20883-96-9Relevant academic research and scientific papers
Synthesis of functionalized benzothiophenes by twofold Heck and subsequent 6π-electrocyclization reactions of 2,3-dibromothiophene
Toguem, Serge-Mithérand Tengho,Hussain, Munawar,Malik, Imran,Villinger, Alexander,Langer, Peter
, p. 4962 - 4964 (2009)
The Heck reaction of 2,3-dibromothiophene afforded 2,3-di(alkenyl)thiophenes which were transformed into benzothiophenes by domino ′6π-electrocyclization/dehydrogenation′ reactions.
Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide
Ojha, Subhadra,Panda, Niranjan
supporting information, p. 1292 - 1298 (2022/02/19)
A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is
Pd salen complex@CPGO as a convenient, effective heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions
Ghabdian, Mahdieh,Nasseri, Mohammad Ali,Allahresani, Ali,Motavallizadehkakhky, Alireza
, p. 1713 - 1728 (2018/05/25)
A Pd(II) Schiff base complex supported on graphene oxide nanosheets (Pd(II) salen@CPGO) has been synthesized and characterized by FT-IR, ICP-AES, XRD, SEM/EDX and TEM. The synthesized nanocatalyst has been found to be an efficient heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki coupling reactions. Pd(II) salen@CPGO could be separated and recovered easily from the reaction mixture and recycled several times without a discernible decrease in its catalytic activity. The construction of a solid sheet-supported Pd catalyst would be expected to be a promising system to perform heterogeneous catalytic reactions.
Pd nanoparticles supported on reduced graphene oxide as an effective and reusable heterogeneous catalyst for the Mizoroki–Heck coupling reaction
Mirza-Aghayan, Maryam,Mohammadi, Marzieh,Addad, Ahmed,Boukherroub, Rabah
, (2020/02/05)
A general method for the synthesis of palladium nanoparticles loaded on reduced graphene oxide functionalized with diethylenetriamine (PdNPs/rGO-NH2) using a sonochemical procedure is described. The heterogeneous nanocomposite was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, energy dispersive X-ray, thermogravimetric analysis, high-angle annular dark field scanning transmission electron microscopy, X-ray photoelectron spectroscopy, UV–visible absorption, and inductively coupled plasma optical emission spectrometry. The PdNPs/rGO-NH2 was very effective for the Mizoroki–Heck coupling reaction of several aryl iodide compounds with different alkenes in the presence of triethylamine. The reaction provides the coupling products in good to excellent yields (59–100%). Additionally, the PdNPs/rGO-NH2 catalyst can be reutilized for six successive runs without any apparent diminution of its catalytic reactivity.
Organoselenium-palladium(ii) complex immobilized on functionalized magnetic nanoparticles as a promising retrievable nanocatalyst for the "phosphine-free" Heck-Mizoroki coupling reaction
Rangraz, Yalda,Nemati, Firouzeh,Elhampour, Ali
, p. 15361 - 15371 (2018/09/29)
In the present study, for the first time, an air- and moisture-stable organoselenium-palladium complex immobilized on silica-coated magnetic nanoparticles was designed, synthesized and applied as a practical and retrievable catalyst in organic synthesis. The chemical nature and structure of this novel catalytic system were characterized using various techniques such as Fourier transform infrared (FT-IR) spectroscopy, X-ray powder diffraction (XRD), X-ray photoelectron spectroscopy (XPS), thermogravimetric analysis (TGA), transmission electron microscopy (TEM), field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) spectroscopy and vibrating sample magnetometry (VSM). Subsequently, the catalytic performance of the synthesized nanocatalyst was investigated in the Heck-Mizoroki cross-coupling reaction and excellent results are obtained. The low catalyst loading, wide substrate scope, high yield, short reaction time, simple separation from the reaction mixture and importantly, the longevity of the nanocatalyst for at least five successive recycles without significant degradation in its activity are the main merits of this protocol. Above all, this work opens up attractive and interesting routes for the use of organoselenium compounds as efficient ligands for the synthesis of heterogeneous catalysts.
Novel cyclodextrin-modified h-BN@Pd(II) nanomaterial: An efficient and recoverable catalyst for ligand-free C-C cross-coupling reactions in water
Ma, Xiaojun,Lv, Guanghui,Cheng, Xu,Li, Weijian,Sang, Rui,Zhang, Yong,Wang, Qiantao,Hai, Li,Wu, Yong
, (2017/10/05)
An environmentally friendly palladium(II) catalyst supported on cyclodextrin-modified h-BN was successfully prepared. The catalyst was characterized by FT-IR, SEM, TG, XRD and XPS, and the loading level of Pd in h-BN@β-CD@Pd(II) was measured to be 0.088?mmol g?1 by ICP. It exhibits excellent catalytic activity for the Suzuki and Heck reactions in water, and can be easily separated and consecutively reused for at least nine times. In addition, a series of pharmacologically interesting products were successfully synthesized using this catalyst to demonstrate its potential applications in pharmaceutical industries. Above all, this work opens up an interesting and attractive avenue for the use of cyclodextrin-functionalized h-BN as an efficient support for hydrophilic heterogeneous catalysts.
