34288-40-9Relevant academic research and scientific papers
PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
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, (2021/12/08)
The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
The Employment of Sodium Hydride as a Michael Donor in Palladium-catalyzed Reductions of α, β-Unsaturated Carbonyl Compounds
Liu, Ye,Mao, Yujian,Hu, Yanwei,Gui, Jingjing,Wang, Liang,Wang, Wei,Zhang, Shilei
supporting information, p. 1554 - 1558 (2019/02/16)
Sodium hydride was employed as a Michael donor under the catalysis of PdCl2 for 1,4-conjugate reductions of α, β-unsaturated carbonyl compounds, which features operational simplicity, mild conditions and high atom-economy. The merits of NaH as a reductant were demonstrated by the one-pot or cascade reactions for the syntheses of complex molecules. (Figure presented.).
Functionalized β-cyclodextrin as supramolecular ligand and their Pd(OAc)2 complex: Highly efficient and reusable catalyst for Mizoroki-Heck cross-coupling reactions in aqueous medium
Dindulkar, Someshwar D.,Jeong, Daham,Kim, Hwanhee,Jung, Seunho
, p. 85 - 94 (2016/06/01)
A novel class of water soluble palladium complexes with recognition abilities based on functionalized β-cyclodextrin has been synthesized. The complex demonstrated high catalytic activity and a supramolecular platform for phosphine-free Mizoroki-Heck cross-coupling reactions in water. The efficient arylation of alkenes was carried out using different iodo- and bromo-arenes with good to excellent yields (up to 96%). The advantages, like recyclability of catalysts, operational simplicity and accessibility in aqueous medium, make this protocol eco-friendly.
Scope and Limitation of the Microwave-Assisted Catalytic Wittig Reaction
Hoffmann, Marcel,Deshmukh, Sunetra,Werner, Thomas
, p. 4532 - 4543 (2015/07/27)
We have developed a microwave-assisted catalytic Wittig reaction. In this paper, we give full account of the scope and limitations of this reaction. A screening of various commercially available phosphine oxides as precatalysts revealed Bu3P=O to be the most promising candidate. We tested 10 silanes for the in situ reduction of the phosphine oxide to generate Bu3P as the actual catalyst. Different epoxides were tested as masked bases. In this context, cyclohexene oxide as well as butylene oxide proved to be suitable. The reaction could be carried out at 125 C, but higher yields and E/Z selectivities were obtained at 150 °C. Under the optimised reaction conditions, more than 40 examples for the conversion of various aldehydes into the corresponding alkenes are reported. The products were obtained in yields of up to 88 with high E selectivities. Moreover, we also describe the further screening of several chiral phosphines as catalysts for the microwave-assisted enantioselective catalytic Wittig reaction. The scope and limitations of the microwave-assisted catalytic Wittig reaction have been evaluated with respect to the catalyst, silane, solvent, reaction conditions, and substrates.
Multicomponent, flow diazotization/mizoroki-heck coupling protocol: Dispelling myths about working with diazonium salts
Nalivela, Kumara S.,Tilley, Michael,McGuire, Michael A.,Organ, Michael G.
supporting information, p. 6603 - 6607 (2014/06/09)
A single pass flow diazotization/Mizoroki-Heck protocol has been developed for the production of cinnimoyl and styryl products. The factors that govern aryl diazonium salt stability have been examined in detail leading to the development of a MeOH/DMF co-solvent system in which the diazonium salts can be generated in the presence of all other reaction components and then coupled selectively to give the desired products. Finally the key role of the reaction quench for flow reactions has been demonstrated.
First Microwave-Assisted Catalytic Wittig Reaction
Werner, Thomas,Hoffmann, Marcel,Deshmukh, Sunetra
supporting information, p. 6873 - 6876 (2016/02/19)
We introduce a novel catalytic Wittig reaction based on an inexpensive and readily available phosphane oxide as a precatalyst. The performance of the reaction under microwave irradiation led to significantly improved yields and reaction rates relative to those obtained under conventional heating. Moreover, herein we enclose the first example of the asymmetric catalytic Wittig reaction based on a chiral phosphane as the catalyst.
Sustainable heck-matsuda reaction with catalytic amounts of diazonium salts: An experimental and theoretical study
Susperregui, Nicolas,Miqueu, Karinne,Sotiropoulos, Jean-Marc,Lecallonnec, Francois,Fouquet, Eric,Felpin, Francois-Xavier
experimental part, p. 7210 - 7218 (2012/07/27)
The palladium-catalyzed Heck-Matsuda reaction with a catalytic amount of an in-situ-generated diazonium salt proceeded under mild and sustainable conditions. The reaction proceeded at room temperature, under base-free conditions, and only generated tBuOH, H2O, and N2 as by-products. Ortho-substituted diazonium salts were more-efficiently coupled to methyl acrylate than their corresponding paraisomers, which required the addition of anisole as an additive. In support of these experimental data, we carried out theoretical studies to gain a deeper understanding of these reaction outcomes.
Tandem reduction + cyclization of ortho-substituted cinnamic esters
Sass, Daiane Cristina,De Lucca Jr., Emílio Carlos,Da Silva Barbosa, Jader,De Oliveira, Kleber Thiago,Constantino, Mauricio Gomes
, p. 5371 - 5374 (2011/10/31)
Conjugate reduction of ortho-substituted cinnamic esters by Stryker's reagent to form copper enolates, followed by intramolecular aldol-type cyclization, successfully generated indane and tetralin rings in one pot efficiently. This tandem reaction is generally diastereoselective and provides good yields.
Unprecedented substoichiometric use of hazardous aryl diazonium salts in the Heck-Matsuda reaction via a double catalytic cycle
Callonnec, Franccois Le,Fouquet, Eric,Felpin, Franccois-Xavier
supporting information; experimental part, p. 2646 - 2649 (2011/06/28)
The first Heck-Matsuda reaction using a catalytic amount of diazonium salts has been discovered. The reaction proceeds through an unprecedented double catalytic cycle in which the electrophile is in situ generated through the reaction advancement. This concept features mild and safe conditions as hazardous aryl diazonium salts are not isolated anymore. Importantly, this sustainable procedure generates only environmentally friendly byproduct such as t-BuOH, H2O, and N2.
Phosphine-free perfluoro-tagged palladium nanoparticles supported on fluorous silica gel: Application to the heck reaction
Bernini, Roberta,Cacchi, Sandro,Fabrizio, Giancarlo,Forte, Giovanni,Niembro, Sandra,Petrucci, Francesco,Pleixats, Roser,Prastaro, Alessandro,Sebastian, Rosa Maria,Soler, Roger,Tristany, Mar,Vallribera, Adelina
, p. 561 - 564 (2008/03/28)
The immobilization of phosphine-free perfluoro-tagged palladium nanoparticles Pd-1 on fluorous silica gel (FSG) and their utilization in the Heck reaction have been investigated. High yields of vinylic substitution products have been obtained. Recycling s
