33603-46-2

Upstream product

• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 122100-93-0 N-(2-iodophenyl)-N-methylcinnamamide 
• 579-10-2 N-acetyl-N-methylaniline 
• 100-51-6 benzyl alcohol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 100-42-5 styrene 
• 93-61-8 N-methyl-N-phenylformamide 
• 100-61-8 N-methylaniline 
• 6273-94-5 N-methyl-N-phenylacrylamide 
• 108-90-7 chlorobenzene 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 615-43-0 2-iodophenylamine 
• 14990-09-1 tert-butyl cinnamate 

Downstream Products

• 18859-20-6 N-methyl-N-phenyl-3-phenylpropanamide 
• 1441636-08-3 1-methyl-3-(1-phenylethyl)indolin-2-one 

Relevant academic research and scientific papers

Visible-Light Mediated Metal-Free 6π-Photocyclization of N-Acrylamides: Thioxanthone Triplet Energy Transfer Enables the Synthesis of 3,4-Dihydroquinolin-2-ones

An efficient thioxanthone-catalyzed triplet energy transfer process for the synthesis of 3,4-dihydroquinolin-2-ones via a 6π-photocyclization is reported. Featuring a rare example of a metal-free formal C(sp2)-H/C(sp3)-H arylation mediated by visible-ligh

Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water

Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient C═C bond formation through aldol condensation. This selective olefination is facilitated by metal-ligand cooperation by the aromatization-dearomatization process operating in the catalytic system. Biorenewable alcohols are used as alkenylation reagents for the challenging α-alkenylation of amides with the highly abundant base metal manganese as a catalyst, which results in water and dihydrogen as the only byproduct, making this catalytic transformation attractive, sustainable, and environmentally benign.

Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines

A series of tetradentate sp2N/sp3N hybrid chiral N4 ligands derived from rigid chiral diamines were synthesized, which enabled the first manganese-catalyzed enantioselective epoxidation of electron-deficient alkenes with hydrogen peroxide (H2O2) as an oxidant. The reaction furnishes enantiomerically pure epoxy amides, epoxy ketones as well as epoxy esters in good yields and excellent enantioselectivities (up to 99.9% ee) with lower catalyst loading. Preliminary studies on structure–activity relationship demonstrated that maintaining comparatively lower electron-donating ability of the sp3N and relatively higher electron-donating ability of sp2N of the N4 ligands is beneficial to getting higher activity and selectivity, thus providing us a new view to understand epoxidation with H2O2. (Figure presented.).

A novel direct synthesis of 3-acyl-4-aryldihydroquinolin-2(1H)-ones via metal-free radical tandem cyclization between N-arylcinnamamides and aldehydes

An efficient metal-free and practical method for the synthesis of disubstituted dihydroquinolin-2(1H)-ones via intermolecular radical tandem addition/cyclization was developed. This method provides a novel and straightforward route to 3-acyl-4-aryldihydro

PhICl2 and wet DMF: An efficient system for regioselective chloroformyloxylation/a-chlorination of alkenes/a,β-unsaturated compounds

PhICl2 in wet DMF was found to form an efficient system for realizing difunctionalization of various alkenes and olefinic derivatives possessing a wide range of functional groups. This novel methodology provides convenient access to either regioselective chloroformyloxylated products or a-chlorinated olefinic products, depending on the type of structure of the original unsaturated starting material. The mechanism of the reaction is proposed and discussed.

Oxidative coupling of alkenes with amides using peroxides: Selective amide C(sp3)-H versus C(sp2)-H functionalization

A new oxidative coupling of unactivated terminal alkenes with amides using peroxides is described, in which mono- and difunctionalization of alkenes are selectively achieved. In this reaction with amides, the chemoselectivity toward the functionalization of the C(sp3)-H bonds adjacent to the nitrogen atom or the functionalization of the carbonyl C(sp2)-H bonds across alkenes relies on the reaction conditions. This journal is

Copper-catalyzed bis(methoxycarbonyl)carbene reactions of α,β-unsaturated carboxamides

The [Cu(acac)2]-catalyzed reactions of α,β- unsaturated carboxamides with dimethyl diazomalonate yielded dihydrofuran derivatives by a 1,5-electrocyclic reaction at C(β), and butadiene derivatives by carbene addition reaction at C(α) (Schemesa

An efficient and general method for the heck and buchwald-hartwig coupling reactions of aryl chlorides

The β-diketiminatophosphane Pd complex acted as a powerful catalyst for the Heck coupling of aryl chlorides with alkenes. Various aryl and heteroaryl chlorides were coupled efficiently under relatively mild conditions. Furthermore, this catalytic system also proved to be highly active in the Buchwald-Hartwig coupling of deactivated and sterically hindered aryl chlorides at room temperature.

Palladium(II)-catalyzed catalytic aminocarbonylation and alkoxycarbonylation of terminal alkynes: Regioselectivity controlled by the nucleophiles

The aminocarbonylation and alkoxycarbonylation reactions of terminal alkynes took place smoothly and efficiently using a catalyst system Pd(OAc) 2-dppb-p-TsOH-CH3CN-CO under relatively mild experimental conditions. The catalytic system was tested and optimized using two different nucleophiles: alcohols and amines. Phenylacetylene (1a) was considered as an alkyne along with diisobutylamine (2b1) andmethanol (2c1) as nucleophiles. The results showed significant differences in the conversion of 1a and in the selectivity towards the gem or trans unsaturated esters or amides with these nucleophiles. The effects of the type of palladium catalysts, the type of ligands, the amount of dppb and the solvents were carefully studied. With diisobutylamine (2b1), excellent regioselectivity towards the 2-acrylamides (gem isomer, 3ab1) was almost always observed, while trans-α,β-unsaturated esters 4ac1 was the predominant product with methanol (2c1) as a nucleophile. This remarkable sensitivity in the selectivity of the reaction indicates two different possible mechanistic pathways for these carbonylation reactions. Copyright

Cathodic reduction of N-(2-iodophenyl)-N-alkylcinnamides: A novel sequential electrochemical radical cyclisation and hydroxylation

In recent years, intramolecular aryl radical cyclisation has emerged as a useful route for the synthesis of benzannulated heterocycles and carbocycles. The aryl radicals are generated in situ from aryl halides (iodides or bromides) with tributylstannyl hydride-AIBN, SmI2, Co(I) or under photochemical conditions. The present work envisages the generation of aryl radicals by cathodic reduction of the carbon-iodine bond of N-(2-iodophenyl)-N-alkylcinnamides and their intramolecular cyclisation. The cathodic reduction of N-(2-iodophenyl)-N-alkyl-cinnamides under deaerated conditions in DMF gave 1-alkyl-3-benzylindolin-2-ones regioselectively and in the presence of oxygen yielded surprisingly 1-alkyl-3-hydroxy-3-benzylindolin-2-ones. Both these products were formed by a 5-exo-trig process in good yields. A mechanism for the formation of the products has been proposed through the use of cyclic voltammetry, coulometry and controlled-potential electrolysis as well as deuterium labelling.