- HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: Synthesis of CF3-indenes and DFT study of intermediate carbocations
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The reaction of CF3-propargyl alcohols [ArCCCH(OH)CF3] with arenes under the action of acidic HUSY zeolite CBV-720 was investigated. It was found that the reaction at 100 °C for 1 h gave rise to 3-aryl-1-CF3-indenes in up
- Nursahedova, Selbi K.,Zerov, Aleksey V.,Boyarskaya, Irina A.,Grinenko, Elena V.,Nenajdenko, Valentine G.,Vasilyev, Aleksander V.
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- Catalytic Synthesis of Trifluoromethylated Allenes, Indenes, Chromenes, and Olefins from Propargylic Alcohols in HFIP
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A general method to access CF3-substituted allenes from propargylic alcohols under Lewis acid catalysis in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvent is described. By tuning the reaction time and temperature, the obtained allenes rearr
- No?l, Florent,Vukovi?, Vuk D.,Yi, Jing,Richmond, Edward,Kravljanac, Pavle,Moran, Joseph
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p. 15926 - 15947
(2019/12/25)
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- Ni-Catalyzed Defluorination for the Synthesis of gem-Difluoro-1,3-dienes and Their [4 + 2] Cycloaddition Reaction
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A nickel-catalyzed defluorination of α-trifluoromethylated allyl/propargyl carbonates using bis(pinacolato)diboron (B2pin2) as a reactant is described. The reaction proceeds under relatively mild reaction conditions, providing conjug
- Zhou, Minqi,Zhang, Jian,Zhang, Xing-Guo,Zhang, Xingang
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supporting information
p. 671 - 674
(2019/01/21)
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- Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones
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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
- Ramasamy, Manickavasakam,Lin, Hui-Chang,Kuo, Sheng-Chu,Hsieh, Min-Tsang
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supporting information
p. 356 - 360
(2019/02/12)
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- Gold-catalyzed synthesis of β-trifluoromethylated α,β-unsaturated ketones from CF3-substituted propargylic carboxylates and their reactivity in Diels-Alder reactions
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The synthesis of fluorinated synthetic intermediates has become a field of intense research in organic chemistry. In this article, we report the application of a gold-catalyzed rearrangement to the synthesis of β-trifluoromethylated α,β-unsaturated ketone
- Boreux, Arnaud,Lambion, Aubin,Campeau, Dominic,Sanita, Marina,Coronel, Ruben,Riant, Olivier,Gagosz, Fabien
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supporting information
p. 5232 - 5239
(2018/06/01)
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- Method for synthesizing second-level trifluoromethyl propargyl alcohol
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The invention discloses a method for synthesizing second-level trifluoromethyl propargyl alcohol. The method comprises the following steps: enabling 2-iodo benzoic acid and sodium periodate to react so as to generate 1-(hydroxyl)-1,2-iodobenzoyl-3(1H)-ket
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Paragraph 0067; 0068; 0069
(2017/07/20)
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- Synthesis of Trifluoromethyl-allenes by Gold-Catalyzed Rearrangement of Propargyl Benzyl Ethers
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A new method for the synthesis of trifluoromethyl-allenes from easily accessible α-trifluoromethyl-propargyl benzyl ether derivatives following a gold-catalyzed intramolecular hydride transfer has been developed. Various di- and trisubstituted trifluoromethyl-allenes were obtained in good to excellent yields.
- Boreux, Arnaud,Lonca, Geoffroy H.,Riant, Olivier,Gagosz, Fabien
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supporting information
p. 5162 - 5165
(2016/10/14)
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- Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification
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In order to obtain optically active fluorinated propargyl alcohols, a lipase-catalyzed kinetic resolution has been carried out. The effect of lipase types, organic solvents, reaction temperature, and acyl donors was examined in the lipase-catalyzed transe
- Ko, Sung-Jin,Lim, Jung Yun,Jeon, Nan Young,Won, Keehoon,Ha, Deok-Chan,Kim, Bum Tae,Lee, Hyuk
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experimental part
p. 1109 - 1114
(2009/09/30)
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- Fluoride-catalyzed nucleophilic perfluoroalkylations of acetylenic ketones or aldehydes
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Reactions of 4-phenylbut-3-yn-2-one (1a) and phenylpropynal (1b) with trimethyl(perfluoroalkyl)silanes (Me3SiRf) (Rf = CF3, C2F5, n-C6F13, n-C7F15/sub
- Manandhar, Sudha,Singh, Rajendra P.,Shreeve, Jean'ne M.
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p. 1296 - 1304
(2007/10/03)
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- Reduction of metal-stabilized α-CF3-carbenium ion complexes under mild conditions: Synthesis, structures, and reactivity
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Complexed α-CF3 propargyl alcohols of the general formula [(M2L6)(μ-η2,η2-RC?CCH(CF3)(OH))] were prepared with M2L6 = CO2(CO)6, R = CH3/sub
- Gruselle, Michel,Malezieux, Bernard,Andres, Roman,Amouri, Hani,Vaissermann, Jacqueline,Melikyan, Gagik G.
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p. 359 - 368
(2007/10/03)
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- SYNTHETIC APPROACH TO STEREOISOMERS OF ALLYLIC ALCOHOLS POSSESING A TRIFLUOROMETHYL GROUP
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A number of stereoisomers of optically pure allylic alcohols with a trifluoromethyl group were prepared, utilizing the enantiotopic specifity of assymetric hydrolysis of their acetates by hydrolyses.Their absolute configurat
- Kitazume, Tomoya,Lin, Jeng Tain,Yamazaki, Takashi,Takeda, Mitsunori
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p. 177 - 188
(2007/10/02)
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- Addition of Organocuprates to Acetylenic Di- and Trifluoromethyl Ketones. Regiospecific Synthesis of β,β-Disubstituted Unsaturated Fluoro ketones
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A regiospecific synthesis of β,β-disubstituted-α,β-unsaturated di- and trifluoromethyl ketones has been achieved by the conjugate addition of higher order cyano cuprate reagents to acetylenic di- and trifluoromethyl ketones.An efficient and reproducible s
- Lindermann, Russel J.,Lonikar, Madhu S.
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p. 6013 - 6022
(2007/10/02)
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- AN EFFICIENT PROCEDURE FOR THE OXIDATION OF FLUORINATED CARBINOLS
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The oxidation of di and trifluorocarbinols has been accomplished in high yields using the Dess-Martin periodane oxidant.
- Linderman, Russell J.,Graves, David M.
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p. 4259 - 4262
(2007/10/02)
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- PREPARATION OF TRIFLUOROMETHYLATED ALLYLIC ALCOHOLS FROM TRIFLUOROACETALDEHYDE AND ORGANOMETALLIC COMPOUNDS
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A number of allylic alcohols bearing a trifluoromethyl group at the α- or γ-position, and α-trifluoromethylated γ-enols and -ynols were prepared by the reaction of trifluoroacetaldehyde with a variety of organometallic compounds.Most of the Reformatsky- or Grignard-type reactions required promotion by ultrasonic irradiation.
- Ishikawa, Nobuo,Koh, Moon Gyu,Kitazume, Tomoya,Choi, Sam Kwon
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p. 419 - 430
(2007/10/02)
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