16807-67-3

Upstream product

• 140-29-4 phenylacetonitrile 
• 1761-61-1 5-bromosalicyclaldehyde 
• 103-82-2 phenylacetic acid 
• 103-80-0 phenylacetyl chloride 
• 4638-79-3 2-chloro-2-phenylacetaldehyde 
• 100-52-7 benzaldehyde 
• 96-09-3 styrene oxide 
• 1004-99-5 2-chloro-2-phenylethanol 
• 536-74-3 phenylacetylene 
• 1333483-14-9 N-methyll-N-(phenylethylnyl)methanesulfonamide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 19063-55-9 6-bromo-2H-chromen-2-one 
• 62-53-3 aniline 
• 1074-12-0 phenylglyoxal hydrate 

Downstream Products

• 1404301-75-2 2-(2-(1,3-dithian-2-ylidene)-2-phenylethyl)-4-bromophenol 
• 1404301-59-2 6-bromo-3-phenylhydrocoumarin 
• 1404301-93-4 (S)-6-bromo-3-phenylspiro[chroman-2,2'-[1,3]dithiane] 

Relevant academic research and scientific papers

Efficient synthesis of 3-substituted coumarins

The Mukaiyama's esterification protocol, using 2-chloro-1-methylpyridinium iodide-triethylamine reagent, has been successfully exploited to provide rapid access to a variety of 3-substituted coumarins in satisfactory yields.

Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins

A facile and efficient synthetic approach to various valuable 3-aryl- and 3-aroylcoumarins by the direct arylation and aroylation of coumarins with glyoxals in a metal-free manner is presented. The aryl glyoxal is for the first time recognized to serve as an aryl surrogate in addition to its role as an aroyl transfer reagent via a simple switch in reaction conditions. The approach accommodates a broad substrate scope and high yields of the two types of cross-coupling reactions starting from identical starting materials.

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.

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.

Conversion of 2-methoxychalcones into 3-phenylcoumarins

A new approach to the synthesis of 3-phenylcoumarins from 2-methoxychalcone is presented.This conversion constitutes an interesting way of reorganising the central C3-unit of the chalcone.