51206-91-8

Upstream product

• 603-76-9 1-methylindole 
• 1038997-85-1 (4-bromophenyl)(2,4,6-triisopropylphenyl)iodonium triflate 
• 120-72-9 indole 
• 106-40-1 4-bromo-aniline 
• 59862-55-4 (E)-1-(4-bromophenyl)ethan-1-one oxime 
• 1104637-53-7 B-ethynyl N-methyliminodiacetic acid boronate 
• 589-87-7 1,4-bromoiodobenzene 
• 501358-04-9 1-(4-bromophenyl)-2-(methyl(phenyl)amino)ethan-1-one 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 172984-02-0 N-(2-iodoanilinomethyl)succinimide 
• 57056-93-6 N-methyl-2-iodoaniline 
• 615-43-0 2-iodophenylamine 
• 172983-98-1 1-(4-Bromo-phenyl)-2-[(2-iodo-phenyl)-methyl-amino]-ethanone 
• 172983-80-1 3-(4-Bromo-phenyl)-1-methyl-2,3-dihydro-1H-indol-3-ol 

Relevant academic research and scientific papers

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.

Au(i)/Au(iii)-Catalyzed C-N coupling

Cycling between Au(i) and Au(iii) is challenging, so gold-catalyzed cross-couplings are rare. The (MeDalphos)AuCl complex, which we showed was prone to undergo oxidative addition, is reported here to efficiently catalyze the C-N coupling of aryl iodides and amines. The transformation does not require an external oxidant or a directing group. It is robust and works with a wide scope of aryl iodides and N-nucleophiles under mild conditions. Mechanistic studies, including the NMR and MS characterization of a key aryl amido Au(iii) complex, strongly support a 2e redox cycle in which oxidative addition precedes transmetalation and reductive elimination is the rate-determining step.

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

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.

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

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.

Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions

We have developed a new site-selective Cu(II)-catalyzed C-H bond functionalization process that can selectively arylate indoles at either the C3 or C2 position under mild conditions. The scope of the arylation process is broad and tolerates broad functionality on both the indole and aryl unit, which makes it amenable to further elaboration. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl species that undergoes initial electrophilic addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group from C3 to C2, and this can be controlled by the nature of the group on the nitrogen atom; free (NH)- and N-alkylindoles deliver the C3-arylated product, whereas N-acetylindoles afford the C2 isomer, both with excellent yield and selectivity. Copyright

A NEW SYNTHESIS OF 3-SUBSTITUTED INDOLINES AND INDOLES

3-Phenyl- and 3-alkyl-3-hydroxyindolines were synthesized by intramolecular Barbier reaction of phenyl and alkyl N-(2-iodophenyl)-N-methylaminomethyl ketones with n-BuLi, which were easily prepared from N-methyl-2-iodoaniline and bromomethyl ketones.The treatment of the indolines with acid gave the corresponding indoles in quantitative yields.