128200-46-4

Usage

Class

Indole class of organic compounds

Structure

Five-membered ring with a nitrogen atom

Common use

Building block in the synthesis of pharmaceutical and agrochemical products

Chemical reactivity

Diverse

Biological activities

Anti-inflammatory and anticancer properties

Role in development

New materials

Use in reactions

Organic synthesis reactions

Upstream product

• 27816-53-1 1,5-dimethyl-1H-indole 
• 67-68-5 dimethyl sulfoxide 
• 68-12-2 N,N-dimethyl-formamide 
• 140-29-4 phenylacetonitrile 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 75-05-8 acetonitrile 

Relevant academic research and scientific papers

Cu-Catalyzed Cyanation of Indoles with Acetonitrile as a Cyano Source

Cu-catalyzed cyanation of indoles with acetonitrile for the synthesis of 3-cyanoindoles has been developed. The Cu/TEMPO/(Me3Si)2 system has been identified to promote highly efficient and selective C-H cyanation of indoles by use of unactivated acetonitrile as a cyano source via a sequential iodination/cyanation process in one pot. This reaction furnishes 3-cyanoindoles in moderate to good yields and tolerates a series of functional groups. Moreover, low-cost copper catalysts and hazardless acetonitrile as a cyano source feature the practicability of this reaction.

Direct C-2 Carboxylation of 3-Substituted Indoles Using a Combined Br?nsted Base Consisting of LiO-tBu/CsF/18-crown-6

Herein, we report that a combination of LiO-tBu, CsF, and 18-crown-6 can be used to carry out the carboxylation of indole derivatives at the C-2 position under an ambient CO2 atmosphere. Substrates bearing an electrophilic substituent (i.e., cyano, formyl, benzoyl, phenylsulfonyl, phenylsulfinyl, and chloride) at the C-3 position are smoothly converted into their corresponding carboxylated products with high functional group compatibility.

An insight on the influence of surface Lewis acid sites for regioselective C–H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst

The Cu dispersed on mesoporous SBA-15 has demonstrated the regioselective C–H bond C3-cyanation of indoles by in-situ generation of –CN using DMF and NH4I in presence of O2. Pyridine adsorbed diffuse reflectance infrared spectroscopy (DRIFTS) results revealed that surface Cu2+ species are acting as Lewis acid sites in the in-situ generation of cyano- group for the synthesis of indole nitriles. A direct correlation between Cu metal surface area and the indole nitrile yields are established and the dual role of copper is substantiated by N2O titration and XPS techniques. The 10 wt%Cu/SBA-15 demonstrated superior performance when compared to Pd, Ru supported on SBA-15. The 10 wt%Cu/SBA-15 catalyst showed consistent activity and selectivity after the 4th cycle.

Copper-mediated selective aerobic oxidative C3-cyanation of indoles with DMF

Under an oxygen atmosphere, the copper-mediated direct C3-cyanation of indole C-H bonds, using cheap and safe DMF as a CN source, took place selectively to produce the corresponding C3-cyanoindoles in good yields. A possible mechanism for this selective cyanation was proposed.

Copper-mediated C3-cyanation of indoles by the combination of amine and ammonium

A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N′,N′-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H2O followed by hydrolyzation to form the aldehyde. Then the reaction between the aldehyde and ammonium afforded nitriles. The reaction employs O2 as a clean oxidant with good efficiency and functional group tolerance. Thus, it represents a facile and safe procedure leading to 3-cyano indoles. The Royal Society of Chemistry 2014.

Cyanation of indoles with benzyl cyanide as the cyanide anion surrogate

A copper-mediated direct cyanation of indoles with benzyl cyanide as the cyanide anion surrogate has been achieved. The cascade reaction furnished 3-cyanoindoles under mild reaction conditions in good to excellent yields with various functional groups tolerance.

Copper-mediated selective cyanation of indoles and 2-phenylpyridines with ammonium iodide and DMF

Copper-mediated regioselective cyanation of indoles and 2-phenylpyridines was developed by using ammonium iodide and DMF as the combined source of a cyano unit under Pd-free conditions. Mechanistic studies indicate that the reaction of indoles proceeds through a two-step sequence: electrophilic initial iodination and then cyanation. The cyanation has a broad substrate scope, high functional group tolerance, and excellent regioselectivity.

Iron-mediated cyanation of methoxybenzene, indole, and 2-arylpyridine C-H bonds

An iron-mediated direct cyanation of indole and 2-arylpyridine C-H bonds is described. Notably, trimethoxybenzene reacted smoothly under the procedure, forming a C-CN bond via C-H bond cleavage without chelation assistance. Georg Thieme Verlag Stuttgart · New York.

The palladium-catalyzed cyanation of indole C-H bonds with the combination of NH4HCO3 and DMSO as a safe cyanide source

A palladium-catalyzed cyanation of the 3-position of indole sp2 C-H bonds by the combination of NH4HCO3 and DMSO as the "CN" source was achieved to provide aromatic nitriles in moderate to good yields with excellent regioselectivity. It represents a practical and safe cyanation method.

Palladium-catalyzed direct cyanation of indoles with K4[Fe(CN) 6]

"Chemical equation presented" Direct cyanation of Indole derivatives has been achieved with nontoxic K4[Fe(CN)6] as cyanating agent through Pd-catalyzed C-H bond activation.