87587-25-5

Upstream product

• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 1066-54-2 trimethylsilylacetylene 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 15111-14-5 2-iodo-N-(phenylmethylene)-benzenamine 
• 615-43-0 2-iodophenylamine 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 87587-48-2 tris(trimethylsilylethynyl)aluminum 
• 87587-23-3 N-benzyl-N-phenyl-O-(trimethylsilyl)hydroxylamine 

Downstream Products

• 1616706-98-9 N-benzyl-2-((4-methoxyphenyl)ethynyl)aniline 
• 1380395-13-0 N-benzyl-2-((4-methylphenyl)ethynyl)aniline 
• 1186509-61-4 1-benzyl-1H-indazole-3-carbaldehyde 

Relevant academic research and scientific papers

Indazole 2-oxides compound and method for preparing indazole 2-oxides compound for providing a nitrogen heterocyclic compound used as a precursor for drugs

Provided is a method for preparing an indazole 2-oxides compound, which comprises the step of: performing a cyclization reaction on 2-alkynyl aniline compound and tert-butylnitrite represented by formula (1) in the presence of bis(dibenzylideneacetone) palladium so as to produce an indazole 2-oxides compound, in which, in the formulae (1) and (2), R1 , R2 , R3 and R4 are each hydrogen, halogen or alkyl group; X1 represents an alkyl group, a first chemical structure, a second chemical structure or a third chemical structure where T1 , T2 , T3 , T4 and T5 are each hydrogen, halogen, alkoxy group, or alkyl group; X2 represents hydrogen, cycloalkyl group, alkyl group, alkenyl group, thienyl group, unsubstituted phenyl group, or substituted phenyl group, where the substituent is selected from the group consisting of an alkyl group, an alkoxy group, a halogen, a haloalkyl group, -CN, or -NO2.

Photoinduced synthesis of fluorinated dibenz[: B, e] azepines via radical triggered cyclization

A simple, mild and efficient approach to access fluorinated dibenz[b,e]azepines via visible-light photoredox catalysis is presented. Inexpensive and commercially available fluoroalkyl anhydrides in concert with pyridine N-oxide are employed as the source

Electrochemical Difluoromethylarylation of Alkynes

An unprecedented radical difluoromethylarylation reaction of alkynes has been developed by discovering a new difluoromethylation reagent, CF2HSO2NHNHBoc. This air-stable and solid reagent can be prepared in one step from commercially available reagents CF2HSO2Cl and NH2NHBoc. The CF2H radical, generated through ferrocene-mediated electrochemical oxidation, participates in an unexplored alkyne addition reaction followed by a challenging 7-membered ring-forming homolytic aromatic substitution step to afford fluorinated dibenzazepines.

Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides

An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo

Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides

We report a highly robust, general and stereoselective method for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using PdCl2(PhCN)2 as the catalyst. The transformation involves a stereo- and regioselective chloropalladation of an internal alkyne to generate a nucleophilic vinyl PdII species, which then undergoes an intramolecular cross-coupling with a carbamoyl chloride. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, and is readily scalable. The products obtained from this reaction are formed with >95:5 Z:E selectivity in nearly all cases and can be used to access biologically relevant oxindole cores. Through combined experimental and computational studies, we provide insight into stereo- and regioselectivity of the chloropalladation step, as well as the mechanism for the C-C bond forming process. Calculations provide support for a mechanism involving oxidative addition into the carbamoyl chloride bond to generate a high valent PdIV species, which then undergoes facile C-C reductive elimination to form the final product. Overall, the transformation constitutes a formal PdII-catalyzed intramolecular alkyne chlorocarbamoylation reaction.

Synthesis of 3,4-fused 2-quinolones from an (ortho-aminophenyl)propiolate via sequential cycloaddition/lactam formation

An N-phthalimide-protected (ortho-aminophenyl)propiolate was prepared by the carboxylation of the corresponding silylalkyne precursor with carbon dioxide. The obtained propiolate was further transformed to various 3,4-fused 2-quinolones via cycloadditions and subsequent deprotection/lactam formation.

An efficient approach to 1,2,3-trisubstituted indole via rhodium catalyzed carbene Csp3-H bond insertion

A method for convenient synthesis of N-alkyl-2-aryl-indole-3-carbaldehyde has been described. A variety of highly valuable indolyl aldehydes have been prepared through this method. Electron donating groups on both aromatic rings (anilinyl and benzyl) facilitate the formation of the desired products. A benzylic C-H insertion by rhodium carbene is the key step for this transformation. This journal is

Development of an Enyne Metathesis/Isomerization/Diels-Alder One-Pot Reaction for the Synthesis of a Novel Near-Infrared (NIR) Dye Core

N-Alkyl-N-allyl-2-alkynylaniline derivatives undergo a tandem ring-closing enyne metathesis/isomerization/Diels-Alder cycloaddition sequence in the presence of a second-generation Grubbs catalyst and dienophiles. In practice, the acyclic enyne in the pres

Preparation of triazoloindoles via tandem copper catalysis and their utility as α-imino rhodium carbene precursors

3-Sulfonyl[1,2,3]triazolo[4,5-b]indoles were efficiently prepared via a tandem catalysis process involving intramolecular ligand stabilized CuAAC and Cu-catalyzed C-N coupling. The obtained 3-sulfonyl[1,2,3]triazolo[4,5-b]indoles could be utilized as α-im

Pd(ii)-catalyzed ligand controlled synthesis of methyl 1-benzyl-1H-indole- 3-carboxylates and bis(1-benzyl-1H-indol-3-yl)methanones

A simple change of ligand and solvent allows controlled, effective switching between cyclization-carbonylation and cyclization-carbonylation- cyclization-coupling (CCC-coupling) reactions of 2-alkynylanilines catalyzed by palladium(ii). The use of a [Pd(tfa)2(box)] catalyst in iPrOH afforded symmetrical ketones bearing two indoles in good yields; replacing the catalyst and solvent with Pd(tfa)2 and DMSO-MeOH led to the formation of methyl 1-benzyl-1H-indole-3-carboxylates in good yields. This journal is