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A new N,N-dimethyl-D-glucosamine ligand has been developed for the copper-catalyzed Ullmann-type coupling of N-H heterocycles (e.g., indoles, benzimidazoles, pyrazoles and triazoles) with aryl halides. This method was accomplished not only featuring excellent yields, mild reaction conditions and simple operation, but also showing eco-friendly and broad-spectrum substrates, and could be widely used in the construction of N-aryl heterocyclic systems.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 16096-33-6, molcular formula is C14H11N, introducing its new discovery. Application In Synthesis of 1-Phenyl-1H-indole

A series of palladium complexes, [PdCl(L1-4)] (1-4) (L1 = 9,10-phenanthrenequinone thiosemicarbazone, L2 = 9,10-phenanthrenequinone methylthiosemicarbazone, L3 = 9,10-phenanthrenequinone phenylthiosemicarbazone, and L4 = 9,10-phenanthrenequinone semicarbazone), have been synthesized and characterized by elemental analyses, UV-vis, FT-IR, 1H and 13C NMR, and ESI-Mass spectroscopic methods. The catalytic efficiency of the synthesized complexes was examined against N-arylation of imidazole. The system works well with the electron-rich, -neutral, and -deficient aryl halides to afford the products in good to excellent yields. Sterically congested aryl halides and heteroaryl halides have also been used as substrates to provide N-arylated heterocycles. In addition, this methodology can be applicable to other substrates with N-containing heterocycles.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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This research provides a straightforward understanding of the regioselective palladation of indole derivatives by capturing both C2-Pd and C3-Pd intermediates of N-phenylindole and N-methylindole. Those tetranuclear indolyl palladacycles suggest that the regioselectivity of palladation depends on the N-substituted protective groups of indoles as well as the acidity of the reaction medium.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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(Chemical Equation Presented) A practical and promising protocol was developed for N-arylations of various amines with differently substituted aryl halides. The processes are efficiently promoted by the catalyst system involving the environmentally benign Fe2O3 and the universal ligand L-proline. The versatility, convenient operation, low cost, and environmental friendliness, in combination with the high yields, render this method viable for use in both laboratory research and larger industrial scales.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Ph3SnCl is introduced as a very suitable source of phenyl group for coupling with phenols, amines, and thiols in the presence of Cu(OAc)2 in Et3N at room temperature to give aryl ethers, amines, and arylthio ethers in high yields. In addition, the application of Ph3SnCl in the Stille coupling of aryl halides in the presence of Pd(0) catalyst in PEG 400 at 110C is discussed.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Extracurricular laboratory:new discovery of 1-Phenyl-1H-indole

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A new, efficient and recyclable lanthanum(III) oxide-catalyzed C-N cross-coupling

A new and efficient protocol for the C-N cross-coupling of aryl halides with heteroaromatic amines in the presence of lanthanum(III) oxide (10 mol%) as a recyclable catalyst, N,N?-dimethylethylenediamine (DMEDA) (20 mol%) and potassium hydroxide (KOH) as a base in dimethyl sulfoxide (DMSO) at 110 C has been developed. This inexpensive catalytic system is highly effective towards the amination of aryl halides with various nitrogen nucleophiles and is significantly tolerant towards other functional groups in the substrates. Copyright

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 16096-33-6, molcular formula is C14H11N, introducing its new discovery. HPLC of Formula: C14H11N

NITROGEN-CONTAINING MONODENTATE PHOSPHINES AND THEIR USE IN CATALYSIS

The present invention relates to novel nitrogen-containing monodentate phosphane ligands of formula (I) and to their use in catalytic reactions, especially in the improvement of haloaromatic compounds.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile

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.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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METAL COMPLEX COMPRISING AMIDINE AND INDOLE FUSED CYCLOPENTADIENYL LIGANDS

A metal complex of the formula (1) InCyLMZp (1), wherein M is a group 4 metal Z is an anionic ligand, p is number of 1 to 2, preferably 2, InCy is an indole fused cyclopentadienyl-type ligand of the formula (2) wherein R1 means for each index m individually a C1-C4-alkyl that substitutes a hydrogen atom of the benzene ring, m is a number of 0 to 4, preferably 0 to 2, in particular 0, R2 means C1-C10-alkyl, C5- C10-cycloalkyl, and an unsubstituted or C1-C10-alkyl or C1-C4-dialkyl amino substituted C6-C10-aryl, in particular C1-C4-20 alkyl substituted phenyl, more preferably methyl, phenyl or di-C1-C4-alkyl substituted phenyl, in particular di-tert.-butyl-phenyl, R3, R4 and R5 being individually selected from the group of hydrogen, C1-C4-alkyl, unsubstituted or C1-C4-alkyl and/or halogen, in particular chlorine or fluorine substituted C6-C10-aryl, in particular unsubstituted or C1-C4-alkyl substituted phenyl whereby preferably R3, R4 and R5 being individually selected from the group of hydrogen, C1-C4-alkyl, unsubstituted or C1-C4-alkyl and/or halogen, in particular chlorine or fluorine substituted C6-C10-aryl, in particular C1-C4-alkyl substituted phenyl, more preferably at least one of the radicals R3 to R5 shall mean C1-C4-alkyl, in particular methyl, i-propyl and phenyl and, L is an amidinate ligand of the formula (3) (3) wherein the amidine-containing ligand is covalently bonded to the metal M via the imine nitrogen atom, and Sub1 is an unsubstituted or C1-C4-alkyl and/or halogen, in particular chlorine or fluorine substituted C6-C10-aromatic substituent, in particular phenyl and Sub2 is a substituent comprising a heteroatom of group 15, through which Sub2 is bonded to the imine carbon atom or Sub1 and Sub2 together with the imino group they are connected to form a ligand of formula (3a) wherein the amidine-containing ligand (3a) is covalently bonded to the metal M via the imine nitrogen atom N2, wherein the benzo ring fused to the amidine ring may be unsubstituted or contain further substituents R7, which are individually of the index “q” selected from the group of hydrogen, C1-C4-alkyl and halogen and whereby q is a number of 0 to 4, preferably 0 to 2, most preferably 0, Sub4 is an aliphatic or aromatic cyclic or linear substituent comprising a group 14 atom through which Sub4 is bonded to the amino nitrogen atom N 1, preferably Sub4 is a C6-C10-aromatic ring, preferably phenyl which is unsubstituted or substituted by one or more substituents from the group selected from halogen, in particular Cl or F and C1-C4-alkyl, preferably Sub4 is a 2,6-di-fluorophenyl.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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2,6-Bis(2-methylhydrazine-1-carbonyl)pyridine 1-oxide as an Efficient Ligand for Copper-Catalyzed C?N Coupling Reaction in Water

Abstract: Cu2O/2,6-bis(2-methylhydrazine-1-carbonyl)pyridine 1-oxide was found to be an efficiently catalytic system for the N-arylation of imidazole, indole, benzimidazole, pyrrole, benzylamine and ethanolamine with aryl iodides and bromides by using NaOH as base in the presence of 20?mol% (n-Bu)4NBr, and water as solvent at 130?C in 24?h, and giving the N-arylated products in moderate to excellent yields.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles