210162-61-1Relevant articles and documents
Exploration of Catalytic Activity of Quercetin Mediated Hydrothermally Synthesized NiO Nanoparticles Towards C–N Coupling of Nitrogen Heterocycles
Krishnaveni,Lakshmi,Kadirvelu,Kaveri
, p. 1628 - 1640 (2019/12/24)
Abstract: A new approach towards the preparation of phase pure NiO nanoparticles via quercetin mediated hydrothermal method is proposed in this work. The performance of quercetin as capping agent is found to be good. The XRD and SEM results confirm that the NiO nanoparticles prepared with quercetin are smaller in size and have refined morphology than that prepared without quercetin. Thermal stability, elemental composition and particle size of prepared nanoparticles have been revealed by TG-DSC, EDAX and HR-TEM analysis respectively. N2 adsorption–desorption isotherm (BET) analysis was done to reveal specific surface area. The prepared NiO nanoparticles act as cost effective, environmental friendly and efficient catalyst for the C–N cross coupling of indole and electron deficient pyrrole, under very mild reaction conditions. The catalytic system is able to tolerate many functional groups with different electronic and structural properties. Hence the present catalytic system may be possibly applied in large scale synthesis. Graphic Abstract: [Figure not available: see fulltext.].
Copper-Catalyzed Decarboxylative N -Arylation of Indole-2-carboxylic Acids
Zhang, Yan,Hu, Zhe-Yao,Li, Xin-Chang,Guo, Xun-Xiang
, p. 1803 - 1808 (2019/04/05)
A novel decarboxylative N -arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu 2 O as the catalyst to give the corresponding N -aryl indoles in high yields. This synthet
Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile
Hock, Katharina J.,Knorrscheidt, Anja,Hommelsheim, Renè,Ho, Junming,Weissenborn, Martin J.,Koenigs, Rene M.
supporting information, p. 3630 - 3634 (2019/02/13)
The functionalization of C?H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C?H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.
Iron oxide encapsulated by copper-Apatite: An efficient magnetic nanocatalyst for: N-Arylation of imidazole with boronic acid
Amadine, Othmane,Essamlali, Younes,Amedlous, Abdallah,Zahouily, Mohamed
, p. 36471 - 36478 (2019/11/20)
N-Arylation of imidazole was carried out with various arylboronic acids on iron oxide encapsulated by copper-Apatite (Fe3O4?Cu-Apatite), producing excellent yields. Firstly, the iron nanoparticles were prepared using a solvothermal m
Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides
Chen, Ji,Wu, Jimmy
supporting information, p. 3951 - 3955 (2017/03/27)
We report an unprecedented transition metal-free coupling of indoles with aryl halides. The reaction is promoted by KOtBu and is regioselective for C3 over N. The use of degassed solvents devoid of oxygen is necessary for the success of the transformation. Preliminary studies implicate a hybrid mechanism that involves both aryne intermediates and non-propagative radical processes. Electron transfer is also a distinct possibility. These conclusions were substantiated by EPR data, isotopic labeling studies, and the use of radical scavengers and electron transfer inhibitors.
Copper(I) Oxide/N,N′-Bis[(2-furyl)methyl]oxalamide-Catalyzed Coupling of (Hetero)aryl Halides and Nitrogen Heterocycles at Low Catalytic Loading
Pawar, Govind Goroba,Wu, Haibo,De, Subhadip,Ma, Dawei
supporting information, p. 1631 - 1636 (2017/05/22)
An easily prepared oxalic diamide is a powerful ligand for the copper-catalyzed coupling of aryl halides with nitrogen heterocycles. Only 1–2 mol% each of copper(I) oxide and N,N′-bis[(2-furyl)methyl]oxalamide (BFMO) are needed to form N-arylation products under mild conditions. More than 10 different types of nitrogen heterocycles are compatible with these conditions, thereby giving the corresponding N-arylation products. (Figure presented.).
