154796-08-4

Upstream product

• 64-17-5 ethanol 
• 79409-00-0 2-(methyl(phenyl)amino)-1-(p-tolyl)ethan-1-one 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 6832-87-7 2-bromo-N-methylaniline 
• 60655-80-3 (E)-4-methylstyrenyl bromide 
• 619-41-0 4-(bromoacetyl)toluene 
• 100-61-8 N-methylaniline 
• 603-76-9 1-methylindole 
• 1038997-78-2 (4-methylphenyl)(2,4,6-triisopropylphenyl)iodonium triflate 
• 106-38-7 para-bromotoluene 
• 30015-86-2 3-(4-methylphenyl)-1H-indole 
• 74-88-4 methyl iodide 
• 104-09-6 4-methylphenylacetaldehyde 
• 699-02-5 4-Methylphenethyl alcohol 

Downstream Products

• 51358-08-8 1-methyl-2-(4-methylphenyl)indole 

Relevant academic research and scientific papers

Ring-expanded N-heterocyclic carbenes as ligands in iron-catalysed cross-coupling reactions of arylmagnesium reagents and aryl chlorides

The structure-activity relationship of expanded-ring N-heterocyclic carbenes (NHCs) in the iron-catalysed Kumada aryl-aryl coupling reaction was explored. This was achieved by comparing the catalytic performance of Fe-NHC catalysts generated in situ containing NHCs that differ in steric bulk. In particular, the influences of ring sizes (5-8) and N-aryl substituents were explored in terms of spectroscopic and structural features, which affect their %Vbur values. The three best performing ligands were found on a diagonal of a 5 × 4 structural matrix revealing an optimal steric bulk and significant influences of subtle steric variations on the catalytic activities.

C3-Arylation of indoles with aryl ketonesviaC-C/C-H activations

C3-Arylation of indoles with aryl ketones is accomplishedviapalladium-catalyzed ligand-promoted Ar-C(O) cleavage and subsequent C-H arylation of indole. Various (hetero)aryl ketones are compatible in this reaction, affording the corresponding 3-arylindoles in moderate to good yields. Further introduction of an indole moiety into the natural products desoxyestrone and evodiamine demonstrate the synthetic utility of this protocol.

Ascorbic Acid as an Aryl Radical Inducer in the Gold-Mediated Arylation of Indoles with Aryldiazonium Chlorides

In recent years interest in the development of protocols that facilitate the oxidative addition of gold to access mild cross-coupling processes mediated by this metal has increased. In this context, we report herein that ascorbic acid, a natural and readily accessible antioxidant, can be used to accelerate the oxidative addition of aryldiazonium chlorides onto AuI. The aryl–AuIII species generated in this way, has been used to prepare 3-arylindoles in a one-pot protocol starting from anilines and para-, meta-, and ortho- substituted aryldiazonium chlorides. The mechanism underlying the oxidative addition has been examined in detail based on EPR analyses, cyclic voltammetry, and DFT calculations. Interestingly, we have found that in this protocol, the chloride atom induces the AuII/AuIII oxidation step.

Abnormal NHC supported palladacycles: Regioselective arylation of heteroarenes via decarboxylation

We report synthesis of two new palladium(II) complexes of abnormal N-heterocyclic carbene ligands. The catalytic activity of these palladium(II) complexes was examined for the decarboxylative arylation of N-methylindole-carboxylic acids. An exclusive regioselectivity and very good yields were obtained with a variety of aryl halide partners.

HFIP-promoted Bischler indole synthesis under microwave irradiation

1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) was found to be effective for the Bischler indole synthesis under microwave irradiation in the absence of a metal catalyst. Under the catalysis of HFIP, a wide range of α-amino arylacetones were successfully transf

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.

Metal-free, C-H arylation of indole and its derivatives with aryl diazonium salts by visible-light photoredox catalysis

In this Letter, we present the Rhodamine B catalyzed direct C-H arylation of indole with aryl diazonium salts. This method only requires green light and room temperature.

Water-medium C-H activation over a hydrophobic perfluoroalkane-decorated metal-organic framework platform

The use of water as reaction medium in the heterogeneous activation of C-H bonds has numerous advantages in terms of environmental benign, safety and cost efficiency impact. However, it is severely hampered because the reactants are difficult to dissolve in water and contact with the active sites of heterogeneous catalysts. Herein, we choose perfluoroalkane-functionalized mesoporous metal-organic framework (MOF) NU-1000 as a hydrophobic platform to encapsulate ultrafine palladium nanoparticles (Pd NPs) for C-H activation in water. The resultant Pd NPs stabilized by the perfluoroalkane exhibited high activity and regioselectivity in the direct C-H arylation of indoles in water. The introduction of perfluoroalkane chains into the mesoporous pores of NU-1000 provides hydrophobic surfaces to facilitate access of the reactants to the active sites to guarantee the high activity.

NH4PF6-promoted cyclodehydration of α-amino carbonyl compounds: Efficient synthesis of pyrrolo[3,2,1-ij]quinoline and indole derivatives

NH4PF6 is an inexpensive, safe, and low-toxicity inorganic salt; it was found to promote the cyclodehydration of α-amino carbonyl compounds in the absence of metal reagents. This simple cyclodehydration strategy enables highly atom-e

Indium-catalyzed annulation of 3-aryl- and 3-heteroarylindoles with propargyl ethers: Synthesis and photoluminescent properties of aryl- and heteroaryl[c]carbazoles

Treatment of 3-aryl- and 3-heteroarylindoles with propargyl ethers under indium catalysis successfully provided aryl- and heteroaryl[c]carbazoles, which were found to be more efficient emitters compared with the corresponding [a]-analogs.