16176-77-5Relevant academic research and scientific papers
Preparation method of N-arylindole under copper catalysis
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Paragraph 0048-0061; 0064-0066, (2021/07/08)
The invention provides a preparation method of N-arylindole under copper catalysis. The preparation method comprises the following steps: S1, selecting a proper amount of a reaction reagent, a catalyst, a solvent and the like; S2, sequentially adding the
N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst
Dindarloo Inaloo, Iman,Majnooni, Sahar,Eslahi, Hassan,Esmaeilpour, Mohsen
, p. 13266 - 13278 (2020/10/07)
An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is
Nickel-Catalyzed Mizoroki-Heck/Amination Cascade Reactions of o-Dihaloarenes with Allylamines: Synthesis of Indoles
Chen, Xu,Lin, Jin,Wang, Biao,Tian, Xu
supporting information, p. 7704 - 7708 (2020/10/12)
An efficient Mizoroki-Heck/amination cascade reaction of o-dihaloarenes with allylamines has been developed using nickel and IPr carbene ligand as catalyst. This protocol enables the synthesis of a broad range of substituted indoles by a cascade process, from readily available starting materials. Mechanistic studies suggest that the Mizoroki-Heck reaction occurred first under IPr-nickel catalysis.
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.
L-Arginine as a base and ligand for the palladium-catalyzed C-C and C-N cross-coupling reactions in aqueous media
Veisi, Hojat,Mohammadi Biabri, Parisa,Falahi, Homeyra
, p. 3482 - 3486 (2017/08/10)
L-Arginine (2-amino-5-guanidinopentanoic acid) acts as a base and ligand in reaction medium, exhibits a very high activity and recyclability to palladium-catalyzed C-C and C-N cross-coupling reactions in aqueous media. The corresponding Suzuki products were obtained in good to excellent yields by using various aryl halides (I, Br, Cl). Also, the cross coupling reactions of arylboronic acids with various amines in aqueous medium proceed in good to excellent yield under same conditions. Furthermore, the catalyst could be easily separated from the reaction mixture and could be recycled several times without significant loss in its catalytic activity.
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.
Utilizing Mor-DalPhos/palladium-catalyzed monoarylation in the multicomponent one-pot synthesis of indoles
Rotta-Loria, Nicolas L.,Borzenko, Andrey,Alsabeh, Pamela G.,Lavery, Christopher B.,Stradiotto, Mark
, p. 100 - 106 (2015/01/30)
The application of a Mor-DalPhos/palladium catalyst system in the one-pot, multicomponent assembly of substituted indoles from ortho-chlorohaloarenes, alkyl ketones (including acetone), and primary amines is reported. The described protocols offer improved substrate scope in all three reaction components, under more mild conditions and without the need for an additional drying agent. Also reported are the first examples of such multicomponent reactions where all reactants are combined at the start of the reaction, without the need for inert atmosphere reaction conditions.
Copper nanoparticle decorated organically modified montmorillonite (OMMT): An efficient catalyst for the N-arylation of indoles and similar heterocycles
Talukdar, Dhrubajyoti,Das, Gautam,Thakur, Suman,Karak, Niranjan,Thakur, Ashim J.
, p. 238 - 243 (2015/02/19)
A highly active ligand-free and efficient copper nanoparticle decorated OMMT catalyzed N-arylation of NH-heterocycles, i.e. indole, imidazole, benzimidazole, pyrrole, carbazole has been demonstrated.
C-N coupling of indoles and carbazoles with aromatic chlorides catalyzed by a single-component NHC-nickel(0) precursor
Rull, Silvia G.,Blandez, Juan F.,Fructos, Manuel R.,Belderrain, Tomás R.,Nicasio, M. Carmen
supporting information, p. 907 - 911 (2015/03/30)
A new and efficient nickel-based protocol for the N-arylation of indoles and carbazoles with aromatic chlorides, the least expensive of the aryl halides, is described. The procedure provides selectively N-(hetero)arylation products in good to high yields, in short reaction times and without adding an excess of ligands.
Indoles synthesized from amines via copper catalysis
Besandre, Ronald,Jaimes, Miguel,May, Jeremy A.
supporting information, p. 1666 - 1669 (2013/06/26)
N-Substituted indoles are synthesized from primary amines through a tandem reaction sequence. Initial condensation of the amine with an α-(o-haloaryl)ketone or aldehyde is followed by intramolecular aryl amination catalyzed by CuI. A variety of anilines and alkyl amines, including those with significant steric demands, are converted to indoles in high yields and with varying indole substitution.
