88039-96-7

Upstream product

• 140-29-4 phenylacetonitrile 
• 635-93-8 5-chlorosalicyclaldehyde 
• 4638-79-3 2-chloro-2-phenylacetaldehyde 
• 100-52-7 benzaldehyde 
• 96-09-3 styrene oxide 
• 1004-99-5 2-chloro-2-phenylethanol 
• 201230-82-2 carbon monoxide 
• 100-44-7 benzyl chloride 
• 103-82-2 phenylacetic acid 
• 7436-90-0 2,2-dibromostyrene 
• 536-74-3 phenylacetylene 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 1333483-14-9 N-methyll-N-(phenylethylnyl)methanesulfonamide 

Downstream Products

• 13130-28-4 6-chloro-3-(2-hydroxyphenyl)-2H-chromen-2-one 
• 1404301-76-3 2-(2-(1,3-dithian-2-ylidene)-2-phenylethyl)-4-chlorophenol 
• 1404301-60-5 6-chloro-3-phenylhydrocoumarin 
• 1404301-95-6 (S)-6-chloro-3-phenylspiro[chroman-2,2'-[1,3]dithiane] 

Relevant academic research and scientific papers

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.

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.

A complete switch of the directional selectivity in the annulation of 2-hydroxybenzaldehydes with alkynes

Controlling reaction selectivity is an eternal pursuit for chemists working in chemical synthesis. As part of this endeavor, our group has been exploring the possibility of constructing different natural product skeletons from the same simple starting mat

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.

Monoamine oxidase (MAO) inhibitory activity: 3-phenylcoumarins versus 4-hydroxy-3-phenylcoumarins

Monoamine oxidase (MAO) is a useful target in the treatment of neurodegenerative diseases and depressive disorders. Both isoforms, MAO-A and MAO-B, are known to play critical roles in disease progression, and as such, the identification of novel, potent a

Palladium catalyzed dehydrogenative arylation of coumarins: An unexpected switch in regioselectivity

A new regioselective α-arylation of coumarins with unactivated simple arenes via a palladium-catalyzed twofold C-H functionalization is devised. This method offers an attractive new approach to synthesis of a wide variety of 3-arylcoumarins from readily accessible starting materials. This journal is The Royal Society of Chemistry 2013.

A general palladium-catalyzed carbonylative synthesis of chromenones from salicylic aldehydes and benzyl chlorides

Cute CO! An interesting and straightforward procedure for the carbonylative synthesis of chromenones from readily available salicylic aldehydes and benzyl chlorides has been developed (see scheme; DPPP=1,3-bis(diphenylphosphino) propane). In the presence of a palladium catalyst, various coumarins were produced in good to excellent yields. Copyright

Synthesis of 3-arylcoumarins through N-heterocyclic carbene catalyzed condensation and annulation of 2-chloro-2-arylacetaldehydes with salicylaldehydes

The condensation reaction of 2-chloro-2-arylacetaldehyde with salicylaldehyde catalyzed by N-heterocyclic carbene (NHC) leading to 3-arylcoumarin was studied. A number of 3-arylcoumarin derivatives were obtained in good to excellent yields via this umpolung reaction. This reaction is facile and experimentally simple and mild.

Deracemization of α-aryl hydrocoumarins via catalytic asymmetric protonation of ketene dithioacetals

An unprecedented catalytic asymmetric protonation of ketene dithioacetals is described. Various racemic α-aryl hydrocoumarin derivatives are transformed into enantioenriched dithioacetal-protected hydrocoumarins in the presence of a chiral Br?nsted acid catalyst. A newly developed phosphoric acid, featuring the 3,5-bis(pentafluorothio)phenyl (3,5-(SF5) 2C6H3) substituent, is introduced. The obtained products can be easily converted into either hydrocoumarins or the corresponding chromans via simple hydrolysis or hydrogenation, respectively.

A convenient synthesis of 3-arylcoumarins from arylacetonitriles

The condensation of salicylaldehydes with various arylacetonitriles catalyzed by anion-exchange resins such as Amberlite IRA 900, leads to the corresponding 3-arylcoumarins in good yields and selectivity.