172887-18-2

Upstream product

• 496-15-1 1-indoline 
• 623-12-1 4-chloromethoxybenzene 
• 120-72-9 indole 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 777092-51-0 1-(4-methoxy-phenyl)-2,3-dihydro-1H-indole-5-carbaldehyde 
• 1443380-55-9 C₂₅H₃₃N₃O₅ 
• 777092-62-3 1-(4-methoxy-phenyl)-5-styryl-2,3-dihydro-1H-indole 

Relevant academic research and scientific papers

Dialkylterphenyl Phosphine-Based Palladium Precatalysts for Efficient Aryl Amination of N-Nucleophiles

A series of 2-aminobiphenyl palladacycles supported by dialkylterphenyl phosphines, PR2Ar′ (R=Me, Et, iPr, Cyp (cyclopentyl), Ar′=ArDipp2, ArXyl2f, Dipp (2,6-C6H3-(2,6-C6H3-(CHMe2)2)2), Xyl=xylyl) have been prepared and structurally characterized. Neutral palladacycles were obtained with less bulky terphenyl phosphines (i.e., Me and Et substituents) whereas the largest phosphines provided cationic palladacycles in which the phosphines adopted a bidentate hemilabile k1-P,η1-Carene coordination mode. The influence of the ligand structure on the catalytic performance of these Pd precatalysts was evaluated in aryl amination reactions. Cationic complexes bearing the phosphines PiPr2ArXyl2 and PCyp2ArXyl2 were the most active of the series. These precatalysts have demonstrated a high versatility and efficiency in the coupling of a variety of nitrogen nucleophiles, including secondary amines, alkyl amines, anilines, and indoles, with electronically deactivated and ortho-substituted aryl chlorides at low catalyst loadings (0.25–0.75 mol % Pd) and without excess ligand.

Sustainable ppm level palladium-catalyzed aminations in nanoreactors under mild, aqueous conditions

A 1?:?1 Pd?:?ligand complex, [t-BuXPhos(Pd-π-cinnamyl)]OTf, has been identified as a highly robust pre-catalyst for amination reactions leading to diarylamines, where loadings of metal are typically at 1000 ppm Pd, run in water at temperatures between rt and 45 °C. The protocol is exceptionally simple, is readily scaled, and compares very favorably vs. traditional amination conditions. It has also been shown to successfully lead to key intermediates associated with several physiologically active compounds.

"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.

Combined experimental/theoretical study of D-glucosamine promoted Ullmann-type C-N coupling catalyzed by copper(I): Does amino really count?

Ullmann type C-N coupling reaction catalyzed by copper(I) with D-glucosamine derivatives as promoters was studied by means of combined experimental/theoretical investigation. The catalytic role of D-glucosamine was addressed. In contrast with previous speculations, the amino group may not count in the catalytic cycle in which the oxidative addition/reductive elimination mechanism works. Experimental results are in good agreement with theoretical findings. Extensive work indicates the wide applicability of the C-N coupling strategy exploited in this work.

Solvent- and ligand-free palladium-catalyzed amination of aryl halides

An environmentally friendly and economically favorable approach to the formation of C-N bonds is presented. The methodology is particularly interesting in that the reaction is realized under both solvent- and ligand-free conditions and involves the use of

Solvent-free, microwave-assisted N-arylation of indolines by using low palladium catalyst loadings

Indoline-based compounds are abundant in nature, and the indoline skeleton is an often-encountered scaffold in a range of biologically active alkaloids, pharmaceutically active compounds, and functional molecules (e.g., sensitizers for solar cells). The wide range of uses warrants further interest in the structural modification of this class of compounds. A series of substituted N-aryl indolines is prepared by a solvent-free, palladium-catalyzed procedure. The procedure requires only low loadings of catalyst, uses microwave irradiation, and starts from commercially available substrates. The method proceeds in good yields and in short reaction times with aryl bromides, chlorides, and iodides, also on 2-substituted indolines. The combination of solvent-free methods with microwave heating will further increase in importance in the search for more environmentally acceptable synthesis methods. Copyright

Novel synthetic strategy of N-arylated heterocycles via sequential palladium-catalyzed intra- and inter-arylamination reactions

The use of an in situ generated Pd(0) catalyst associated to N,N′-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as a ligand and t-BuONa as the base for sequential intra- followed by intermolecular aryl animation is described. The method has been applied to the synthesis of N-arylated five-, six- and seven-membered nitrogen heterocycles.

Substituent-dependent photoinduced intramolecular charge transfer in N-aryl-substituted trans-4-aminostilbenes

The photochemical behavior of trans-4-(N-arylamino)stilbene (1, aryl = 4-substituted phenyl) in solvents more polar than THF is strongly dependent on the substituent in the N-aryl group. This is attributed to the formation of a twisted intramolecular char