- Synthesis and basic properties of tetrathieno[2,3-a:3′,2′-c: 2″,3″-f:3a€?,2a€?-h]naphthalene: A new π-conjugated system obtained by photoinduced electrocyclization- dehydrogenation reactions of tetra(3-thienyl)ethene
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A method for the synthesis of tetrathieno[2,3-a:3′,2′-c: 2″,3″-f:3a€?,2a€?-h]naphthalene (3), utilizing photoinduced electrocyclization-dehydrogenation reactions of tetra(3-thienyl)ethene (1), was developed. Photoirradiation of a toluene or CHCl3 solution of 1, containing a small amount of I2, leads to modestly efficient production of 3. In contrast to the UV-vis absorption property of the typical p-type organic transistor material pentacene, that of 3 does not experience a time-dependent change under aerated conditions, indicating that 3 has high stability against molecular oxygen. The results of X-ray crystallographic analysis demonstrate that 3 possesses a columnar crystalline structure in which molecules are aligned in a face-to-face manner with a high degree of the π-π overlap between adjacent molecules. This phenomenon should result in efficient charge-carrier transport properties of the crystalline form of this substance.
- Yamamoto, Atsushi,Ohta, Eisuke,Kishigami, Nao,Tsukahara, Norihiro,Tomiyori, Yusuke,Sato, Hiroyasu,Matsui, Yasunori,Kano, Yusuke,Mizuno, Kazuhiko,Ikeda, Hiroshi
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- Method for preparing symmetric diarylketone through catalytic oxidative carbonylation
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The invention discloses a method for preparing symmetric diarylketone of a formula (I) as shown in the description. The method comprises the following steps: mixing arylboronic acid (II) (Ar-B(OH)2 (II)), a palladium catalyst, a promoter and an organic solvent in a reactor, introducing air and CO having a volume ratio of (7-19):1, reacting under the conditions of a pressure of 1-6 atm and a temperature of 30-80 DEG C for 8-16 hours, and performing after-treatment on the reaction solution, thereby obtaining the product symmetric diarylketone. According to the method disclosed by the invention,the air directly serves as an oxidizing agent to replace the O2 to be applied to oxidative carbonylation of the arylboronic acid, and the ratio of the air to CO is beyond an explosion limit. Therefore, the catalytic system is safe and economic. The palladium catalyst is small in dosage and simple in separation and can be recycled for several times. The method disclosed by the invention is mild inreaction condition, excellent in substrate suitability and high in yield.
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Paragraph 0023; 0024; 0025; 0026; 0030
(2019/03/08)
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- Ligand-free Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Iodides in Aqueous CH3CN with Sub-stoichiometric Amount of Mo(CO)6 as CO Source
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A new method for the synthesis of diaryl and heterodiaryl ketones has been established based on the palladium-catalyzed carbonylative Suzuki coupling approach with sub-stoichiometric Mo(CO)6 as CO source. Using 0.5 mol% of Pd(TFA)2 as catalyst, 0.5 equivalent of Mo(CO)6 as solid carbonyl reagent and 3 equivalent of K3PO4 as base, a wide range of functionalized (hetero)aryl iodides and (hetero)aryl boronic acids could smoothly proceed the carbonylative cross-coupling reaction in aqueous CH3CN at 50 °C, affording the corresponding ketones in good to excellent yields. The newly developed method was easy to operate under mild conditions with high efficiency. (Figure presented.).
- Sun, Nan,Sun, Qingxia,Zhao, Wei,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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p. 2117 - 2123
(2019/03/28)
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- Nickel-Catalyzed Molybdenum-Promoted Carbonylative Synthesis of Benzophenones
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A nickel-catalyzed molybdenum-promoted carbonylative coupling reaction for the synthesis of benzophenones from aryl iodides has been developed. Various substituted diaryl ketones were synthesized in moderate to excellent yields under CO-gas-free conditions. A synergetic effect of both nickel and molybdenum has been observed, which is also responsible for the success of this transformation.
- Peng, Jin-Bao,Wu, Fu-Peng,Li, Da,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
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p. 6788 - 6792
(2018/06/04)
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- Synthetic method of ketone compounds
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The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of ketone compounds. The invention provides a synthetic method of the ketone compounds. In the presence of a silver catalyst and alkaline additive, hydrazine and carbonyl carboxylic acid are used as substrates to have oxidation reaction to generate the ketone compounds. In the synthetic method of the invention, the used substrates, catalyst and additive are easy to obtain, and the cost is low; meanwhile, the generated byproducts are nitrogen, water and carbon dioxide, so that the synthetic method is environmentally friendly, pollution-free, and capable of meeting the sustainable development concept; and thirdly, by adopting the preparation method, the pre-activation is not needed, the yield is greater than 60 percent or, and the synthetic efficiency is high; and the technical defects in the prior art that the synthesis method of the ketone compounds is complicated in synthetic procedures, high in catalyst price and difficult in synthesizing an active intermediate can be solved.
