23000-31-9

Upstream product

• 103-82-2 phenylacetic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 860208-04-4 2-methyl-phenanthrene-9-carboxylic acid 
• 140-29-4 phenylacetonitrile 
• 64-19-7 acetic acid 
• 1555-80-2 phenylacetic anhydride 
• 95517-94-5 6-Methyl-3-phenyl-5,6,7,8-tetrahydro-chromen-2-one 
• 93696-59-4 3-bromo-6-methyl-4-phenyl-3,4-dihydrocoumarin 
• 93501-24-7 2-Bromo-3,3-diphenyl-propionic acid p-tolyl ester 
• 93501-26-9 2-Bromo-3-phenyl-3-p-tolyl-propionic acid p-tolyl ester 
• 93501-28-1 2-Bromo-3-(4-chloro-phenyl)-3-phenyl-propionic acid p-tolyl ester 
• 93500-97-1 p-cresyl α,β-dibromohydrocinnamate 
• 122778-73-8 3-(2-Hydroxy-5-methylphenyl)-2-phenylcyclopropenon 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 1253967-62-2 6-bromomethyl-3-phenylcoumarin 
• 1404302-04-0 (S)-6-methyl-3-phenylspiro[chroman-2,2'-[1,3]dithiane] 
• 1404301-63-8 6-methyl-3-phenylhydrocoumarin 
• 1387531-03-4 6-formyl-3-phenylcoumarin 

Relevant academic research and scientific papers

Chlorophyll-catalyzed photochemical regioselective coumarin C-H arylation with diazonium salts

This communication describes the development of a mild method for the cross-coupling of the C3-position of coumarin with an array of diazonium salts mediated by chlorophyll as a biocatalyst via visible light catalysis. A natural pigment such as chlorophyll is used as a green photosensitizer and environmentally benign catalyst. This general and easy procedure provides a transition-metal-free alternative for the formation of 3-aryl coumarin derivatives at room temperature with good to excellent yields. This journal is

Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes

A highly efficient and straightforward synthesis of diversely substituted coumarins from ynamides and salicylaldehydes in the presence of Zn(II) catalyst has been developed. The sulfonamide moiety of ynamides was successfully recycled in this process, serving as an effective traceless directing group for high regioselectivity in the bond-forming event. The advantages of this protocol are good functional group tolerance, broad substrate scope, simple and high-yielding reaction, recovery/reuse of the sulfonamides, low catalyst loading of inexpensive catalyst, and, by these merits, a more cost-effective and greener process.

Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: Regioselective synthesis of 3-arylcoumarins

We present the first example of sustainable, intuitive, highly regioselective, visible-light-driven copper catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones with terminal alkynes for the preparation of 3-arylcoumarins at room temperature. This operationally simple methodology has been successfully applied to a wide range of N-tosylhydrazones and alkynes (49 examples), and proceeds well to afford biologically active compounds, such as monoamine oxidase B (MAO-B) inhibitor and horseradish peroxidase (HRP) inhibitor, in satisfactory yields under mild conditions. Furthermore, mechanistic studies suggest that the reaction proceeds via a copper(ii)-superoxo or -peroxo complex mediated oxidative annulation of terminal alkynes, as evidenced by 18O2 isotopic-labelling experiments.

Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides using N-formylsaccharin as a CO surrogate

A convenient and highly efficient Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides to afford the corresponding 3-arylcoumarins in good to excellent yields has been developed. Importantly, the protocol utilizes a commercially available, low cost, solid and easy to handle N-formylsaccharin as an alternative to the highly toxic CO gas.

Copper-Catalyzed Preparation of 2-Aryl-3-cyanobenzofurans with Bright Blue Photoluminescence

Copper-catalyzed cascade synthesis of 2-aryl-3-cyanobenzofurans from o-hydroxybenzaldehydes and arylacetonitriles in the presence of copper acetate and sodium methoxide is reported. The synthesized 2-aryl-3-cyanobenzofurans emit bright blue under UV light with a quantum yield up to 88.9%. (Chemical Equation Presented).

Regioselective C-3 arylation of coumarins with arylhydrazines via radical oxidation by potassium permanganate

An efficient protocol for oxidative C-3 arylation of coumarins with arylhydrazine has been developed using potassium permanganate as an oxidant. The arylated coumarins with different electronic properties were obtained in moderate to good yields. The deve

KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids

An efficient protocol for KMnO4/AcOH-mediated dehydrogenative direct radical arylation of coumarins with arylboronic acids to afford 3-arylcoumarin derivatives is described. A similar reaction system is also applicable to the 3-arylation of quinolinone derivatives. These KMnO4/AcOH-mediated coupling reactions occur regioselectively at the C3 position of coumarins and quinolinones. Some notable features of this method are high efficiency, moderate to good yield, and a broad group tolerance.

Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions

A facile regioselective metal-free direct α-arylation of coumarins and 2-pyridones is achieved by the reaction of coumarins and 2-pyridones with phenylhydrazine in good yields. The reaction proceeds at room temperature under mild conditions using inexpensive reagents and without the need for step intensive activating groups. The methodology is operationally simple, practically viable and also allows the coupling of similar nitrogen heterocycle aza-coumarins without prerequisite N-protection.

Base-promoted synthesis of coumarins from salicylaldehydes and aryl-substituted 1,1-dibromo-1-alkenes under transition-metal-free conditions

Facile synthesis of coumarin via the tandem reaction of salicylaldehyde with aryl-substituted 1,1-dibromo-1-alkene was developed. This new protocol proceeds smoothly under mild and transition-metal-free conditions, it allows rapid access to coumarins containing various heteroatoms that are more difficult to prepare by traditional methods. Based on the isolated intermediate of 4-(diethylamino)-3-phenylchroman-2-one and detailed mechanistic studies, a credible tandem pathway was proposed.

Versatile palladium-catalyzed C-H olefination of (hetero)arenes at room temperature

The room-temperature oxidative C-H/C-H cross-couplings between (hetero)arenes and alkenes, coumarins or quinones have been reported by using a highly electrophilic palladium species [Pd(TFA)2], generated in situ from Pd(OAc)2and TFA, as the catalyst and cheap (NH4)2S2O8as the oxidant under air.