13679-74-8Relevant articles and documents
Synthesis of C3-symmetric nano-sized polyaromatic compounds by trimerization and Suzuki-Miyaura cross-coupling reactions
Kotha, Sambasivarao,Kashinath, Dhurke,Lahiri, Kakali,Sunoj, Raghavan B.
, p. 4003 - 4013 (2004)
Various C3-symmetric molecules were prepared by trimerization of acetyl aromatic compounds and subsequently coupled with various boronic acids under Pd0 catalysis conditions to generate oligoaryl/-heteroaryl C3-symmetric molecules. Several furan- and thiophene-containing star-shaped molecules were prepared by the use of Suzuki-Miyaura cross-coupling as a key step. Structural and conformational details were explored by semi-empirical molecular orbital theory using the AM1 method. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.
supporting information, p. 7683 - 7689 (2020/04/22)
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
Metal Sulfonate Polymers as Catalysts for the Heterogeneous Acylation of Aromatic Derivatives
Morizur, Vincent,Hector, Daphné,Olivero, Sandra,Desmurs, Jean Roger,Du?ach, Elisabet
supporting information, p. 3126 - 3129 (2016/07/12)
A series of metal sulfonate salts attached to a poly(ether ether ketone) (PEEK) polymer were prepared by ultrasonic activation and then examined as heterogeneous catalysts in the Friedel–Crafts acylation of aromatic derivatives.
Synthesis and characterization of AlCl3 impregnated molybdenum oxide as heterogeneous nano-catalyst for the Friedel-Crafts acylation reaction in ambient condition
Jadhav, Arvind H.,Chinnappan, Amutha,Hiremath, Vishwanath,Seo, Jeong Gil
, p. 8243 - 8250 (2015/11/27)
Aluminum trichloride (AlCl3) impregnated molybdenum oxide heterogeneous nano-catalyst was prepared by using simple impregnation method. The prepared heterogeneous catalyst was characterized by powder X-ray diffraction, FT-IR spectroscopy, solid-state NMR spectroscopy, SEM imaging, and EDX mapping. The catalytic activity of this protocol was evaluated as heterogeneous catalyst for the Friedel-Crafts acylation reaction at room temperature. The impregnated MoO4(AlCl2)2 catalyst showed tremendous catalytic activity in Friedel-Crafts acylation reaction under solvent-free and mild reaction condition. As a result, 84.0% yield of acyl product with 100% consumption of reactants in 18 h reaction time at room temperature was achieved. The effects of different solvents system with MoO4(AlCl2)2 catalyst in acylation reaction was also investigated. By using optimized reaction condition various acylated derivatives were prepared. In addition, the catalyst was separated by simple filtration process after the reaction and reused several times. Therefore, heterogeneous MoO4(AlCl2)2 catalyst was found environmentally benign catalyst, very convenient, high yielding, and clean method for the Friedel-Crafts acylation reaction under solvent-free and ambient reaction condition.
Cross-coupling reaction with lithium methyltriolborate
Yamamoto, Yasunori,Ikizakura, Kazuya,Ito, Hajime,Miyaura, Norio
, p. 430 - 439 (2013/03/13)
We newly developed lithium methyltriolborate as an air-stable white solid that is convenient to handle. The good performance of this triolborate for metal-catalyzed bond-forming reactions was demonstrated in palladium-catalyzed cross-coupling reactions wi
Synthesis of 3-(5-methylthiophen-2-yl)coumarins and their photochromic dihetarylethene derivatives
Bochkov, Andrei Y.,Krayushkin, Mikhail M.,Yarovenko, Vladimir N.,Barachevsky, Valery A.,Beletskaya, Irina P.,Traven, Valery F.
, p. 891 - 898 (2013/08/23)
Novel unsymmetrical di(thienyl)maleic acid anhydride, including coumarin moiety, has been designed and synthesized. Its photochromism study and fatigue resistance estimation are reported. Microwave-assisted procedure has been successfully used for synthesis of 3-(5-methylthiophen-2-yl)coumarins.
Novel dithienylethenes with extended π-systems: Synthesis by aldol condensation and photochromic properties
Altenhoener, Kai,Lamm, Jan-Hendrik,Mattay, Jochen
experimental part, p. 6033 - 6037 (2011/02/23)
A facile and stereoselective route to symmetric π-extended dithienylethene derivatives is described. The key step of this route is an aldol condensation of 1,2-bis(5-formyl-2-methylthiophen-3-yl)cyclopentene with a large variety of acyl compounds. All synthesized photoswitches can be reversibly converted into the closed form by irradiation with visible light. The photochromic properties of nine new dithienylethenes are discussed. A new synthetic pathway leading to π-extended dithienylethenes is presented. Nine new photoswitches are obtained in a facile and very stereoselective procedure and their photochromic properties are discussed.
PROCESS FOR PRODUCING 2-ACYLTHIOPHENE COMPOUND
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Page/Page column 7, (2008/06/13)
The present invention provides a process for producing a 2-acylthiophene compound which has a low content of the 3-isomer generated as a by-product, the process comprising reacting a thiophene compound represented by formula (1) : wherein R1 is a hydrogen atom, a C1-6 alkyl group, a phenyl group, or a halogen atom, with at least one member selected from the group consisting of acid anhydrides represented by formula (2): wherein R2 is a C1-6 alkyl group or a phenyl group, and acid halides represented by formula (3): wherein R2 is as defined above and X is a halogen atom, in the presence of a solid acid catalyst at a temperature less than 75°C in the absence of solvent, thus producing a 2-acylthiophene compound represented by formula (4): wherein R1 and R2 are as defined above.
Kinetics of the Detritiation of a Series of 4- and 5-Substituted 2-(acetyl)thiophenes
Jones, John R.,Pearson, Gerd M.,Spinelli, Domenico,Consiglio, Giovanni,Arnone, Caterina
, p. 557 - 558 (2007/10/02)
A series of 4- and 5-substituted 2-(acetyl)thiophenes have been prepared and the kinetics of the hydroxide-catalysed detritiation studied at 25.0 deg C.The second-order detritiation rate constants parallel those observed for the corresponding meta- and para-substituted acetophenones but as the reaction constant ρ is higher (1.61) the range of reactivity is much wider than that witnessed for the acetophenones.
Deoxygenation of Allylic Carbinolamides and Related Alcohols by Acidic Sodium Cyanoborohydride: Scope and Limitations
Drage, James S.,Earl, Richard A.,Vollhardt, K. Peter C.
, p. 701 - 702 (2007/10/02)
Acidic sodium cyanoborohydride reduces allylic and other substituted carbinolamides to the corresponding deoxygenated compounds, whereas other similar alcohols are unreactive or undergo alternative transformations.
