5469-90-9

Upstream product

• 536-74-3 phenylacetylene 
• 100-61-8 N-methylaniline 
• 122-78-1 phenylacetaldehyde 
• 103-80-0 phenylacetyl chloride 
• 40669-47-4 N-methyl-N,2-diphenylacetamide 
• 100-42-5 styrene 
• 98-95-3 nitrobenzene 
• 103-64-0 bromostyrene 
• 121-73-3 3-Nitrochlorobenzene 
• 30649-18-4 cinnamic alcohol 
• 109-89-7 diethylamine 
• 100-51-6 benzyl alcohol 
• 6314-97-2 1,1-diethoxy-2-phenylethane 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 92245-81-3 N-Benzolsulfonyl-N'-methyl-N'-phenyl-formamidin 

Relevant academic research and scientific papers

Iron-Catalyzed Synthesis of 2-Aminofurans from 2-Haloketones and Tertiary Amines or Enamines

The selective synthesis of heterocycles from readily available substrates and catalyzed by an abundant and environmental benign catalyst continues to be an attractive topic. In this communication, we report an interesting protocol for the synthesis of 2-aminofurans. Starting from 2-haloketones and tertiary amines, with abundant iron salt as the catalyst, various 2-aminofurans were produced in good yields. Control experiments were performed to understand the reaction pathway. Based on the identified reaction pathway, the substrates for this transformation can be extended from tertiary amines to enamines and even with better final yields. Finally, a formal three-component reaction can also be realized by forming the enamines in-situ from aldehydes and amines.

Palladium-Catalyzed Methylation of Nitroarenes with Methanol

A procedure for the synthesis of N-methyl-arylamines directly from nitroarenes using methanol as green methylating agent was developed. The key to success is the use of a specific catalyst system consisting of palladium acetate and the ligand 1-[2,6-bis(isopropyl)phenyl]-2-[tert-butyl(2-pyridinyl)phosphino]-1H-Imidazole (L1). The generality of this protocol is demonstrated in the synthesis of more than 20 N-methyl-arylamines under comparably mild conditions. Combining this novel methodology with subsequent coupling processes using the same catalyst allows for efficient diversification of aromatic nitro compounds to a broad variety of amines including drug molecules.

Method for synthesizing enamine under catalysis of palladium imine complex containing pyridine ligands

The invention relates to a method for synthesizing enamine under catalysis of a palladium imine complex containing pyridine ligands. The method comprises steps as follows: phenylacetylene and secondary amine are taken as raw materials, the palladium imine

Method for preparing enamine compound by catalyzing phenylacetylene and utilizing hydroamination reaction

The invention provides a method for preparing an enamine compound by catalyzing phenylacetylene and utilizing the hydroamination reaction. The method is characterized by comprising the steps that thephenylacetylene and secondary amine are taken as raw mat

Iridium-PPh3 Catalysts for Conversion of Amides to Enamines

Studies on the deactivation mechanism of the reaction of N,N-dialkylamides with TMDS catalyzed by Vaska's complex, IrCl(CO)(PPh3)2 (1a), triggered the discovery of highly active Ir-PPh3 catalysts: Photochemically activated

An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides

A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).

Coupling of C(sp3)-H bonds with C(sp2)-O electrophiles: mild, general and selective

Herein is reported the mild and general coupling of amine/ether C(sp3)-H bonds with various kinds of C(sp2)-O electrophiles with high selectivity and efficiency. Valuable allylic/benzylic amines are generated in moderate to excellent yields. The utility of this transformation is demonstrated by a broad substrate scope (>50 examples), good functional group tolerance and facile product modification.

Transformation of Amides into Highly Functionalized Triazolines

Triazoles and triazolines are important classes of heterocyclic compounds known to exhibit biological activity. Significant focus has been given to the development of synthetic approaches for the preparation of triazoles, and they are today easily obtainable through a large variety of protocols. The number of synthetic procedures for the formation of triazolines, on the other hand, is limited and further research in this field is required. The protocol presented here gives access to a broad scope of 1,4,5-substituted 1,2,3-triazolines through a one-pot transformation of carboxamides. The two-step procedure involves a Mo(CO)6-catalyzed reduction of tertiary amides to afford the corresponding enamines, followed by in situ cycloaddition of organic azides to form triazolines. The amide reduction is chemoselective and allows for a wide variety of functional groups such as esters, ketones, aldehydes, and imines to be tolerated. Furthermore, a modification of this one-pot procedure gives access to the corresponding triazoles. The chemically stable amide functionality is demonstrated to be an efficient synthetic handle for the formation of highly substituted triazolines or triazoles.

Mild reductive functionalization of amides into N-sulfonylformamidines

The development of a protocol for the reductive functionalization of amides into N-sulfonylformamidines is reported. The one-pot procedure is based on a mild catalytic reduction of tertiary amides into the corresponding enamines by the use of Mo(CO)6 (molybdenum hexacarbonyl) and TMDS (1,1,3,3-tetramethyldisiloxane). The formed enamines were allowed to react with sulfonyl azides to give the target compounds in moderate to good yields.

Inverse electron demand hetero-Diels-Alder reaction in preparing 1,4-benzodioxin from o-quinone and enamine

A process for synthesizing 1,4-benzodioxin, through oxidation of a phenol to an o-quinone followed by treatment with an enamine, has been developed. Adduct stereochemistry is found to be retained via this one-pot reaction. The method uses hypervalent iodine reagent under mild conditions and is compatible with a wide scope of phenols and enamines.