33555-17-8

Upstream product

• 78987-25-4 N-benzoyl-1-amino-2-methylnaphthalene 
• 42350-78-7 (2-oxo-2-phenylethyl)triphenylarsonium bromide 
• 134-32-7 1-amino-naphthalene 
• 107784-21-4 (2-Phenylethynyl-naphthalen-1-yl)-carbamic acid ethyl ester 
• 40113-76-6 N-(1-naphthyl) benzophenone hydrazone 
• 98-86-2 acetophenone 
• 2246-44-8 1-amino-2-methylnaphthalene 
• 886853-74-3 2-(2,2-dibromo-vinyl)-naphthalen-2-ylamine 
• 98-80-6 phenylboronic acid 
• 93-56-1 phenylethane 1,2-diol 
• 96-09-3 styrene oxide 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 28203-05-6 dimethoxy-2,2 phenyl-2 ethanol-1 
• 881-03-8 1-nitro-2-methylnaphthalene 

Downstream Products

• 105492-09-9 6,7-benzo-3-amino-2-phenylindole 
• 105492-30-6 C₁₉H₁₆N₄O 
• 105492-11-3 (2-Phenyl-1H-benzo[g]indol-3-yl)-carbamic acid ethyl ester 
• 153684-35-6 2-phenyl-4H-naphth<1,2-d><1,3>oxazin-4-one 
• 23768-21-0 1-methyl-2-phenyl-1H-benzo[g]indole 

Relevant academic research and scientific papers

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

Method for synthesizing 2-substituted indole compound from iodobenzene and oxime ester under catalysis of palladium

The invention belongs to the technical field of organic chemistry, and discloses a method for synthesizing a 2-substituted indole compound from iodobenzene and oxime ester under the catalysis of palladium. The method comprises the following steps of reacting an oxime ester compound with iodobenzene under the action of a palladium catalyst, a phosphine ligand and norbornene by taking an organic solvent as a reaction medium in a protective atmosphere, and carrying out subsequent treatment to obtain the 2-substituted indole compound. According to the method, palladium is used as a catalyst, the phosphine ligand is adopted, the yield is high, and the substrate applicability is wide. In addition, the oxime ester compound is used as a raw material, and the method has the advantages of cheap and easily-prepared raw materials, simple operation, mild reaction conditions and the like.

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.

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

Synthesis of 2-substituted indole with Hantzsch ester catalyzed by palladium

An efficient reductive cyclization of o-nitrobenzyl ketone compounds was achieved by using a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. 2-Substituted indoles were obtained in good yields. Investigation of the mechanism suggests that palladium hydride promotes the reduction of nitro group, and acetic acid was beneficial for the loss of water to produce the intended product. This reaction system can not only broaden the use of Hantzsch 1,4-dihydropyridine ester, but it also provides a novel approach for preparing indole compounds.

Iron-Catalyzed Reductive Cyclization of o-Nitrostyrenes Using Phenylsilane as the Terminal Reductant

Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene.

Investigation and Application of Amphoteric α-Amino Aldehyde: An in Situ Generated Species Based on Heyns Rearrangement

In situ generation of the reactive amphoteric α-amino aldehyde with simple α-hydroxy ketones and phenylamine via Heyns rearrangement was proven to be feasible. Metal-free domino reactions based on this reactive intermediate were effectively used to afford important N-heterocycles including polysubstituted pyrroles, indoles, and quinoxalines conveniently. A simple starting material, water as the only byproduct, and diversity of the useful products will make this method greatly attractive for pharmaceutics.

Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols

The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byproducts.

Enantioselective arylative dearomatization of indoles via pd-catalyzed intramolecular reductive heck reactions

A highly enantioselective intramolecular arylative dearomatization of indoles via palladium-catalyzed reductive Heck reactions was developed. The new strategy led to a series of optically active indolines bearing C2-quaternary stereocenters in modest to good yields with excellent enantioselectivities (up to 99% ee).

Ruthenium-catalyzed synthesis of indoles from anilines and epoxides

A general synthetic route to indoles from readily available anilines and epoxides by using ruthenium catalysis is described. This straightforward transformation allows a variety of indoles to be obtained in good yields by using [Ru3(CO)12]/1,1-bis(diphenylphosphino)ferrocene as the catalytic system. Water and hydrogen are formed as the only stoichiometric by-products, making this process highly atom efficient.