93696-64-1

Upstream product

• 93696-61-8 3-bromo-6-methyl-4-p-tolyl-3,4-dihydrocoumarin 
• 1239896-43-5 4-bromo-6-methyl-2H-chromen-2-one 
• 5142-75-6 tri(p-tolyl)bismuth 
• 635757-40-3 6-methyl-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate 
• 81652-53-1 (2-hydroxy-4-methylphenyl)(p-tolyl)methanone 
• 105-53-3 diethyl malonate 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 624-31-7 4-tolyl iodide 
• 1359857-02-5 3-(2-hydroxy-5-methyl-phenyl)-acrylic acid ethyl ester 
• 5720-05-8 4-methylphenylboronic acid 
• 92-48-8 6-methylcoumarin 
• 51069-75-1 4-chloro-6-methyl-2H-chromen-2-one 
• 93500-99-3 2,3-Dibromo-3-p-tolyl-propionic acid p-tolyl ester 
• 93696-66-3 α,β-dibromo-p-methylhydrocinnamic acid chloride 

Relevant academic research and scientific papers

Preparation method of 4-aryl coumarin and derivative of 4-aryl coumarin

The invention relates to a preparation method of 4-aryl coumarin and a derivative of 4-aryl coumarin. The preparation method comprises the following steps: heating reactants a diaryl ketone derivativeand diethyl malonate in a modified DBU and Pd/C catalytic system by a one-step method to obtain the product. The preparation method has the advantages that reaction rate is high, reaction can be completed in several hours, reaction selectivity is extremely high, few or no by-product is generated, and target product yield is high, powerful improvement on a present preparation method of 4-aryl coumarin and the derivative of 4-aryl coumarin is achieved, and the industrialization prospect is promising.

Palladium catalyzed Heck-arylation/cyclization cascade: An environmentally benign and efficient synthesis of 4-arylcoumarins in water

An environmentally benign and efficient approach for the synthesis of 4-arylcoumarins from ortho-hydroxy cinnamate ester derivatives with aryl iodides was developed in water under aerobic conditions. This transformation proceeds through a palladium catalyzed Heck-arylation/cyclization cascade reaction. The present protocol features a wide substrate scope and readily available starting materials to afford the desired products in high to excellent yields.

Heck and oxidative boron Heck reactions employing Pd(II) supported amphiphilized polyethyleneimine-functionalized MCM-41 (MCM-41@aPEI-Pd) as an efficient and recyclable nanocatalyst

A novel nanocatalyst was developed based on covalent surface functionalization of MCM-41 with polyethyleneimine (PEI) using [3-(2,3-Epoxypropoxy)propyl] trimethoxysilane (EPO) as a cross-linker. Amine functional groups on the surface of MCM-41 were then conjugated with iodododecane to render an amphiphilic property to the catalyst. Palladium (II) was finally immobilized onto the MCM-41@PEI-dodecane and the resulted MCM-41@aPEI-Pd nanocatalyst was characterized by FT-IR, TEM, ICP-AES and XPS. Our designed nanocatalyst with a distinguished core-shell structure and Pd2+ ions as catalytic centers was explored as an efficient and recyclable catalyst for Heck and oxidative boron Heck coupling reactions. In Heck coupling reaction, the catalytic activity of MCM-41@aPEI-Pd in the presence of triethylamine as base led to very high yields and selectivity. Meanwhile, the MCM-41@aPEI-Pd as the first semi-heterogeneous palladium catalyst was examined in the C-4 regioselective arylation of coumarin via the direct C-H activation and the moderate to excellent yields were obtained toward different functional groups. Leaching test indicated the high stability of palladium on the surface of MCM-41@aPEI-Pd as it could be recycled for several runs without significant loss of its catalytic activity.

Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents

Cross-coupling reactions of differently substituted 4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2-4 h conditions. The utility of the methodology was explored in the synthesis of a few natural occurring neoflavones (3.27-3.30). In addition, the 4-arylcoumarin 3.1 product is a useful precursor for the preparation of (R)-tolterodine.

A convenient solid-phase synthesis of coumarins by TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes

TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocou

Palladium-catalyzed synthesis of 4-arylcoumarins using triarylbismuth compounds as atom-Efficient multicoupling organometallic nucleophiles

Triarylbismuth compounds have been cross-coupled as atomefficient multicoupling organometallic nucleophiles with. 4bromo- and 4- (trifluoromethylsulfonyloxy)coumarins under palladium catalysis conditions. These reactions afforded an array of 4-arylcoumari

Palladium-catalyzed Suzuki-Miyaura couplings of potassium aryl trifluoroborates with 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one

Pd(PPh3)4 catalyzed Suzuki-Miyaura cross-coupling reactions of 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one with various potassium aryl trifluoroborates afforded the corresponding 4-substituted coumarins or 4-substituted quino

Rh(I)-catalyzed cross-coupling reactions of alkenyl tosylates with potassium aryltrifluoroborates

RhCl(PPh3)3/DPPF was successfully employed as an efficient catalyst in the Suzuki-Miyaura cross-coupling reactions of potassium aryltrifluoroborates with alkenyl tosylates, affording the corresponding products in good to excellent yi

Synthesis of 3-Arylcoumarins, Thiacoumarins and Carbostyrils

3-Arylcarbostyrils (2a-f), coumarins (2g-j) and thiacoumarin (2k) have been prepared by a generalised method from α,β-dibromohydrocinnamoyl derivatives (1a-k).The intermediate dihydrocoumarins and dihydrocarbostyrils (3, Y = O, NH) have been prepared which on acid treatment furnish 2.However, treatment of 3 with a base affords the 4-arylcoumarins and carbostyrils (4).