852171-79-0

Upstream product

• 16419-60-6 2-Methylphenylboronic acid 
• 200055-89-6 4-(4-toluenesulfonyloxy)coumarin 
• 1002130-71-3 methyl 3-[2-(methoxymethoxy)phenyl]propiolate 
• 91-64-5 coumarin 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 3943-94-0 (E)-ethyl 2-hydroxycinnamate 
• 90-02-8 salicylaldehyde 
• 615-37-2 ortho-methylphenyl iodide 
• 420-76-8 tris(2-tolyl)antimony difluoride 
• 1613159-67-3 C₁₆H₁₂O₂ 
• 3943-94-0 3-(2-hydroxy-phenyl)-acrylic acid ethyl ester 
• 210823-54-4 2-methylphenyl(mesityl)iodonium trifluoromethanesulfonate 
• 124-38-9 carbon dioxide 

Relevant academic research and scientific papers

Cascade Synthesis of 4-Arylcoumarins: Pd-Catalyzed Arylations and Cyclizations with (E)-Ethyl 3-(2-Hydroxyaryl)acrylates and Triarylantimony Difluorides

Herein, we describe a simple general method for the synthesis of 4-arylcoumarins using pentavalent organoantimony compounds. The reactions of 3-(2-hydroxyaryl)acrylates with triarylantimony difluorides in the presence of Pd(OAc)2 (10 mol-%) and 2,2'-bipyridyl (10 mol-%) at 80 °C under aerobic conditions afforded 4-arylcoumarins in good-to-excellent yields. This protocol involves a cascade oxidative Heck-type arylation followed by cyclization, with all the aryl groups in the triarylantimony difluoride transferred to the coupling products. Triarylantimony difluorides resulted in better outcomes than those obtained with other pentavalent organoantimony or bismuth compounds.

Photoinduced cyclization of alkynoates to coumarins with N-Iodosuccinimide as a free-radical initiator under ambient and metal-free conditions

An efficient photoinduced strategy for the preparation of coumarins was developed. In the presence of N-iodosuccinimide (NIS) as a free-radical initiator and under LED (380–385 nm) irradiation and metal-free conditions, the reaction of alkynoates underwen

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.

Palladium(II) oxide impregnated on magnetite as a catalyst for the synthesis of 4-arylcoumarins: Via a Heck-arylation/cyclization process

Heck-arylation/cyclization was achieved using heterogeneous palladium(ii) oxide impregnated on magnetite catalyst (2.5 mol%) with a lower catalyst loading than that reported for similar processes. Ethanol was used as a non-toxic and bio-renewable solvent. Good yields were afforded using a broad range of substrates (40-98%). The catalyst could be partially recycled, and analyses confirmed the almost total reduction of palladium(ii) oxide to palladium(0) as well as the iodine poissoning effect, which is the main barrier to complete recyclability.

Synthesis of 4-arylcoumarins via palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamates with diaryliodonium salts

The palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamate ester derivatives by using diaryliodonium(III) salts has been developed. With this method, 4-arylcoumarins were easily prepared in good to excellent yields under base-free conditions

Palladium-catalyzed domino protodecarboxylation/oxidative Heck reaction: Regioselective arylation of coumarin-3-carboxylic acids

A protocol for straightforward and step-economical synthesis of neoflavones from coumarin-3-carboxylic acids is developed. This approach enables controlled protodecarboxylation/regioselective C-H arylation of coumain-3-carboxylic acids in one-pot using a

Vinyl nosylates: An ideal partner for palladium-catalyzed cross-coupling reactions

In a hurry to leave! Nosylates act as an excellent leaving group in various palladium-catalyzed cross-couplings, such as Suzuki, Stille, Heck, and Sonogashira reactions (see scheme). Crystalline, stable, and cheap vinyl and aryl nosylates proved better th

Palladium(II)-catalyzed direct carboxylation of alkenyl C-H bonds with CO2

Pd-catalyzed direct carboxylation of alkenyl C-H bonds with carbon dioxide was realized for the first time. Treatment of 2-hydroxystyrenes and a catalytic amount of Pd(OAc)2 with Cs2CO3 under atmospheric pressure of CO2 afforded corresponding coumarins in good yield. Furthermore, isolation of the key alkenylpalladium intermediate via C-H bond cleavage was achieved. The reaction was proposed to undergo reversible nucleophilic addition of the alkenylpalladium intermediate to CO2.

Palladium-catalyzed oxidative heck coupling reaction for direct synthesis of 4-arylcoumarins using coumarins and arylboronic acids

An efficient protocol for the direct synthesis of 4-arylcoumarins via palladium-catalyzed oxidative Heck coupling reaction of coumarins and arylboronic acids was developed. 4-Arylcoumarins were obtained in moderate to excellent yields, and the reaction also showed tolerance toward functional groups such as hydro, methoxy, diethylamino, nitro, and chloro groups.

Room temperature nickel(II) complexes [(4-MeOC6H 4)Ni(PCy3)2OTs and Ni(PCy3) 2X2]-catalyzed cross-coupling reactions of aryl/alkenyl sulfonates with arylboronic acids

Room temperature nickel(II) complexes [(4-MeOC6H 4)Ni(PCy3)2OTs and Ni(PCy3) 2X2 (X=Cl, Br)]-catalyzed cross-coupling reactions of aryl/alkenyl sulfonates with arylboronic acids are described. The nickel(II) complex (4-MeOC6H4)Ni(PCy3)2OTs proved to be a general catalyst for the Suzuki-Miyaura cross-coupling reactions of aryl sulfonates with arylboronic acids. By limiting the amount of the water in the initial catalytically active Ni(0) species generation stage, Ni(PCy 3)2X2 (X=Cl, Br) could also be efficient catalysts for the cross-coupling reactions a variety of aryl/activated alkenyl tosylates with arylboronic acids. The mild reaction condition, the easy availability of the catalysts and excellent coupling yields make these catalyst systems potentially useful in organic synthesis. Copyright