3352-93-0Relevant academic research and scientific papers
A simple route to methyl 5S-(benzoyloxy)-6-oxohexanoate, a key intermediate in leukotriene synthesis
Hayes, Roy,Wallace, Timothy W.
, p. 3355 - 3356 (1990)
Methyl 5S-(benzoyloxy)-6-oxohexanoate 2, an intermediate in synthetic routes to the lipoxygenase-derived arachidonic acid metabolite leukotriene B4, is available in three steps from 2-cyclohexen-1-one, using Schreiber's unsymmetrical ozonolysis protocol.
Synthesis of chiral 2,2′-dipyridylamines and their use in the copper-catalyzed asymmetric allylic oxidation of cyclohexene
Bolm, Carsten,Frison, Jean-Cédric,Le Paih, Jacques,Moessner, Christian
, p. 5019 - 5021 (2004)
Chiral dipyridylamines have been synthesized by N-arylation reactions, and the applicability of those compounds to the copper-catalyzed asymmetric allylic oxidation of cyclohexene was demonstrated.
A new dimeric copper(II) complex of hexyl bis(pyrazolyl)acetate ligand as an efficient catalyst for allylic oxidations
Bagnarelli, Luca,Dolmella, Alessandro,Gabrielli, Serena,Giacomantonio, Roberto,Pellei, Maura,Santini, Carlo,Vallesi, Riccardo
, (2021/12/14)
A new dimeric copper(II) bromide complex, [Cu(LOHex)Br(μ-Br)]2 (1), was prepared by a reaction of CuBr2 with the hexyl bis(pyrazol-1-yl)acetate ligand (LOHex) in acetonitrile solution and fully characterized in
Copper porphyrin-catalyzed cross dehydrogenative coupling of alkanes with carboxylic acids: Esterification and decarboxylation dual pathway
Chen, Xiao-Yan,Yang, Shuang,Ren, Bao-Ping,Shi, Lei,Lin, Dong-Zi,Zhang, Hao,Liu, Hai-Yang
, (2021/08/13)
A dual-functional copper porphyrin-catalyzed cross dehydrogenative coupling (CDC) of carboxylic acids with alkanes was reported firstly. The reaction gives allylic esters or alkylalkenes depending on the carboxylic acid substrates. Copper porphyrin catalyzed CDC method has the superiority of short reaction time, good functional group tolerance, base and solvent free, producing target products in an atom-economic manner.
Copper-iron mixed oxide supported onto cordierite honeycomb as a heterogeneous catalyst in the Kharasch-Sosnovsky oxidation of cyclohexene
Fellak, M. Amine,Gatica, José M.,Guerra, Francisco M.,Moreno-Dorado, F. Javier,Vidal, Hilario,Yeste, M. Pilar
, (2021/11/10)
A copper-iron mixed oxide was deposited by the washcoating procedure over cordierite honeycomb monoliths for its use as a heterogeneous catalyst in organic synthesis processes. In particular, the prepared catalyst, characterized by techniques such as X-ra
Immobilization of (l)-valine and (l)-valinol on SBA-15 nanoporous silica and their application as chiral heterogeneous ligands in the Cu-catalyzed asymmetric allylic oxidation of alkenes
Ashouri, Akram,Mahramasrar, Mahsa,Majidian, Shiva,Rashid, Hersh I,Samadi, Saadi
supporting information, p. 17630 - 17641 (2021/10/04)
SBA-15 nanoporous silica was synthesized by hydrothermal method using P123 surfactant and tetraethoxyortosilicate in acidic condition and then functionalized by 3-chloropropyltrimethoxysilane. Next, by immobilization of chiral amino acid (S)-2-amino-3-methyl butanoic acid (l-valine) and chiral amino alcohol (S)-2-amino-3-methylbutane-1-ol (l-valinol), preparedviathe reduction ofl-valine by NaBH4/I2in THF, on functionalized-SBA-15, chiral heterogeneous ligands AL*-i-Pr-SBA-15 and AA*-i-Pr-SBA-15 were prepared and characterized by FT-IR, XRD, TGA, EDX, SEM, BET-BJH techniques. The asymmetric allylic oxidation of alkenes was done using copper-complexes of these ligands and the as-synthesized peresters. The reactions were optimized by varying various parameters such as temperature, solvent, amount of chiral heterogeneous ligand, as well as the type and amount of copper salt. Under optimized conditions, 6 mg of AL*-i-Pr-SBA-15 and 3.2 mol% of Cu(CH3CN)4PF6in acetonitrile at 50 °C, the chiral allylic ester was obtained with 80% yield and 39% enantiomeric excess in 24 h. The recyclability of the chiral heterogeneous catalysts was also evaluated without significant reduction in the reaction results up to three runs.