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Paragraph 0077-0081
(2018/11/22)
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- Palladium-Catalyzed Carbonylative Homocoupling of Aryl Iodides for the Synthesis of Symmetrical Diaryl Ketones with Formic Acid
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A convenient method for the palladium-catalyzed carbonylative homocoupling of aryl iodides was developed. With formic acid as the CO source, various symmetrical diaryl ketones were synthesized in moderate to good yield in the presence of a palladium catalyst.
- Wu, Fu-Peng,Peng, Jin-Bao,Qi, Xinxin,Wu, Xiao-Feng
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p. 173 - 177
(2017/11/27)
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- Synthesis of Symmetrical Diaryl Ketones by Cobalt-Catalyzed Reaction of Arylzinc Reagents with Ethyl Chloroformate
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Symmetrical diaryl ketones were prepared by a cross-coupling reaction between aryl bromides and ethyl chloroformate. This new method, which uses a catalyst composed of CoBr2and a bipyridine ligand along with readily available starting materials, allows for the synthesis of a variety of symmetrical diaryl ketones in moderate to excellent yields (37–99 %) under mild conditions. This reaction, in which ethyl chloroformate acts as a surrogate of carbon monoxide in the presence of cobalt and zinc, represents an interesting alternative to previously known approaches for the synthesis of diarylmethanones.
- Rérat, Alice,Michon, Christophe,Agbossou-Niedercorn, Francine,Gosmini, Corinne
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p. 4554 - 4560
(2016/09/23)
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- Palladium-catalyzed oxidative carbonylation for the synthesis of symmetrical diaryl ketones at atmospheric co pressure
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A mild and efficient synthesis of symmetrical diaryl ketones by palladium-catalyzed oxidative carbonylation of arylboronic acids with carbon monoxide at atmospheric pressure is reported. Georg Thieme Verlag Stuttgart New York.
- Li, Yang,Lu, Wei,Xue, Dong,Wang, Chao,Liu, Zhao-Tie,Xiao, Jianliang
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supporting information
p. 1097 - 1100
(2014/05/20)
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- A general synthesis of diarylketones by means of a three-component cross-coupling of aryl and heteroaryl bromides, carbon monoxide, and boronic acids
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Pd(OAc)2/di-1-adamantyl-n-butylphosphine (cataCXium A) is highly active in the three-component Suzuki carbonylation and represents the most general catalyst system reported up to now. A broad range of aryl/heteroaryl bromides and aryl boronic acids can be coupled to the corresponding diarylketones at low catalyst loadings.
- Neumann, Helfried,Brennfuehrer, Anne,Beller, Matthias
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experimental part
p. 3645 - 3652
(2009/04/11)
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- A short synthesis of 3,3-di(hetero)arylpropylamines obtained from bis-(hetero)aryl ketones via palladium catalysis
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A palladium-catalyzed parallel synthesis of bis-hetero(aryl) ketones is described with two further synthetic steps allowing easy entry to 3,3-di(hetero)arylpropylamines.
- Martyres, Domnic,Schmiedt, Frank
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p. 1649 - 1651
(2007/10/03)
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- 3-(diheteroarylmethylene)-8-azabicyclo[3.2.1]octane and 3-((aryl)(heteroaryl)methylene)-8-azabicyclo[3.2.1]octane derivatives
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This invention is directed to 3-(diheteroarylmethylene)-8-azabicyclo[3.2.1] octane and 3-((aryl)(heteroaryl)methylene)-8-azabicyclo[3.2.1] octane derivatives useful as δ-opioid, μ-opioid, or δ-opioid and μ-opioid receptor receptor modulators. Depending on
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Page/Page column 23
(2010/02/13)
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- Ultrafast Chemistry: Cobalt Carbonyl-Mediated Synthesis of Diaryl Ketones under Microwave Irradiation
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(Equation Presented) By combining the advantages of metal activation, in situ carbon monoxide delivery, and microwave heating, benzophenones were efficiently synthesized in 6-10 s. These ultrafast carbonylation reactions occur under air by flash heating o
- Enquist, Per-Anders,Nilsson, Peter,Larhed, Mats
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p. 4875 - 4878
(2007/10/03)
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- Expedient synthesis of symmetric aryl ketones and of ambient-temperature molten salts of imidazole
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A short procedure for the synthesis of 2,2-di(3-thienyl)-1,3-dioxolan is described. The route developed is convenient (only two synthetic and one chromatographic steps are required) and efficient (66% overall yield from 3-bromothiophene). This compound was transformed into the ketone, cyclopenta[2,1-b:3',4'-b']dithiophen-4-one by a known process. Optimized syntheses of symmetric aryl ketones, 1-alkyl-3-methylimidazolium and 1-alkyl-2-methyl-3-methylimidazolium liquid salts are also reported.
- Lucas,El Mehdi,Ho,Belanger,Breau
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p. 1253 - 1258
(2007/10/03)
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