7164-98-9Relevant academic research and scientific papers
A porous metal-organic framework as active catalyst for multiple C-N/C-C bond formation reactions
Wang, Bin,Yang, Pei,Ge, Zhi-Wei,Li, Cheng-Peng
, p. 13 - 15 (2015)
A 3D porous metal-organic framework {[Cu(4-tba)2](solvent)}n (1·S) is assembled via 4-(1H-1,2,4-triazol-1-yl)benzoic acid (Htba) and Cu(II) nodes, which shows the [2 + 2] roto-translational interpenetrating network. Interestingly, 1 displays high CO2 adsorption selectivity over CH4/H2/O2/Ar/N2 gases, and acts an efficient catalyst precursor in some C-N/C-C bond formation reactions, including Chan-Lam coupling reaction of phenylboronic acid with imidazole, Suzuki-Miyoura coupling reaction of phenylboronic acids with aryl halides, and Heck coupling reaction of styrene with aryl halides.
Polymer supported copper(II) amine-imine complexes in the C-N and A3 coupling reactions
Bukowska, Agnieszka,Bukowski, Wiktor,Bester, Karol,Hus, Krzysztof
, (2017)
New polymer supported Cu(II) complexes based on an epoxy functionalized gel type resin were prepared using the multi-stage procedures. The reactions of epoxy groups with ethylenediamine or tris(2-aminoethyl)amine, and then NH2 groups with salic
Base-free anaerobic Cu(II) catalysed aryl-nitrogen bond formations
Van Berkel, Sander S.,Van Den Hoogenband, Adri,Terpstra, Jan Willem,Tromp, Moniek,Van Leeuwen, Piet W.N.M.,Van Strijdonck, Gino P.F.
, p. 7659 - 7662 (2004)
The Cu(II) catalysed coupling of arylboronic acids with imidazole can be performed at ambient temperature without the need for base or dioxygen. The presence of water however is essential for the reaction to proceed.
Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water
Venkateswarlu, Katta,Rao, Kanusu Umamaheswara
, (2021/03/03)
The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H2TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C–N coupling reactions of arylboronic acids and amines (Chan–Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan–Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.
Bis(NHC)-Pd-catalyzed one-pot competitive C-C*C-C, C-C*C-O, C-C*C-N, and C-O*C-N cross-coupling reactions on an aryl di-halide catalyzed by a homogenous basic ionic liquid (TAIm[OH]) under base-free, ligand-free, and solvent-free conditions
Zhu, Yanfang,Xu, Guiyang,Kazemnejadi, Milad
, p. 11662 - 11671 (2021/07/11)
Bis(NHC)-Pd-catalyzed competitive asymmetrical C-C*C-C, C-C*C-O, C-C*C-N, and O-C*C-N cross-coupling reactions were performedviathe one-pot strategy in the presence of a new ionic liquid, which played the roles of solvent, base, and ligand simultaneously. The ionic liquid was prepared based on a methyl imidazolium moiety with hydroxyl counter anionsviaa Hofmann elimination on a 1,3,5-triazine framework (TAIm[OH]). Pd ions could be efficiently coordinated through the bis(NHC)-ligand moiety in the ionic liquid. Based on differences in the competitive kinetics of C-C cross-coupling reactions (Heck, Suzuki, and Sonogashira) with C-N and C-O cross-coupling reactions, and also differences in the kinetics of aryl halides, the coupling reactions could be selectively performed with a low amount of by-products. The competitive cross-coupling reactions were thus performed with high selectivity under mild reaction conditions.
