4677-05-8

Upstream product

• 2684-02-8 benzenediazonium 
• 78395-78-5 1-methyl-2-phenyl-3-hydroxymethylindole 
• 67335-20-0 3,3'-(phenylmethylene)bis(1-methyl-2-phenyl-1H-indole) 
• 3558-24-5 1-methyl-2-phenyl-1H-indole 
• 62-53-3 aniline 
• 36719-71-8 1-phenyl-3,3-tetramethylenetriazene 
• 603-76-9 1-methylindole 
• 369-57-3 benzenediazonium tetrafluoroborate 

Downstream Products

• 78395-71-8 1-methyl-2-phenyl-3-nitro-1H-indole 
• 78395-75-2 3-(4-nitrophenyldiazenyl)-1-methyl-2-phenyl-1H-indole 
• 78395-79-6 1-methyl-3,4-dinitro-2-phenylindole 
• 78602-05-8 1-methyl-2-phenyl-1H-indol-3-yl benzoate 

Relevant academic research and scientific papers

Mild and selective base-free C-H arylation of heteroarenes: experiment and computation

A mild and selective C-H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck-Matsuda type coupling mechanism.

Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions

An efficient, mild, and metal-free approach to direct diazenylation of N-heterocyclic compounds with aryltriazenes using Br?nsted ionic liquid as a promoter has been developed for the first time. Many N-heterocyclic azo compounds were synthesized in good to excellent yields at room temperature under an open atmosphere. Notably, the promoter 1,3-bis(4-sulfobutyl)-1H-imidazol-3-ium hydrogen sulfate could be conveniently recycled and reused with the same efficacies for at least four cycles.

Phenylazoindole dyes 3: Determination of azo-hydrazone tautomers of new phenylazoindole dyes in solution and solid state

A new two series of phenylazo indole dyes was synthesized and the structures of the dyes were confirmed by UV-vis, FT-IR, HRMS and 1H/13C NMR spectroscopic techniques. Five of these dyes (I, I′, II′, III and III′) were also characterized in solid state by using single crystal X-ray diffraction studies besides other spectroscopic techniques. The geometries of the azo and hydrazone tautomeric forms of the dyes were optimized by using Density Functional Theory (DFT). In addition, the effects of the donor and acceptor groups on the azo and hydrazone forms of the dyes were evaluated experimentally and theoretically. The results indicate that the phenylazoindole dyes derived from 2-phenyl indole as coupling component exist as azo form in solution, gas phase and solid state.

Electrophilic ipso-Substitutions. Part 2. Reactions of 3-Substituted Indoles and 4-Substituted NN-Dimethylanilines with Arenediazonium Ions

3-Substituted indoles and 4-substituted NN-dimethylanilines react with arenediazonium ions to form 3-arylazo-indoles and 4-arylazo-NN-dimethylanilines, respectively.The formation of the ?-complex intermediate was interpreted both as electrophilic ipso-attack and as coupling of two radicals deriving from an electron transfer process.Both mechanisms are discussed on the basis of the experimental evidence and on the substrate oxidation potentials.The leaving abilities of the substituents are discussed on the basis of the experimental results.