Thiophene Methanimine–Palladium Schiff Base Complex Anchored on Magnetic Nanoparticles: A Novel, Highly Efficient and Recoverable Nanocatalyst for Cross-Coupling Reactions in Mild and Aqueous Media: Γ-Fe2O3/AEPH2-TC-Pd Catalyzed Suzuki–Miyaura and Heck–Mizoroki Reactions
Jahanshahi, Roya,Akhlaghinia, Batool
, p. 2640 - 2655 (2017/09/06)
Abstract: In this study, a novel thiophene methanimine–palladium Schiff base complex anchored on decorated γ-Fe2O3 with 2-aminoethyl dihydrogen phosphate (γ-Fe2O3/AEPH2-TC-Pd) was synthesized as a new magnetically separable nanocatalyst. Characterization of the new designed nanocatalyst was performed successfully using different techniques such as FT-IR, XRD, XPS, TEM, TGA, VSM, ICP and elemental analysis. This nanocatalyst presented a superb catalytic activity for Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions. The most important features of the prepared catalytic system which makes the current protocol more beneficial from both industrial and environmental viewpoints are its ease of recovery and reusability up to nine cycles without appreciable loss of the catalytic performance, as well as accomplishing the reactions under mild conditions in aqueous media which is a great challenge in some cross-coupling reactions. Graphical Abstract: [Figure not available: see fulltext.].
Aminophosphine Palladium(0) Complex Supported on ZrO2 Nanoparticles (ZrO2@AEPH2-PPh2-Pd(0)) as an Efficient Heterogeneous Catalyst for Suzuki–Miyaura and Heck–Mizoroki Reactions in Green Media
Razavi, Nasrin,Akhlaghinia, Batool,Jahanshahi, Roya
, p. 360 - 373 (2017/02/18)
Abstract: A new aminophosphine palladium(0) complex supported on ZrO2nanoparticles (ZrO2@AEPH2-PPh2-Pd(0)) was successfully synthesized and characterized using FT-IR, XRD, XPS, SEM, TEM, EDS, TGA and ICP techniques. Characterization results revealed that the synthesized catalyst had tetragonal and monoclinic structure with spherical morphology. The prepared nanocatalyst was showed excellent reactivity in the Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions. Moreover, this nanocatalyst can be easily recovered and reused for at least six cycles without deterioration in catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
Ligand-Free C–C Coupling Reactions Promoted by Hexagonal Boron Nitride-Supported Palladium(II) Catalyst in Water
Cheng, Xu,Li, Weijian,Nie, Ruifang,Ma, Xiaojun,Sang, Rui,Guo, Li,Wu, Yong
supporting information, p. 454 - 466 (2017/02/10)
A micron-scale palladium(II) material has been successfully prepared using Schiff base-modified hexagonal boron nitride as a support and used for the first time as an efficient and recyclable catalyst in organic synthesis. The morphology, composition, metal loading and thermal stability of the catalyst were studied using scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS), X-ray diffraction (XRD), infrared spectroscopy (FT-IR), inductively coupled plasma (ICP) and thermogravimetric (TG) analyses. Then, the micron material was tested in various C–C cross-coupling reactions and exhibited excellent catalytic activities in the Suzuki and Heck reactions. Moreover, the catalyst could be easily recovered by simple filtration and reused at least ten times without significant loss of its catalytic activity. In general, this work demonstrates the possibility of using Schiff-base@hexagonal boron nitride as an efficient support for heterogeneous catalysts. (Figure presented.).
Flexible, dicationic imidazolium salts for in situ application in palladium-catalysed Mizoroki–Heck coupling of acrylates under aerobic conditions
Milton, Marilyn Daisy,Garg, Parul
, p. 759 - 766 (2016/09/04)
The synthesis, characterization and in situ catalytic performance of new unsymmetric N,N′-disubstituted imidazolium-based dicationic salts in Mizoroki–Heck coupling of acrylates with aryl bromides under aerobic conditions are described. A series of flexible dicationic salts with varying steric and electronic properties were synthesized in good to excellent yields. All the salts were well characterized using spectroscopic techniques. X-ray diffraction analysis of two salts with the same dicationic backbone and different counter anions shows that the ligand adopts two different conformations which are influenced by the nature of the anion. Thus, the ligand is capable of changing its conformation according to the change in environment due to its flexible nature. All the synthesized imidazolium salts were found to be active in in situ palladium-catalysed Mizoroki–Heck coupling under aerobic conditions. Amongst the salts, the hydroxyl-functionalized imidazolium salt, incorporating the features of both bidentate chelating O,O ligand and carbene, shows the maximum catalytic activity. A variety of aryl and heteroaryl methyl and ethyl cinnamates were synthesized using these imidazolium salts as preligands. In addition, NMR studies confirm in situ generation of normal N-heterocyclic carbenes from the C-2 position of imidazol-2-ylidene ring. The mercury poisoning test was also performed to ascertain the nature of catalytically active palladium species. Aerobic conditions, low catalytic loading (0.5?mol%), shorter reaction times, broad functional group tolerance and good to excellent isolated yields are some of the significant features of the novel catalytic systems described here. Copyright
