61843-42-3

Upstream product

• 6127-49-7 2-(4-bromophenyl)indole 
• 74-88-4 methyl iodide 
• 106-40-1 4-bromo-aniline 
• 120-72-9 indole 
• 100-61-8 N-methylaniline 
• 1122-91-4 4-bromo-benzaldehyde 
• 603-76-9 1-methylindole 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 34176-08-4 sodium 4-bromobenzenesulfinate 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 88848-28-6 2-(4-Bromo-phenyl)-3-[(Z)-3-[2-(4-bromo-phenyl)-1-methyl-1H-indol-3-yl]-2-methyl-prop-2-en-(E)-ylidene]-1-methyl-3H-indolium; chloride 
• 79573-69-6 2-(4-Bromo-phenyl)-3-[(E)-3-[2-(4-bromo-phenyl)-1-methyl-1H-indol-3-yl]-prop-2-en-(E)-ylidene]-1-methyl-3H-indolium; chloride 
• 79573-70-9 3-[(Z)-2-Bromo-3-[2-(4-bromo-phenyl)-1-methyl-1H-indol-3-yl]-prop-2-en-(E)-ylidene]-2-(4-bromo-phenyl)-1-methyl-3H-indolium; chloride 
• 1334159-64-6 2-(4-bromophenyl)-1-methyl-1H-indole-3-carbonitrile 

Relevant academic research and scientific papers

In Situ Preparation of Palladium Nanoparticles for C-2 Selective Arylation of Indoles in Agro-Waste Extract Based Mixed Solvents

An efficient and practical method for the in situ generation of palladium nanoparticles was successfully established in a water extract of pomelo peel ash. The produced palladium nanoparticles were characterized by energy-dispersive X-ray spectroscopy elemental mapping, field emission scanning electron microscopy, high-resolution transmission electron microscope, X-ray powder diffraction, and showed high catalytic activity for selective C-2 arylation of indoles. A series of 2-arylindoles were smoothly installed in moderate to good yields through the direct palladium-catalyzed cross-coupling reactions of indoles and iodoarenes without external ligand, base, oxidant, and preinstallation directing group.

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.

NaNO2/K2S2O8-mediated Selective Radical Nitration/Nitrosation of Indoles: Efficient Approach to 3-Nitro- and 3-Nitrosoindoles

JPZ acknowledges financial support from the National Natural Science Foundation of China (No. 21172163, 21472133), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1749). (Figure presented.).

Preparation method of indole compounds

The invention provides a preparation method of indole compounds. 2-cyanoethylene oxide compounds and arylamine react under the catalysis effect of lewis acid (boron trifluoride diethyl etherate or aluminum trichloride) to obtain corresponding indole compo

Oxygenophilic Lewis Acid Promoted Synthesis of 2-Arylindoles from Anilines and Cyanoepoxides in Alcohol

A convenient synthetic method to indoles from anilines and cyanoepoxides was developed under the catalysis of BF3·OEt2 or AlCl3 in alcohols. The reaction involves a tandem reaction of the regiospecific ring-opening of cyanoepoxides with anilines, elimination of cyanide, intramolecular aromatic electrophilic substitution, and water elimination. The Lewis acid generated protic acid is an efficient catalyst. The method features readily accessible starting materials, wide substrate scope, transition-metal-free environment, and regiospecificity in the ring-opening of cyanoepoxides.

Eco-friendly solvents for palladium-catalyzed desulfitative C-H bond arylation of heteroarenes

Herein, we report the Pd-catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross-coupling that can be performed in diethyl carbonate (DEC) or cyclopentyl methyl ether (CPME) as green and renewable solvents or even in neat conditions instead of dioxane or dimethylacetamide (DMA). Under these solvent conditions, the reaction proceeds with a wide range of heteroarenes. C2- or C5-arylated products were obtained with furan and pyrrole derivatives. Benzofuran was also arylated regioselectively at the C2-position, whereas the reaction proceeds selectively at the C3- or C4-positions if thiophenes and benzothiophenes are used. Moreover, in some cases, especially with 1-methylindole, solvent-free conditions afforded better regioselectivities and/or yields than the reaction performed in the presence of solvents.

Palladium-catalysed direct desulfitative arylation of pyrroles using benzenesulfonyl chlorides as alternative coupling partners

The reactivity of pyrrole derivatives for palladium-catalysed desulfitative arylation has been investigated. 1-Methyl-, 1-phenyl- and 1-benzylpyrroles were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine-free catalyst. Highly regioselective arylations at carbon C2 of pyrroles were observed in all cases. A wide variety of substituents on the benzenesulfonyl derivative was tolerated. It should be noted that even bromo- and iodo-benzenesulfonyl chlorides were successfully coupled with pyrrole derivatives without cleavage of the C-Br or C-I bonds, allowing further transformations. Surprisingly, with indoles, mixtures of C2- and C3-arylation products were obtained.

On water phosphine-free palladium-catalyzed room temperature C-H arylation of indoles

Get on top of your chemistry! An "on water", palladium-catalyzed, phosphine-free direct C-H arylation of indoles, with iodoarenes at 25-30°C, is disclosed (see scheme; TBDMS=N-tert-butyldimethylsilyl ether; SEM=N-2-(trimethylsilyl)ethoxymethyl; Bn=benzyl, Piv=pivabyl). The mildness of the reaction conditions permits the tolerance of a variety of N1-protected indoles.

Palladium-catalyzed direct and site-selective desulfitative arylation of indoles with sodium sulfinates

An efficient method was developed for the desulfitative arylation of indoles with sodium sulfinates using palladium as catalyst and copper chloride dihydrate as oxidant. The direct arylation occurred exclusively in the C-2 position of indoles and proceeded well for a range of different substrates. Copyright

Fluorous silica gel-supported perfluoro-tagged palladium nanoparticles: An efficient and reusable catalyst for direct C-2 arylation of indoles

The preparation of FSG-supported palladium nanoparticles and their application in direct C-2 arylation of indoles are presented. Moderate to good yields were obtained with ultra-low catalyst loading. The catalyst could be easily recovered by simple workup and reused up to seven runs with only a slight decrease in its activity. The Royal Society of Chemistry 2011.