29555-16-6Relevant academic research and scientific papers
Allylic oxidation of olefins in the presence of Cu-Na-HSZ-320 zeolite as reusable solid catalyst
Carloni,Frullanti,Maggi,Mazzacani,Bigi,Sartori
, p. 8947 - 8950 (2000)
The Cu-Na-HSZ-320 zeolite can be utilised as an efficient and reusable catalyst in the allylic oxidation of olefins with tert-butyl perbenzoate to give the corresponding allylic esters in good yield and excellent selectivity. (C) 2000 Elsevier Science Ltd
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)
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
Metal-free allylic C-H nitrogenation, oxygenation, and carbonation of alkenes by thianthrenation
Du, Hai-Wu,Liu, Ming-Shang,Shu, Wei
, p. 1003 - 1008 (2022/02/02)
Selective functionalization of allylic C-H bonds into other chemical bonds is among the most straightforward and attractive, yet challenging transformations. Herein, a transition-metal-free protocol for direct allylic C-H nitrogenation, oxygenation, and carbonation of alkenes by thianthrenation was developed. This operationally simple protocol allows for the unified allylic C-H amination, esterification, etherification, and arylation of vinyl thianthrenium salts. Notably, the reaction furnishes multialkyl substituted allylic amines, ammonium salts, sulfonyl amides, esters, and ethers in good yields. The reaction proceeds under mild conditions with excellent functional group tolerance and could be applied to late-stage allylation of natural products, drug molecules and peptides with excellent chemoselectivity.
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.
Effective synthesis of bicyclodienes via palladium-catalyzed asymmetric allylic alkylation and ruthenium-catalyzed cycloisomerization
Havare, Nizam
, 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.
Copper-catalyzed oxidative dehydrogenative functionalization of alkanes to allylic esters
Mondal, Rakesh,Chakraborty, Gargi,van Vliet, Kaj M.,van Leest, Nicolaas P.,de Bruin, Bas,Paul, Nanda D.
supporting information, (2019/11/11)
Herein, we report a general, efficient and solvent-free method for the one-pot synthesis of allylic esters via dehydrogenation of unactivated alkanes and subsequent oxidative cross coupling with different substituted carboxylic acids. A simple, well defined and air stable Cu(II)-complex, [Cu(MeTAA)], featuring a tetraaza-macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)) is used as the catalyst. A wide variety of substituted allylic esters were synthesized in high yields starting from readily available starting materials. Control reactions were carried out to understand the reaction sequence and the plausible mechanism.
Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols
Ye, Ke-Yin,Mccallum, Terry,Lin, Song
supporting information, (2019/06/24)
Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely, bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton transfer/electron transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.
Iron-catalyzed esterification of allylic sp3 C–H bonds with carboxylic acids: Facile access to allylic esters
Lu, Bing,Zhu, Fan,Wang, Dan,Sun, Hongmei,Shen, Qi
supporting information, p. 2490 - 2494 (2017/05/31)
The first general and efficient iron-catalyzed esterification of allylic sp3 C–H bonds with carboxylic acids using ionic iron(III) complexes (1–4) as a catalyst and DTBP (DTBP?=?di-tert-butyl peroxide) as an oxidant is achieved. A variety of allylic esters were synthesized in good to excellent yields using the ionic iron(III) complex 2 as a catalyst in a 5?mol% loading. This reaction is characterized by its high efficiency, broad substrate scope with excellent steric hindrance tolerance and good functional group compatibility.
Metal-free, one-pot synthesis of allylic and benzylic esters via decarboxylation and C-H bond activation
Mo, Hanjie,Chen, Dingben,Xu, Lingzhen,Chen, Di,Pan, Fuyou,Yang, Jianguo
supporting information, p. 209 - 215 (2015/05/05)
A tetrabutylammonium iodide catalyzed method has been developed for the one-pot synthesis of allylic and benzylic esters from α-oxo carboxylic acids and alkenes/alkylbenzenes via decarboxylation and C-H bond activation. Various allylic and benzylic esters were obtained in good yield.
