4433-13-0Relevant articles and documents
Supported gold catalyzes the homocoupling of phenylboronic acid with high conversion and selectivity
Carrettin, Silvio,Guzman, Javier,Corma, Avelino
, p. 2242 - 2245 (2005)
(Chemical Equation Presented) Gold on nanocrystalline cerium oxide is a highly active and selective catalyst for the homocoupling of phenylboronic acid derivatives in the presence of K2CO3 as a base (see picture). Au3+ species are thought to be the active sites for the reaction, and water is required to activate the boronic acid through the participation of surface hydroxy groups.
Synthesis of Rolivsans containing unsaturated biphenyl units by acid-catalyzed transformations of 4,4′-di(1-hydroxyethyl)biphenyl
Zaitsev,Khramova,Shvabskaya
, p. 783 - 789 (2007)
The mechanism and kinetics of formation, and also the structure, composition, and properties of thermosetting resins of a new class, Rolivsans with biphenyl units, were studied.
"benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers
Minus, Matthew B.,Moor, Sarah R.,Pary, Fathima F.,Nirmani,Chwatko, Malgorzata,Okeke, Brandon,Singleton, Josh E.,Nelson, Toby L.,Lynd, Nathaniel A.,Anslyn, Eric V.
supporting information, p. 2873 - 2877 (2021/05/05)
Typically, Suzuki couplings used in polymerizations are performed at raised temperatures in inert atmospheres. As a result, the synthesis of aromatic materials that utilize this chemistry often demands expensive and specialized equipment on an industrial scale. Herein, we describe a bimetallic methodology that exploits the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations that can be performed on a benchtop under ambient conditions. These couplings are facile and can be performed by simple mixing in the open vessel. To demonstrate the utility of this method in the context of polymer synthesis: polyfluorene, polycarbazole, polysilafluorene, and poly(6,12-dihydro-dithienoindacenodithiophene) were created at ambient temperature and open to air.
A porous Br?nsted superacid as an efficient and durable solid catalyst
Sun, Qi,Hu, Kewei,Leng, Kunyue,Yi, Xianfeng,Aguila, Briana,Sun, Yinyong,Zheng, Anmin,Meng, Xiangju,Ma, Shengqian,Xiao, Feng-Shou
supporting information, p. 18712 - 18719 (2018/10/15)
The development of catalysts able to assist industrial chemical transformations is a topic of high importance. In view of the versatile catalytic capabilities of acid catalysts, extensive research efforts are being made to develop porous superacid materials with a high density of accessible active sites to replace molecular acid catalysts. Herein, we report the rational development of a porous Br?nsted superacid by combining important elements that target high strength acidity into one material, as demonstrated by grafting the sulfonic acid group onto a highly fluorinated porous framework, where the acid strength and stability are greatly enhanced by an electron-withdrawing environment provided by the polymer backbone, reminiscent of that seen in Nafion resin. In addition, the densely arranged acid groups that are confined in the three-dimensional nanospace facilitate the transfer of hydrons, thereby further increasing the acidity. By virtue of the pore structure and strong acidity, this system exhibits excellent performance for a wide range of reactions, far outperforming commercial acid resins under repeated batch and flow reaction conditions. Our findings demonstrate how this synthetic approach may instruct the future design of heterogeneous acid catalysts with advantageous reaction capabilities and stability.
Efficient Homocoupling of Aryl- and Alkenylboronic Acids in the Presence of Low Loadings of [{Pd(μ-OH)Cl(IPr)} 2 ]
Ostrowska, Sylwia,Rogalski, Szymon,Lorkowski, Jan,Walkowiak, Jedrzej,Pietraszuk, Cezary
supporting information, p. 1735 - 1740 (2018/07/21)
NHC-palladium(II) complex [{Pd(μ-OH)Cl(IPr)} 2 ] (IPr = bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) catalyzes the oxidative coupling of a broad spectrum of aryl- and alkenylboronic acids at loadings down to 5 ppm. At the concentration of 0.05 mol% the catalyst permits an efficient reaction under base-free conditions.
