52604-15-6

Upstream product

• 5350-41-4 trimethylbenzylammonium bromide 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 
• 3377-71-7 N-benzylindole 
• 10271-57-5 1-chloro-2-(2-phenylethynyl)benzene 
• 100-46-9 benzylamine 
• 615-41-8 2-iodochlorobenzene 
• 98-81-7 1-bromovinylbenzene 
• 583-53-9 2,3-dibromobenzene 
• 59904-14-2 (Z)-N-(1-Methyl-2-phenylethyliden)benzolamin 
• 98-80-6 phenylboronic acid 
• 201230-82-2 carbon monoxide 

Downstream Products

• 948-65-2 2-phenyl-indole 
• 1322697-70-0 1-benzyl-2-phenyl-1H-indole-3-carbonitrile 
• 702702-82-7 1-benzyl-2-phenyl-1H-indol-3-ol 
• 142677-04-1 1-benzyl-2-phenyl-1H-indole-3-carbaldehyde 
• 77435-12-2 ethyl 1-benzyl-2-phenyl-1H-indole-3-carboxylate 
• 1613218-93-1 C₂₇H₂₁NS 
• 1594796-52-7 1-benzyl-3-bromo-2-phenyl-1H-indole 
• 1594796-69-6 1-benzyl-3-iodo-2-phenyl-1H-indole 
• 1322089-37-1 1-benzyl-3,3-difluoro-2-phenylindolin-2-ol 
• 1198116-11-8 11-benzyl-5,6-diphenyl-11H-benzo[a]carbazole 

Relevant academic research and scientific papers

An Efficient Route to Highly Substituted Indoles via Tetrahydroindol-4(5H)-one Intermediates Produced by Ring-Opening Cyclization of Spirocyclopropanes with Amines

An efficient route to highly substituted indoles was developed. It included regioselective functionalization of tetrahydroindol-4(5H)-ones, prepared by ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes with primary amines, and subsequent oxidation. The 6-substituted indoles were synthesized from a readily available 5-substituted cyclohexane-1,3-dione-2-spirocyclopropane. The synthesis of 5- and 7-substituted indoles was achieved by regioselective electrophilic alkylation of tetrahydroindol-4(5H)-one, followed by oxidation. The 4-substituted indoles were synthesized by nucleophilic alkylation of the corresponding pyrrole derivative, which was prepared by partial oxidation of tetrahydroindol-4(5H)-one, and sequential oxidation. The synthesis of 4-substituted indoles was also accomplished by palladium-catalyzed coupling of 4-hydroxyindole-derived triflates. Furthermore, the synthesis of 4,5,6,7-tetrasubstituted indoles was achieved by using these regioselective alkylations.

Iron-Catalyzed Reductive Cyclization by Hydromagnesiation: A Modular Strategy Towards N-Heterocycles

A reductive cyclization to prepare a variety of N-heterocycles, through the use of ortho-vinylanilides, is reported. The reaction is catalyzed by an inexpensive and bench-stable iron complex and generally occurs at ambient temperature. The transformation likely proceeds through hydromagnesiation of the vinyl group, and trapping of the in situ generated benzylic anion by an intramolecular electrophile to form the heterocycle. This iron-catalyzed strategy was shown to be broadly applicable and was utilized in the synthesis of substituted indoles, oxindoles and tetrahydrobenzoazepinoindolone derivatives. Mechanistic studies indicated that the reversibility of the hydride transfer step depends on the reactivity of the tethered electrophile. The synthetic utility of our approach was further demonstrated by the formal synthesis of a reported bioactive compound and a family of natural products.

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes

A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.

Direct C-H bond activation: Palladium-on-carbon as a reusable heterogeneous catalyst for C-2 arylation of indoles with arylboronic acids

Direct C(sp2)-H bond functionalization of indoles with arylboronic acids is achieved using palladium supported on carbon as a reusable heterogeneous catalyst in the presence of an oxidant under mild conditions. The current protocol formed exclusive C-2 selective products without the aid of any ligand or directing group. The catalyst is reusable for up to four catalytic cycles with the retention of catalytic efficiency.

Mechanochemical Pd(II)-Catalyzed Direct and C-2-Selective Arylation of Indoles

A mechanochemical method for the preparation of synthetically useful 2-arylindoles is developed using Pd(II) as the catalyst in the absence of phosphine ligands in a ball-mill. The developed protocol is highly C-2 selective and tolerant of structural variations with electron-rich and electron-deficient substituents both in indoles and iodoarenes. Arylation is possible in both unprotected indoles and N-protected indoles with the electron-donating group with the former substrate being relatively slower to react and little less yielding. Indoles with a deactivated five-membered ring could also take part in the reaction with ease. The scalability of the reaction was demonstrated by conducting the reaction in the gram scale. In general, the reactions were achieved in a shorter time than the conventional methods.

Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage

In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.

Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates

The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.

Valorization of CO2: Preparation of 2-Oxazolidinones by Metal-Ligand Cooperative Catalysis with SCS Indenediide Pd Complexes

The capture and utilization of CO2 to prepare high-value compounds is very attractive chemically and highly desirable socially. Indenediide-based Pd SCS pincer complexes are shown here to promote the carboxylative cyclization of propargylamines

Borane-catalyzed indole synthesis through intramolecular hydroamination

The reaction of 2-alkynyl anilines with catalytic amounts of B(C6F5)3 (5 mol%) resulted in the formation of 2-substituted indoles according to an intramolecular hydroamination in good to excellent yields. Reaction intermediates as well as products were characterized by NMR spectroscopy and by X-ray crystallography. The domino hydroamination/hydrogenation sequence allowed the efficient synthesis of tetrahydroquinoline 8 in good yield.