78825-91-9

Upstream product

• 66152-10-1 (2R,3S)-2-Ethyl-2-phenyl-2,3-dihydro-1H-indol-3-ol 
• 66152-10-1 (2R,3R)-2-Ethyl-2-phenyl-2,3-dihydro-1H-indol-3-ol 
• 1007-32-5 benzyl ethyl ketone 
• 100-63-0 phenylhydrazine 
• 622-76-4 1-phenyl-1-butyne 
• 615-43-0 2-iodophenylamine 
• 98-95-3 nitrobenzene 
• 549500-24-5 N-(2-benzoylphenyl)propionamide 
• 61668-44-8 1-phenyl-2-nitrobutane 
• 1217438-26-0 1,1-diphenylbutan-2-one O-acetyl oxime 
• 615-36-1 2-bromoaniline 
• 98-80-6 phenylboronic acid 
• 1885-29-6 anthranilic acid nitrile 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate

Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.

N, N-Dimethylformamide-stabilized palladium nanoclusters as a catalyst for Larock indole synthesis

We show that N,N-dimethylformamide-stabilized Pd nanoclusters (NCs) have high catalytic activity in the reaction of substituted 2-iodoanilines with alkynes to give 2,3-disubstituted indoles. This indole synthesis does not require phosphine ligands and proceeds with low Pd catalyst loadings. The Pd NCs were separated from the mixture after the reaction, and recycled at least three times. Transmission electron microscopy images showed that the Pd particle size before the reaction was 1.5-2.5 nm. The particle size after the reaction was 2-3 nm. X-ray photoelectron spectroscopy showed that the binding energy of the Pd NCs before the reaction was 335.0 eV.

Palladium-catalyzed amination of aromatic C-H bonds with oxime esters

"Chemical equation presented" We report a conceptually new approach to the direct amination of aromatic C-H bonds. In this process, an oxime ester function reacts with an aromatic C-H bond under redox-neutral conditions to form, in the case studied, an indole product. These reactions occur with relatively low catalyst loading (1 mol %) by a mechanism that appears to involve an unusual initial oxidative addition of an N-O bond to a Pd(0) species. The Pd(II) complex from oxidative addition of the N-X bond has been isolated for the first time, and evidence for the intermediacy of such oxidative addition products in the catalytic reaction has been gained.

Annulation of internal alkynes through a hydroamination/aza-Heck reaction sequence for the regioselective synthesis of indoles

Highly regioselective annulation reactions of unsymmetrically substituted alkynes by primary 2-bromo or 2-chloroanilines are achieved with an efficient one-pot protocol, which relies on a regioselective TiCl4-catalyzed intermolecular hydroamination and a subsequent palladium-catalyzed intramolecular aza-Heck reaction. The use of unsymmetrically substituted alkynes in this strategy enables the synthesis of diversely functionalized indoles, with a regioselectivity that is complementary to the one obtained when employing Larock's annulation reaction.

One-pot synthesis of polysubstituted indoles from aliphatic nitro compounds under mild conditions

Polysubstituted indoles can be prepared directly from functionalized nitroalkanes under very mildly acidic conditions in a simple, one-pot, two-stage procedure.

Facile preparation of 2,3-disubstituted indole derivatives through low-valent titanium induced intramolecular reductive coupling reactions of acylamido-carbonyl compounds

An efficient synthesis of 2,3-disubstituted indole derivatives through low-valent titanium induced reductive cyclisation of suitably substituted acylamido-carbonyl compounds is described.

SmI2 mediated synthesis of 2,3-disubstituted indole derivatives

A novel preparation of 2,3-disubstituted indole derivatives was achieved through SmI2 induced intramolecular reductive coupling reactions of acylamido carbonyl compounds.

A novel and direct synthesis of indoles via catalytic reductive annulation of nitroaromatics with alkynes

Indoles are produced regioselectively and in moderate yields from the reactions of nitroaromatics with alkynes catalyzed by [CpM(CO)2]2 (1; [(η5-C5H5)Fe(CO)2] 2; [(η5-C5Me5)-Fe(CO)2] 2; [(η5-C5Me5)Ru(CO)2] 2) under carbon monoxide.

Traceless solid phase synthesis of 2,3-disubstituted indoles

An efficient method for the traceless solid phase synthesis of 2,3- disubstituted indoles using a THP linker and a Pd(0)-mediated annulation of 2-iodoaniline and acetylenes is reported.

Zeolites as Catalysts in the Fischer Indole Synthesis. Enhanced Regioselectivity for Unsymmetrical Ketone Substrates

The use of zeolites as catalysts in the Fischer indole synthesis has been studied on five unsymmetrical ketone substrates with 14 different zeolites.Both the corresponding phenylhydrazone and the parent ketone in the presence of phenylhydrazine were used as substrates.Zeolites which catalysed the indolization of the phenylhydrazones were also active in the direct conversion of the parent ketone.For substrates which gave mixtures of isomeric indoles under homogeneous, classical indolization conditions in acetic acid, it was found that the distribution of regioisomersof the indoles formed was altered considerably by zeolite catalysis and that the distribution was dependent on the type of zeolite used.A one-pot synthetic procedure for indole synthesis from the parent ketone and phenylhydrazine is described.