A new class of stereoregular vinylene-arylene copolymers with double-decker silsesquioxane in the main chain
Zak, Patrycja,Dudziec, Beata,Dutkiewicz, Micha?,Ludwiczak, Monika,Marciniec, Bogdan,Nowicki, Marek
, p. 1044 - 1055 (2016/03/12)
A synthesis of a new macromolecular class of vinylene-arylene copolymers with double-decker silsesquioxane in the main chain is presented. Two transition-metal-catalyzed processes, which is silylative-coupling copolycondensation (SCC) and ADMET copolymerization of divinyl-substituted double-decker silsesquioxanes (DDSQ-2SiVi) with selected diolefins, are reported to be highly efficient tools for the formation of stereoregular copolymers containing DDSQ-silylene-vinylene-arylene units. The copolymeric products are studied in terms of their structural, thermal, and mechanical properties.
Ligand-, base-, co-catalyst-free copper fluorapatite (CuFAP) as a versatile, ecofriendly, heterogeneous and reusable catalyst for an efficient homocoupling of arylboronic acid at ambient reaction conditions
Mulla, Shafeek A. R.,Chavan, Santosh S.,Pathan, Mohsinkhan Y.,Inamdar, Suleman M.,Shaikh, Taufeekaslam M. Y.
, p. 24675 - 24680 (2015/03/30)
This paper describes the first report in which copper species containing copper fluorapatite (CuFAP) acts as a versatile, eco-friendly, recyclable, heterogeneous catalyst for an efficient synthesis of symmetric biaryls from the homo-coupling of arylboronic acids in methanol solvent at ambient reaction conditions. The developed protocol is ligand-, base-, and co-catalyst-free, sustainable, mild, inexpensive, and compatible with a wide range of aromatic/heterocyclic boronic acids and provides the corresponding products in excellent yields without purification. The catalyst was easily recovered from the reaction mixture and reused several times without loss of activity.
Synthesis of 4-vinylbiphenyl derivatives by Pd(II)-1,2-diaminocyclohexane complex catalyzed Suzuki-Miyaura reaction
Liu,Ma,Liu,Xie,Dai
, p. 8022 - 8024 (2015/02/02)
A series of 4-vinylbiphenyl derivatives were synthesized by Pd(II)-1,2-diaminocyclohexane complex catalyzed Suzuki-Miyaura reactions in the presence of K3PO4?3H2O as base in toluene at 80 ° C and the corresponding products achieved 39-95% yields. According to this efficient C-C bond-forming method, the obtained yields of 4-vinylbiphenyl liquid crystal compounds were up to 89%.
A highly stereoselective synthesis of new styryl-π-conjugate organosilicon compounds
Majchrzak, Mariusz,Hybsz, Milena,Kostera, Sylwia,Kubicki, Maciej,Marciniec, Bogdan
supporting information, p. 3055 - 3058 (2014/05/20)
This work describes very precise and controlled catalytic transformations as useful tools for the synthesis of new trans-π-conjugated molecular and macromolecular organosilicon compounds. Several distyryl-arenes were obtained efficiently via silylative coupling in high yields and with excellent selectivity for new E,E-bis(silyl)arenes.
Synthesis of new styrylarenes via Suzuki-Miyaura coupling catalysed by highly active, well-defined palladium catalysts
Kostera, Sylwia,Kownacki, Ireneusz,Kubicki, Maciej,Majchrzak, Mariusz
supporting information, p. 15535 - 15539 (2015/11/25)
An efficient synthetic route for well-defined palladium(0) complexes [Pd(η2-dba)(PPh3)2] (2), [Pd(η2-dba)(PCy3)2] (3) and their crystallographic structures is reported. This is the first crystallographic characterization of palladium complexes coordinated with one dibenzylideneacetone and two phosphines. A highly effective, fully controlled method for selective synthesis of mono- (5-9) and distyrylarenes (10-15) via Suzuki-Miyaura coupling is described. ? The Royal Society of Chemistry 2013.
