5667-75-4

Upstream product

• 106-49-0 p-toluidine 
• 101-97-3 Ethyl 2-phenylethanoate 
• 22065-57-2 ethyl 2-phenyldiazoacetate 

Downstream Products

• 93-89-0 benzoic acid ethyl ester 

Relevant academic research and scientific papers

Method for realizing insertion reaction of diazo ester compound and aniline molecule N-H through photocatalytic micro-channel

A homogeneous solution containing the aniline represented by the formula N, a derivative thereof and a diazo ester compound shown H is pumped into a microchannel reaction device with a light source to react to obtain I phenyl II benzene ethyl acetate deri

Metal-Free Insertion of Sulfoxonium Ylides into Arylamines in Water

Carbenoid-based N-H insertions have undergone significant development with respect to C-N bond formation in recent years. However, the existing methods suffer from unstable starting materials, expensive metal catalysts and organic solvents. Herein, insertion of sulfoxonium ylides into arylamines under metal-free conditions has been developed. The method employs water as solvent at mild temperature and is amenable to the late-stage modification of structurally complex bioactive compounds.

Carbene X[sbnd]H bond insertions catalyzed by copper(I) macrocyclic pyridine-containing ligand (PcL) complexes

A catalytic system comprising copper(I) and macrocyclic pyridine-containing ligands (Pc-L) proves capable of promoting carbene Si[sbnd]H bond insertions using diazo compounds as the carbene source. This catalytic system showed broad scope and a remarkable robustness as indicated by high TON numbers (up to 30000). Moreover, the use of enynones as carbene sources proved also feasible in hydrosilane insertion using this catalytic system. Finally, the insertion in O[sbnd]H and N[sbnd]H bonds of phenols and anilines, respectively, has been also demonstrated.

Phosphine ligands stabilized Cu(I) catalysts for carbene insertion into the N-H bond

Phosphine ligands have been successfully used along with Cu(I) for several catalytic reactions, nevertheless these ligands were less explored relatively for carbene involved reactions owing to the formation of carbene-phosphine ylides. In this report we successfully used three different phosphine stabilized Cu(I) complexes (1-3) as catalysts for chemoselective carbene insertion into the N-H bond of different aromatic amines over the formation of olefin (carbene dimerized product). In order to understand the substrate scope, different α-diazo esters have been reacted with large number of amines and all the reactions produced reasonably good yields under normal experimental conditions (38 examples). All the carbene inserted products have been isolated by column chromatography and fully characterized using standard spectroscopic techniques without any ambiguities. Several control reactions have been conducted in order to understand the importance of the type of phosphine ligands used in the catalysts 1-3 and found that without these catalysts we observed less selectivity (more of olefin as the product over N-H inserted product) and low yield. From this present study, it can be noted that the rigid framework phosphine ligands would be the better choice for carbene chemistry. The results obtained from the current studies would inspire chemists to develop more novel Cu(I)-phosphine catalysts for carbene related reactions including asymmetric versions in the near future.

Palladium-catalyzed carbenoid based N-H bond insertions: Application to the synthesis of chiral α-amino esters

A highly efficient palladium-catalyzed carbenoid based N-H bond insertion has been developed. The α-amino esters were obtained in high isolated yields. Moreover, by choosing a suitable chiral auxiliary, stereoselective Pd-catalyzed N-H insertion has been realized. The chiral α-amino esters were obtained in high yields (up to 91%) and with excellent diastereoselectivities (d.r. > 19:1). The Royal Society of Chemistry.

Ruthenium-catalyzed one-pot carbenoid N-H insertion reactions and diastereoselective synthesis of prolines

Aryl- and aliphatic-substituted 3-hydroxyprolines and various other amino esters are conveniently prepared by [RuCI2(p-cymene)] 2-catalyzed one-pot intramolecular and intermolecular carbenoid N-H insertion reactions, respectively, and the prolines are formed with high diastereoselectivities. The catalytic reactions are tolerant toward air/moisture, and the product yields are insensitive to the organic solvents used.