20538-11-8

Upstream product

• 122-39-4 diphenylamine 
• 70-11-1 α-bromoacetophenone 
• 120-72-9 indole 
• 83566-43-2 tetraphenyl-bismuth trifluoroacetate 
• 23210-25-5 1,3-dihydro-1,3-diphenyl-2H-indol-2-one 
• 536-74-3 phenylacetylene 
• 530-50-7 1,1-Diphenylhydrazine 
• 621-82-9 Cinnamic acid 
• 100-52-7 benzaldehyde 
• 5153-67-3 nitrostyrene 
• 591-50-4 iodobenzene 
• 62-53-3 aniline 
• 108-94-1 cyclohexanone 
• 16096-33-6 1-phenyl-1H-indole 

Downstream Products

• 1423744-01-7 6-methyl-7-phenyl-7H-benzo[c]carbazole 
• 34531-15-2 9-methyl-9-phenyl-9,10-dihydroacridine 

Relevant academic research and scientific papers

TiCl4/t-BuNH2 as the sole catalyst for a hydroamination-based Fischer indole synthesis

A system comprising TiCl4 and t-BuNH2 converts alkynes and hydrazines directly to the corresponding indoles in a highly regioselective manner and generates substituted pyrroles from a 1,3-diyne and aniline derivatives. A system comprising TiCl4 and t-BuNH2 acts as a catalyst for highly regioselective hydroamination reactions of alkynes using hydrazines and at the same time a Lewis acid in the transformation of the generated hydrazones into indole derivatives, while a 1,3-diyne is converted to pyrroles using the same precatalyst.

Pd/β-cyclodextrin-catalyzed C-H functionalization in water: A greener approach to regioselective arylation of (NH)-indoles with aryl bromides

A greener and more practical strategy for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides was developed, in which β-cyclodextrin, acting as both a ligand for Na2PdCl4 and a host for indoles, enables the reactions to occur easily in water. The key advantage of this method is the ingenious merging of aqueous homogeneous catalysis and ligand mediation, leading to the highly regioselective formation of C3-arylindoles with a broad substrate scope and functional-group tolerance. Moreover, the regioselectivity can be switched from the C3 to the C2-position by varying the nature of the base without recourse to employing ArI as substrates.

Three-Component Ordered Annulation of Amines, Ketones, and Nitrovinylarenes: Access to Fused Pyrroles and Substituted Indoles under Metal-Free Conditions

An efficient synthesis of pyrroles and indoles has been developed via three-component ordered annulation of amines, ketones, and nitrovinylarenes. The reaction selectivity can be well controlled under metal-free conditions to afford the corresponding heterocyclic products in good yields.

Catalytic Au(i)/Au(iii) arylation with the hemilabile MeDalphos ligand: Unusual selectivity for electron-rich iodoarenes and efficient application to indoles

The ability of the hemilabile (P,N) MeDalphos ligand to trigger oxidative addition of iodoarenes to gold has been thoroughly studied. Competition experiments and Hammett correlations substantiate a clear preference of gold for electron-enriched substrates both in stoichiometric oxidative addition reactions and in catalytic C-C cross-coupling with 1,3,5-trimethoxybenzene. This feature markedly contrasts with the higher reactivity of electron-deprived substrates typically encountered with palladium. Based on DFT calculations and detailed analysis of the key transition states (using NBO, CDA and ETS-NOCV methods in particular), the different behavior of the two metals is proposed to result from inverse electron flow between the substrate and metal. Indeed, oxidative addition of iodobenzene is associated with a charge transfer from the substrate to the metal at the transition state for gold, but opposite for palladium. The higher electrophilicity of the gold center favors electron-rich substrates while important back-donation from palladium favors electron-poor substrates. Facile oxidative addition of iodoarenes combined with the propensity of gold(iii) complexes to readily react with electron-rich (hetero)arenes prompted us to apply the (MeDalphos)AuCl complex in the catalytic arylation of indoles, a challenging but very important transformation. The gold complex proved to be very efficient, general and robust. It displays complete regioselectivity for C3 arylation, it tolerates a variety of functional groups at both the iodoarene and indole partners (NO2, CO2Me, Br, OTf, Bpin, OMe?) and it proceeds under mild conditions (75 °C, 2 h).

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.

Electronic effect of substituents on anilines favors 1,4-addition to: Trans -β-nitrostyrenes: Access to N -substituted 3-arylindoles and 3-arylindoles

A simple and an efficient method for the regioselective synthesis of N-alkyl/aryl/H 3-arylindole derivatives from N-substituted anilines and trans-β-nitrostyrenes has been described using 10 mol% of bismuth(iii) triflate as a catalyst in acetonitrile at 80 °C. The present protocol profits from the formation of new C-C and C-N bonds, broad substrate scope and moderate to good yields.

Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles

A copper-mediated intramolecular aza-Wacker-type cyclization was developed for the direct and efficient synthesis of 3-aryl indoles using 2-alkenylanilines in moderate to good yields with good functional group compatibility. This strategy shows the high efficiency, operational simplicity as well as broad substrate scope.

Method for synthesizing diphenyl substituted indole compound

The invention relates to a method for synthesizing a diphenyl substituted indole compound which is represented as the following formula (III) and capable of being used as a medical intermediate. The method comprises the steps that the compounds in the following formula (I) and the following formula (II) are reacted in an organic solvent in the presence of bi-component catalysts, phosphine ligand and acid compounds so as to obtain the compound in the formula (III), wherein R1-R2 are H, C1-C6 alk yl or C1-C6 alkoxy, X is halogen and M is an alkali metal element. According to the method, appropriate substrates are selected, a unique catalyst, ligand, acid compound and organic solvent combined reaction system is used, and accordingly target products can be obtained in high yield, and the method has good application prospects and industrial production potentials in the technical field of medical intermediate synthesis.

Divergent reactivity in palladium-catalyzed annulation with diarylamines and α,β-unsaturated acids: Direct access to substituted 2-quinolinones and indoles

A palladium-catalyzed C-H activation strategy has been successfully employed for exclusive synthesis of a variety of 3-substituted indoles. A [3+3] annulation for synthesizing substituted 2-quinolinones was recently developed by reaction of α,β-unsaturate

Atom-economical transformation of diaryliodonium salts: Tandem C-H and N-H arylation of indoles

Arylation using diaryliodonium salts generates one equivalent of an iodoarene as a side-product, a significant waste of atom economy. Here, we show that diaryliodoniums can undergo Cu-catalyzed tandem C-H/N-H arylation, producing novel indoles that incorporate both aryl groups from the reagent.