Allyl coupling reaction method and application thereof
-
Paragraph 0232-0237, (2021/08/25)
The invention discloses a novel allyl coupling reaction method which takes an allyl thianthene salt as an allylation reagent and respectively takes a carboxylic acid compound. An allylated coupling product is obtained by reacting a substrate with a base in the presence of a base, or directly with a carboxylate compound, an aromatic hydrocarbon/heterocyclic hydrocarbon as a substrate, and at room temperature. The preparation method is mild in condition and free of transition metal participation, can efficiently realize preparation of various allyl ester, allyl substituted amine and allyl substituted aromatic hydrocarbon/heterocyclic hydrocarbon compound, and has an ideal application prospect in the fields of fine chemical engineering, material science and pharmacy.
Development of new and efficient copper(ii) complexes of hexyl bis(pyrazolyl)acetate ligands as catalysts for allylic oxidation
Gabrielli, Serena,Pellei, Maura,Venditti, Iole,Fratoddi, Ilaria,Battocchio, Chiara,Iucci, Giovanna,Schiesaro, Irene,Meneghini, Carlo,Palmieri, Alessandro,Marcantoni, Enrico,Bagnarelli, Luca,Vallesi, Riccardo,Santini, Carlo
, p. 15622 - 15632 (2020/11/24)
In this study, two new hexyl bis(pyrazol-1-yl)acetate ligands and related copper(ii) complexes were prepared and fully characterized in the solid state and in solution. Their electronic and molecular structures were investigated by X-ray photoelectron spe
2-Aminopyrazine-functionalized MCM-41 nanoporous silica as a new efficient heterogeneous ligand for Cu-catalyzed allylic C–H bonds oxidation of olefins
Samadi, Saadi,Ashouri, Akram,Kamangar, Shadi,Pourakbari, Fatemeh
, p. 557 - 569 (2019/11/03)
In spite of the importance of the application of allylic C–H bond oxidation of olefins in organic synthesis and existence of the numerous reports, lots of limitations such as large excess of the olefin respect to the oxidant, low chemical yield, long time of reaction and a large amount of the catalyst were reminded. We introduced a novel catalytic system using functionalized MCM-41 as catalyst support to promote efficiency of this reaction. The heterogeneous ligand Pyr-MCM-41 was prepared by substituted 2-aminopyrazine ligand on functionalized MCM-41 with 3-chloropropyltrimthoxysilane and characterized by FT-IR, XRD, SEM, EDX, BET, TGA, CHN techniques. In situ immobilized Pyr-MCM-41 by copper (I) trifluoromethanesulfonate (CuOTf) was applied in direct catalytic esterification of inert C–H bonds in olefins using various peresters at room temperature.
Effective synthesis of bicyclodienes via palladium-catalyzed asymmetric allylic alkylation and ruthenium-catalyzed cycloisomerization
Havare, Nizam
supporting information, p. 1445 - 1462 (2021/01/05)
[n.3.0]Bicycles (n = 3-6) can be synthesized using palladium-catalyzed asymmetric allylic alkylation followed by rutheniumcatalyzedcycloisomerization.Newtypesoftriarylphosphino-1,2-diaminooxazolineligandsshowthesamehighlevelsofenantioselectivity observed with Trost ligand when employed in Pd-catalyzed allylic alkylation reactions. The enyne products of these allylic alkylation reactions were further elaborated using a Ru-catalyzed redox isomerization process, for which a mechanism is proposed.
