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Upstream product

• 83-34-1 3-Methylindole 
• 350-46-9 4-Fluoronitrobenzene 
• 36797-43-0 3-methyl-N-(p-toluenesulfonyl)indole 
• 636-98-6 p-nitrobenzene iodide 
• 100-00-5 4-chlorobenzonitrile 
• 586-78-7 para-nitrophenyl bromide 

Relevant academic research and scientific papers

Base-promoted SNAR reactions of fluoro- And chloroarenes as a route to N-aryl indoles and carbazoles

KOH/DMSO-promoted C-N bond formation via nucleophilic aromatic substitution (SNAr) between chloroarenes or fluoroarenes with indoles and carbazole under transition metal-free conditions affording the corresponding N-arylated indoles and carbazoles has been developed.

Unique CuI-pyridine based ligands catalytic systems for N-arylation of indoles and other heterocycles

Two pyridine-based ligands (N-((pyridin-2-yl) methyl) pyridin-2-amine) L1 and (N-((pyridin-2-yl) methylene) pyridin-2-amine) L2 are explored in present work which are inexpensive, effective and environmentally benign in their properties. These have been utilized for C-N cross coupling reaction resulting in N-arylation. The N-arylation of indole, imidazole and triazole have been successfully carried out with different aryl and heteroaryl halides using these ligands.

SBA-15-functionalized melamine-pyridine group-supported palladium(0) as an efficient heterogeneous and recyclable nanocatalyst for N-arylation of indoles through Ullmann-type coupling reactions

SBA-15-functionalized melamine-pyridine group-supported palladium(0) was found to serve as a heterogeneous and recyclable nanocatalyst for N-arylation of indoles with aryl iodides under a low catalyst loading (0.3mol% of Pd) through Ullmann-type C￡N coupling reactions. A variety of aryl iodides could be aminated to provide the N-arylated products in good to excellent yields without the need of an inert atmosphere. Also, this catalyst was found to be an efficient system for the N-arylation of other nitrogen-containing heterocycles with aryl iodides. The heterogeneous palladium catalyst could be recovered by simple filtration of the reaction solution and reused for six cycles without significant loss in its activity.

Palladium nanoparticles supported on modified single-walled carbon nanotubes: A heterogeneous and reusable catalyst in the Ullmann-type N-arylation of imidazoles and indoles

Air- and moisture-stable and recyclable palladium nanoparticles supported on modified single-walled carbon nanotubes (SWCNT-Met/Pd) behave as very efficient heterogeneous catalysts in the Ullmann coupling of imidazoles and indoles with aryl iodides to afford the corresponding C-N coupling reactions under aerobic conditions. These cross coupled products were produced in excellent yields at low palladium loading (～0.2 mol%) and the heterogeneous catalyst can be readily recovered by simple filtration and reused five times without a noticeable loss in its catalytic activity.

Aqueous copper-catalyzed N-arylation of indoles: The surfactant strategy

Surfactants have long been underestimated in synthetic organic chemistry despite their great potential in promoting solubility, reactivity and selectivity in metal-mediated cross-couplings. In this study the strategy of surfactant promotion was exemplified in copper-catalyzed N-arylation of indoles in water. The different effects of surfactants during the coupling reaction were first explored. The superior promoting effect of the natural zwitterionic surfactant, betaine, was found and attributed to the capability of the formed complex to stabilize the copper intermediate in the catalytic transformation and facilitate transportation of the reactants. The concept of surfactant promotion through complexation is valuable in metal-mediated cross-couplings. This method also exhibited good recycling ability. This study will greatly facilitate exploration of surfactant promotion in metal-mediated cross-couplings.

One-Pot N-Arylation of indoles directly from N-arylsulfonylindoles via consecutive deprotection and SnAr reactions with activated aryl halides

An efficient one-pot step by step t-BuOK-mediated procedure for the synthesis of N-arylindoles has been developed in moderate to good yields. The protocol involves the consecutive deprotection of N-arylsulfonylindoles as latent indoles and subsequent SnAr

Synthesis and HIV-1 integrase inhibition activity of some N-arylindoles

Eight simple N-arylindoles were designed, synthesized and evaluated as human immunodeficiency virus (HIV)-1 integrase inhibitors in vitro for the first time. Among these compounds, 3b, 3e and 3g demonstrated significant anti-HIV-1 integrase activity. Especially 3b showed the highest anti-HIV-1 integrase activity with EC50 value of 7.88 μg/ml and TI value of 24.61. Meantime, some structure-activity relationships were also observed and will provide a new lead for design and discovery of more potent N-arylindoles as HIV-1 integrase inhibitors.

Ultrasound-assisted N-arylation of indoles without any catalyst

An efficient method for the ultrasound-assisted N-arylation of indoles with haloarenes in an air atmosphere mediated by Cs2CO3 without any catalyst is reported. N-arylindoles are obtained in moderate to good yields while indoles cross-coupling with activated aryl halides (X = F or Cl). The Japan Institute of Heterocyclic Chemistry.

Microwave-assisted N-arylation of indoles via C(sp2)-N(sp 2) bond formation by aromatic nucleophilic substitution reactions

Microwave-assisted nucleophilic aromatic substitution on aryl halides with different indoles is described. Moderate to good yields are obtained in short reaction time (25-40 min) when coupling indoles with fluoro- and chloro-substituted aryl halides under catalyst-free conditions.

Method for arylating aza-heterocycles with activated aromatic compounds in the presence of caesium carbonate

The invention concerns a process for the preparation of N-aryl-aza-heterocycles of the general formula I by reaction of aza-heterocycles with activated aryl halides with use of caesium carbonate without addition of further catalysts at room temperature.