyl)-α,β-unsaturated ketones is described. This protocol provides the facile and efficient formation of various trifluoromethyl-containing inde
A Remarkable Influence of a Trifluoromethyl Group on the Reactions of β-Mercaptoalcohols with Fluorinated α-Bromoenones
Obijalska, Emilia,Pawelec, Maria,Mlostoń, Grzegorz,Capperucci, Antonella,Tanini, Damiano,Heimgartner, Heinz
, p. 3716 - 3723 (2018/04/09)
Isomeric fluorinated α-bromoenones react with dinucleophilic β-mercaptoalcohols in CH2Cl2 at room temperature in the presence of Et3N in a multistep process. Depending on the position of the CF3 group, different O,S-heterocycles or non-cyclic products were obtained. With 3-bromo-1,1,1-trifluorobut-3-en-2-ones derivatives of 1,4-oxathianes were formed, but isomeric 2-bromo-4,4,4-trifluorobut-2-en-1-ones yielded 1,3-oxathiolanes or non-cyclic sulfides. The thia-Michael addition is proposed as the initial step of the reaction, and the final heterocyclization is governed by the location of the CF3 group.
Rhodium(III)-catalyzed sp2 C-H bond addition to CF3-substituted unsaturated ketones
Jiang, Quanbin,Guo, Tenglong,Wu, Kaikai,Yu, Zhengkun
supporting information, p. 2913 - 2915 (2016/02/19)
Rhodium(iii)-catalyzed conjugate addition of aromatic and olefinic C-H bonds to CF3-substituted unsaturated ketones was efficiently achieved. Both arene and olefin substrates bearing a chelate assisted-directing group were coupled with a variet
Copper-catalyzed one-pot denitrogenative-dehydrogenative-decarboxylative coupling of β-ketoacids with trifluorodiazoethane: Facile access to trifluoromethylated aldol products
Xiong, Heng-Ying,Yang, Zhen-Yan,Chen, Zhen,Zeng, Jun-Liang,Nie, Jing,Ma, Jun-An
supporting information, p. 8325 - 8329 (2014/07/08)
A novel copper-catalyzed one-pot cross-coupling of β-ketoacids with in situ generated trifluorodiazoethane has been developed. This reaction provides a direct and efficient method, in which one C-C bond and one C-O bond were formed in a carbenoid center with concomitant denitrogenation-dehydrogenation- decarboxylation, to afford trifluoromethylated aldol products. In several preliminary experiments, good to high enantioselectivities were also obtained.
Isothiourea-mediated one-pot synthesis of functionalized pyridines
Stark, Daniel G.,Morrill, Louis C.,Yeh, Pei-Pei,Slawin, Alexandra M. Z.,O'Riordan, Timothy J. C.,Smith, Andrew D.
supporting information, p. 11642 - 11646 (2013/11/06)
Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/ lactamization, thiophenol elimination, and N- to O
