2415-33-0

Upstream product

• 109-06-8 α-picoline 
• 2196-95-4 2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide 
• 108-89-4 picoline 
• 1122-58-3 dmap 
• 108-99-6 3-Methylpyridine 
• 3558-24-5 1-methyl-2-phenyl-1H-indole 
• 1859-39-8 2-phenyl-N-hydroxyindole 
• 98-88-4 benzoyl chloride 
• 104-94-9 4-methoxy-aniline 
• 68-12-2 N,N-dimethyl-formamide 
• 632-22-4 tetramethylurea 
• 127-19-5 N,N-dimethyl acetamide 
• 948-65-2 2-phenyl-indole 
• 96-96-8 4-methoxy-2-nitroaniline 

Downstream Products

• 81235-58-7 3-(1-methyl-2-phenylindol-3-yl)-2-phenylindole 

Relevant academic research and scientific papers

Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes. An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles

The palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes affords free N-H 2-substituted 3-alkynylindoles in satisfactory to high yield. 2-Substituted 3-alkynylindoles revealed useful intermediates for the regioselective synthesis of 2-substituted 3-acylindoles. The latter can be prepared from o-alkynyltrifluoroacetanilides and 1-bromoalkynes via a one-pot cyclization-hydration protocol, omitting the isolation of 2-substituted 3-alkynylindoles.

Ferrocenyl induced one-pot synthesis of 3,3′-ferrocenylbiindoles

When we used 2-ferrocenethynylaniline (1a) as reactant and NaAuCl4·2H2O (5%) as catalyst to prepare 2-ferrocenylindole (2a), we were surprised to find that 3,3′-ferrocenylbiindole (3a) was obtained simultaneously. 3a was characterized by elemental analysis, FT-IR, MS, NMR, and X-ray single crystal diffraction. The reactant substitution reaction, in-situ HNMR, XPS, EPR characterization, and calculations were carried out to interpret why 3a was obtained in one pot. The results showed that the hydroperoxyl radical played a key role in the reaction, which induced synthesis of 3a.

Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi-Walled Carbon Nanotubes in Liquid Phase

HNO3-oxidized carbon nanotubes catalyze oxidative dehydrogenative (ODH) carbon–carbon bond formation between electron-rich (hetero)aryls with O2 as a terminal oxidant. The recyclable carbocatalytic method provides a convenient and an operationally easy synthetic protocol for accessing various benzofused homodimers, biaryls, triphenylenes, and related benzofused heteroaryls that are highly useful frameworks for material chemistry applications. Carbonyls/quinones are the catalytically active site of the carbocatalyst as indicated by model compounds and titration experiments. Further investigations of the reaction mechanism with a combination of experimental and DFT methods support the competing nature of acid-catalyzed and radical cationic ODHs, and indicate that both mechanisms operate with the current material.

Carbocatalysed Oxidative C sp 2 -C sp 2 Homocouplings of Benzo-Fused Heterocycles

Appropriate and fine-tuned treatments of amorphous carbon (AC) involving aqua regia or concentrated HNO3 lead to oxidised carbon materials (oAC) which are able to catalyse 2,2′- and 3,3′-homocouplings of various functionalised indoles with outs

Cycloisomerization of 2-alkynylanilines to indoles catalyzed by carbon-supported gold nanoparticles and subsequent homocoupling to 3,3′-biindoles

Elevated by the support: 2-Alkynyl aniline cycloisomerization to indole is catalyzed by cationic Au NPs on a carbon support. Electroneutral and rich 2-aryl indoles are further converted into 3,3′-biindoles by oxidative homocoupling that is readily catalyzed by the Au NPs on carbon, and exclusively but also somewhat sluggishly by the carbon support. Copyright

2-Substituted 3-arylindoles through palladium-catalyzed arylative cyclization of 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions

Free NH 2-substituted 3-arylindoles have been prepared usually in good to high yields through the palladium-catalyzed reaction of readily available 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions. The reaction tolerates a variety of useful functional groups both in the arylboronic acid and in the alkyne, including chloro, formyl, and ester groups.

Iron-catalyzed oxidative homo-coupling of indoles via C-H cleavage

A new method for the homo-coupling of indoles has been developed by the use of FeCl3 as catalyst and molecular oxygen as the only oxidant. The protocol provides a practical and straightforward approach toward 3, 3'-biindolyls.

3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones

α-Iodoenones can be efficiently employed as organic electrophiles in the Pd-catalyzed synthesis of 2,3-disubstituted indoles from 2-alkynyltrifluoroacetanilides. Best results were obtained using the weak ligand As(Ph)3. The methodology reported provides an efficient entry to indoles bearing a 2-alkenon-2-yl moiety linked in the 3-position, that possesses a scarcely reported substitution pattern.

2-Substituted 3-aryl- and 3-heteroarylindoles by the palladium-catalyzed reaction of o-trifluoroacetanilides with aryl bromides and triflates

The palladium-catalyzed reaction of aryl and heteroaryl bromides and triflates with o-alkynyltrifluoroacetanilides affords 2-substituted 3-aryl- and heteroarylindoles usually in excellent yield. The procedure can be applied to the synthesis of 2-substituted indole-3-carboxaldehydes.

Radical cations: Reactions of 2-phenylindole with aromatic amines under anodic oxidation. β-Scission of an amino alkoxy radical

2-Phenyl-1H-indole reacts with p-anisidine, 2-nitro-p-anisidine and 2-nitro-p-methylaniline, under anodic oxidation, to give several products, depending on the potential used and on the presence or the absence of oxygen and a deprotonating agent. This investigation gives new insights into the reactivity of radical cations generated by a controlled anodic potential and neutral radicals corresponding to either 2-phenyl-1H-indole or to the three amines studied. The chosen amines show oxidation potentials lower (p-anisidine), equal (2-nitro-p-anisidine) or higher (2-nitro-p-methylaniline) than that of 2-phenyl-1H-indole and the reactions were carried out at the potential of the studied compounds. The oxidation of 2-phenyl-1H-indole in oxygen affords a new indole derivative, whose formation has been explained by β-scission of an indol-2-yloxyl radical and its structure was confirmed by X-ray analysis.