34352-74-4Relevant academic research and scientific papers
Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe3
Wang, Xiu,Wang, Zhenhua,Asanuma, Yuya,Nishihara, Yasushi
supporting information, p. 3640 - 3643 (2019/05/17)
Bidentate phosphine-assisted methylenation of acyl fluorides and acyl chlorides with substituted with aryl, alkenyl, and alkyl groups trimethylaluminum afforded an array of 2-substituted propene derivatives. The addition of a catalytic amount of DPPM increased an efficiency of the reactions. Trimethylaluminum as the methylenation reagent not only eliminates the presynthesis of methylene transfer reagent, but provides an efficient method for the synthesis of a series of 2-substituted propenes.
Method for selectively oxidizing cumene compounds
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Paragraph 0105; 0106, (2019/11/21)
The invention relates to a method for selectively oxidizing cumene compounds, and the method comprises the following steps: placing cumene compounds shown in a formula (I), an iron porphyrin catalyst,an oxidant and a dispersant into a ball milling tank, sealing the ball milling tank, performing ball milling for 3 to 24 hours at a rotating speed of 100 to 800 rpm at room temperature, stopping ballmilling once every 1 to 3 hours in the ball milling process, discharging gases in the ball milling tank, finishing the reaction, and performing post-treatment on a reaction mixture to obtain product2-phenyl-2-propanol compound shown in a formula (II); according to the invention, the oxidation conversion of the cumene and derivatives thereof is realized through solid-phase ball milling, the reaction mode is novel, the operation is convenient, and the energy consumption is low; the method needs no organic solvent, thus effectively avoiding the use of toxic and harmful organic solvents and being green and environment-friendly; has low peroxide content and high safety factor, and high 2-phenyl-2-propanol and derivative selectivity and meets the social requirements of the current green chemical process, environmental compatibility chemical process and biological compatibility chemical process.
Catalytic Lactonization of Unactivated Aryl C-H Bonds with CO2: Experimental and Computational Investigation
Song, Lei,Zhu, Lei,Zhang, Zhen,Ye, Jian-Heng,Yan, Si-Shun,Han, Jie-Lian,Yin, Zhu-Bao,Lan, Yu,Yu, Da-Gang
supporting information, p. 3776 - 3779 (2018/07/21)
The first catalytic lactonization of unactivated aryl C-H bonds with CO2 to afford important phthalides is reported. Notably, this method features high selectivity, excellent functional group tolerance, smooth scalability, and facile product diversification. DFT calculations reveal that a novel insertion of two CO2 into the O-Pd bond of a palladacycle might be the key step, providing great potential and a different perspective for carbonylation with CO2.
The cumene/O2 system: A very simple tool for the radical chain oxidation of some functional groups
Malekafzali,Malinovska,Patureau
supporting information, p. 6981 - 6985 (2017/08/02)
Due to the relative stability of the cumyl radical, cumenes and α-methyl-styrenes are ideally structured to directly harvest the oxidizing reactivity of O2 and initiate radical chain reactions in catalyst-free conditions. In the absence of additional substrates, these processes can lead to acetophenones. In the presence of substrates, the cumene oxidation process can be intercepted in various chain reactions, affording very simple protocols for functional group oxidation.
Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes
Shirini, Farhad,Khaligh, Nader Ghaffari,Akbari-Dadamahaleh, Somayeh
, p. 15 - 23 (2013/01/14)
Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.
The process of 4-hydroxybiphenyl synthesis from 4-isopropylbiphenyl
Stec, Zbigniew,Orlinska, Beata,Jakubowski, BartLomiej,Zawadiak, Jan
, p. 527 - 532 (2008/12/22)
The kinetics of the oxidation of 4-isopropylbiphenyl (1) in the liquid phase by oxygen to 1 -(1,1′-biphenyl-4-yl)-1 -methylethyl hydroperoxide (2) was investigated. The oxidizability of 1 in the temperature range from 60°C to 120°C and the overall energy activation of oxidation were determined. Long-term oxidation of 1 to 2 in the temperature range of 80-120°C was investigated, and the yield and selectivity of the process were determined. Pure 2 was obtained, and its properties were defined. 4-Hydroxybiphenyl was obtained as a result of the acidic decomposition of 2.
Palladium- and nickel-catalyzed cross-couplings of unsaturated halides bearing relatively acidic protons with organozinc reagents
Manolikakes, Georg,Munoz Hernandez, Carmen,Schade, Matthias A.,Metzger, Albrecht,Knochel, Paul
supporting information; experimental part, p. 8422 - 8436 (2009/04/11)
(Chemical Equation Presented) A wide range of polyfunctional aryl, heteroaryl, alkyl, and benzylic zinc reagents were coupled with unsaturated aryl halides bearing an acidic NH or OH proton, using Pd(OAc)2 (1 mol %) and S-Phos (2 mol %) as catalyst without the need of protecting groups. A similar nickel-catalyzed reaction is described. The relative kinetic basicity of organozinc compounds as well as their stability toward acidic protons is also described.
Efficient Synthesis and Resolution of trans-2-(1-Aryl-1-methylethyl)cyclohexanols; Practical Alternatives to 8-Phenylmenthol
Comins, Daniel L.,Salvador James M.
, p. 4656 - 4661 (2007/10/02)
A short synthesis and resolution of effective chiral auxiliaries of the 8-arylmenthol-type achieved using inexpensive materials, a recyclable lipase, and easily applied procedures that are amenable to large-scale preparation.A variety of isopropylarenes were α-metalated with n-butylithium/potassium tert-pentoxide and treated with cyclohexene oxide to provide racemic trans-2-(1-aryl-1-methylethyl)cyclohexanols 6a-f in fair to high yield.Candida rugosa lipase and lauric acid were used to resolve these racemic alcohols by converting the (-)-enantiomer to its laurateester.The enzymatic resolutions were carried out at 40 deg C and were faster in cyclohexane than in hexanes.The synthesis and resolution of racemic trans-2-(1-methyl-1-phenylethyl)cyclohexanol (6a) were performed on a 1 mol scale in 68 percent overall yield, requiring three steps for (+)-6a and five steps for (-)-6a.