A carbon nitride supported copper nanoparticle composite: a heterogeneous catalyst for the N-arylation of hetero-aromatic compounds
Nandi, Debkumar,Siwal, Samarjeet,Mallick, Kaushik
supporting information, p. 3082 - 3088 (2017/04/14)
A graphitic carbon nitride supported copper nanoparticle composite (Cu-gCN) has been found to be an active catalyst for the N-arylation of hetero-aromatic systems (pyrrole, pyrazole, and substituted indole) and benzamide molecules, with high product selectivity and good to excellent yields, using substituted aryl bromide as a coupling partner. The intercalated structure and the amine functional group of the carbon nitride prevent the aggregation of the catalytically active copper species during the reaction, and the recyclability study shows the stable performance of the catalyst without a significant loss of catalytic activity.
Immobilized Pd nanoparticles on silica-starch substrate (PNP-SSS): Efficient heterogeneous catalyst in Buchwald–Hartwig C–N cross coupling reaction
Panahi, Farhad,Daneshgar, Fatemeh,Haghighi, Fatemeh,Khalafi-Nezhad, Ali
, p. 210 - 217 (2017/10/09)
An immobilized Pd nanoparticle on silica-starch substrate (PNP-SSS) is introduced as an efficient heterogeneous catalyst in Pd-catalyzed Buchwald–Hartwig C–N cross coupling reaction. A range of aryl amines were synthesized using reaction of aryl halides (chloride, bromide and iodide) and amines using PNP-SSS catalyst in good to excellent yields. The PNP-SSS catalyst shows high catalytic activity in C-N bond formation reaction and it is reusable in this reaction at least for five times without significant decreasing in its catalytic activity.
Immobilized Pd(0) nanoparticles on phosphine-functionalized graphene as a highly active catalyst for Heck, Suzuki and N-arylation reactions
Fareghi-Alamdari, Reza,Haqiqi, Mohsen G.,Zekri, Negar
, p. 1287 - 1296 (2016/02/19)
In this study, a phosphine group was chemically grafted to the surface of graphene in order to prepare a reusable ligand with high surface area, incorporating a phosphine moiety. The treatment of graphene oxide (GO) with hydroxide followed by an aqueous work-up yields an OH-functionalized graphene material (GOH) via ring-opening of the epoxide groups. Reaction of GOH with chlorodiphenylphosphine (ClPPh2) gives a new material, GOPPh2 (PFG), which can be used for stabilization of metal nanoparticles or complexation of transition metals in order to prepare a reusable metal catalyst. Stabilization of palladium nanoparticles on the surface of GOPPh2 resulted in the production of an efficient heterogeneous Pd catalyst (PFG-Pd) for application in C-C and C-N bond formation reactions. The PFG-Pd catalyst was characterized using some different microscopic and spectroscopic techniques such as FT-IR, XRD, TEM, SEM, EDX, and ICP analysis. The applicability of the PFG-Pd catalyst was evaluated in Heck, Suzuki and N-arylation reactions. The catalyst system showed high catalyst activity in these processes and the target products were obtained in high isolated yields. The PFG-Pd catalyst was reusable in these reactions for at least 5 times with no significant decrease in its catalytic activity.
SBA-15 Immobilized Phenanthroline-Copper(I) Complex as a Recyclable Efficient Catalyst for N-Arylation of Amides and N-H Heterocycles with Aryl Halides
Hosseinzadeh, Rahman,Aghili, Nora,Tajbakhsh, Mahmood
, p. 193 - 203 (2016/03/12)
5-(N,N-bis-3-(triethoxysilyl) propyl) ureyl-1,10-phenanthroline was prepared and successively grafted onto mesoporous silica of SBA-15 to get SBA-15 anchored ligand which was then reacted with Cu(I) to get SBA-15 anchored complex as the heterogeneous copper catalyst. This catalyst was characterized by FT-IR, XRD, CHN, AAS, TGA, EDAX, BET, SEM and TEM. The activities of the catalyst were tested in C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. The catalyst showed high catalytic activities for these cross-coupling reactions providing good to excellent yields of desired products. Moreover, the catalyst can be easily recovered by simple filtration and reused several times without significant loss of its catalytic activity.
