132554-35-9

Upstream product

• 13228-36-9 5-methyl-2-phenyl-1H-indole 
• 27816-53-1 1,5-dimethyl-1H-indole 
• 98-80-6 phenylboronic acid 
• 74-89-5 methylamine 
• 264912-27-8 1-bromo-2-(phenylethynyl)-4-methylbenzene 
• 614-96-0 5-methyl-1H-indole 
• 536-74-3 phenylacetylene 
• 1207518-08-8 N-methyl-4-methyl-2-(2-phenylethynyl)phenylamine 
• 1448145-42-3 N,5-dimethyl-2-phenyl-3-(phenylselenyl)-1H-indole 
• 2996-92-1 phenyl trimethylsiloxane 
• 132554-28-0 3-(5-Methyl-pyridin-2-yl)-1-phenyl-propan-1-one 
• 591-50-4 iodobenzene 
• 98-86-2 acetophenone 
• 539-44-6 N-4-methylphenylhydrazine 

Downstream Products

• 102316-68-7 (1,5-dimethyl-2-phenyl-indol-3-yl)-glyoxylic acid dimethylamide 
• 112044-26-5 2-dimethylamino-1-(1,5-dimethyl-2-phenyl-indol-3-yl)-ethanol 
• 1570215-00-7 3,3-difluoro-1,5-dimethyl-2-phenylindolin-2-ol 
• 1224635-42-0 8-methyl-6-phenyl-11H-benzo[a]carbazole 
• 1322697-83-5 1,5-dimethyl-2-phenyl-1H-indole-3-carbaldehyde 
• 1322697-71-1 1,5-dimethyl-2-phenyl-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.

Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines

An Ag-catalyzed cyclization/demethylation of 2-alkynylthio(seleno)anisoles and 2-alkynyldimethylanilines is described and applied for the construction of valuable benzothio(seleno)phenes as well as indoles. Various 2-substituted benzothio(seleno)phenes and indoles were obtained in good to excellent yields under mild reaction conditions with low catalyst loading. An application of this new method is also exemplified with a concise synthesis of a bioactive molecule precursor. Furthermore, a conceivable reaction mechanism is proposed with supports from isotope-exchange experiments.

C2–H Arylation of Indoles Catalyzed by Palladium-Containing Metal-Organic-Framework in γ-Valerolactone

An efficient and selective procedure was developed for the direct C2–H arylation of indoles using a Pd-loaded metal–organic framework (MOF) as a heterogeneous catalyst and the nontoxic biomass-derived solvent γ-valerolactone (GVL) as a reaction medium. The developed method allows for excellent yields and C-2 selectivity to be achieved and tolerates various substituents on the indole scaffold. The established conditions ensure the stability of the catalyst as well as recoverability, reusability, and low metal leaching into the solution.

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.).

A Three-Component Strategy for Benzoselenophene Synthesis under Metal-Free Conditions Using Selenium Powder

An efficient three-component benzoselenophenes formation has been developed from substituted indoles, acetophenones, and selenium powder under metal-free conditions. 2-Aryl indoles played an important role to promote benzoselenophene formation from acetophenone derivatives and selenium powder. One C-C and two C-Se bonds were selectively formed to provide 40 new benzoselenophenes in good yields.

Catalytic Access to Indole-Fused Benzosiloles by 2-Fold Electrophilic C-H Silylation with Dihydrosilanes

A protocol for the catalytic synthesis of indole-fused benzosiloles starting from 2-aryl-substituted indoles and dihydrosilanes is reported. Compared to known procedures, this method does not require prefunctionalized starting materials and, hence, allows for a rapid access to those siloles. The net reaction is a 2-fold electrophilic C-H silylation catalyzed by cationic Ru-S complexes. Both reaction steps were separately investigated, and these results eventually led to the development of a two-step procedure. By preparing new Ru-S complexes with different weakly coordinating anions (WCAs), it is also shown that the latter can have a dramatic influence on the outcome of these reactions. Furthermore, the substrate scope of the new method is discussed.

Silver-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines: Highly efficient synthesis of structurally diverse fluorinated indole derivatives

Highly efficient approaches to obtain structurally diverse fluorinated indole derivatives have been realized through the Ag-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines in the presence of NFSI or Selectfluor. The Royal Society of Chemistry.

Application of FeCl3/diorganyl diselenides to cyclization of o -alkynyl anilines: Synthesis of 3-organoselenyl-(N -methyl)indoles

In this manuscript we described the FeCl3/diorganyl diselenides promoted intramolecular cyclization of o-alkynyl anilines, as an alternative for the construction of functionalized 3-organoselenyl indoles. The cyclization reactions proceeded smoothly at room temperature in the presence of air giving the 3-organoselenyl indoles in good yields. Additionally, the 3-organoselenyl indoles proved to be quite useful as synthetic intermediates for the construction of more functionalized indole units through a selenium-lithium exchange reaction followed by trapping the lithium intermediate with different electrophiles. Georg Thieme Verlag Stuttgart New York.

SILANYLOXYARYL PHOSPHINE LIGAND AND USES THEREOF IN C-N CROSS-COUPLING

The present invention pertains to silanyloxyaryl phosphine ligands of formula (I) and their uses with transition metal catalyst precursors for organic synthesis reactions. More particularly, the present invention pertains to the use of silanyloxyaryl phosphine ligands and with transition metal catalyst precursors in C-N cross-coupling reactions.

Efficient palladium-catalyzed synthesis of substituted indoles employing a new (silanyloxyphenyl)phosphine ligand

The new and easily prepared OTips-DalPhos ligand (L1) offers broad substrate scope at relatively low loadings in the palladium-catalyzed C-N cross-coupling/cyclization of o-alkynylhalo(hetero)arenes with primary amines, affording indoles and related heterocyclic derivatives in high yield.