A novel two-dimensional metal-organic framework as a recyclable heterogeneous catalyst for the dehydrogenative oxidation of alcohol and theN-arylation of azole compounds
Liu, Chengxin,Cui, Jin,Wang, Yufang,Zhang, Mingjie
, p. 11739 - 11744 (2021/03/31)
A novel metal-organic framework (MOF) with two-dimensional (2D) crystal structure was developed using Cu(NO3)2·3H2O and 2,2′,5,5′-tetramethoxy-[1,1′-biphenyl]-4,4′-dicarboxylic acid. Further, its structure was characterized using infrared spectroscopy, thermogravimetry, X-ray diffraction, and X-ray crystallography. The activated Cu-MOF was used to catalyze the dehydrogenative oxidation of alcohol andN-arylation of azole compounds. Furthermore, it could be easily recovered and reused.
A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib
Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.
supporting information, p. 5222 - 5229 (2021/07/29)
Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.
Functionalization of superparamagnetic Fe3O4@SiO2 nanoparticles with a Cu(II) binuclear Schiff base complex as an efficient and reusable nanomagnetic catalyst for N-arylation of α-amino acids and nitrogen-containing heterocycles with aryl halides
Sardarian,Kazemnejadi,Esmaeilpour
, (2020/10/20)
Fe3O4@SiO2 nanoparticles was functionalized with a binuclear Schiff base Cu(II)-complex (Fe3O4@SiO2/Schiff base-Cu(II) NPs) and used as an effective magnetic hetereogeneous nanocatalyst for the N-arylation of α-amino acids and nitrogen-containig heterocycles. The catalyst, Fe3O4@SiO2/Schiff base-Cu(II) NPs, was characterized by Fourier transform infrared (FTIR) and ultraviolet-visible (UV-vis) analyses step by step. Size, morphology, and size distribution of the nanocatalyst were studied by transmission electron microscopy (TEM), scanning electron microscopy (SEM), and dynamic light scatterings (DLS) analyses, respectively. The structure of Fe3O4 nanoparticles was checked by X-ray diffraction (XRD) technique. Furthermore, the magnetic properties of the nanocatalyst were investigated by vibrating sample magnetometer (VSM) analysis. Loading content as well as leaching amounts of copper supported by the catalyst was measured by inductive coupled plasma (ICP) analysis. Also, thermal studies of the nanocatalyst was studied by thermal gravimetric analysis (TGA) instrument. X-ray photoelectron spectroscopy (XPS) analysis of the catalyst revealed that the copper sites are in +2 oxidation state. The Fe3O4@SiO2/Schiff base-Cu(II) complex was found to be an effective catalyst for C–N cross-coupling reactions, which high to excellent yields were achieved for α-amino acids as well as N-hetereocyclic compounds. Easy recoverability of the catalyst by an external magnet, reusability up to eight runs without significant loss of activity, and its well stability during the reaction are among the other highlights of this catalyst.
NHC ligand-based half-sandwich iridium complexes: synthesis, structure and catalytic activity in acceptorless dehydrogenation and transfer hydrogenation
Deng, Wei,Jin, Yan,Li, Rong-Jian,Liu, Zhen-Jiang,Wang, Yang,Yao, Zi-Jian
, p. 19002 - 19010 (2021/10/29)
A set of neutral C,C-chelate half-sandwich iridium(iii) complexes have been prepared with NHC ligands that contain pendant aromatic rings as potentially chelating donor sites. The catalytic activity of such iridium complexes has been investigated for the acceptorless dehydrogenation (AD) reactions of alcohols and for the transfer hydrogenation reactions of ketones. The prepared iridium(iii) complexes show excellent catalytic activity for AD reactions of a wide range of secondary alcohols, and they are also shown to be effective for the synthesis of aldehydes from primary alcohols without the observation of undesired byproducts such as esters. Additionally, these complexes are also highly efficient in transfer hydrogenation of ketones and aldehydes, which give the alcohols in good yields under mild conditions. The exact structure and bonding mode of the NHC-based iridium complexes was identified using various spectroscopic methods and single crystal X-ray analysis.
L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols
Ding, Zhiqiang,Nie, Nan,Chen, Tian,Meng, Lingxin,Wang, Gongshu,Chen, Zhangpei,Hu, Jianshe
supporting information, (2020/12/21)
A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield.
