15185-05-4

Upstream product

• 79-37-8 oxalyl dichloride 
• 24892-80-6 2-(1-phenylvinyl)anisole 
• 61198-52-5 3,4-dihydro-4-phenyl-2H-1-benzopyran-2-one 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 108-95-2 phenol 
• 75-36-5 acetyl chloride 
• 131575-51-4 Trifluoro-methanesulfonic acid 2-oxo-4-phenyl-2H-chromen-3-yl ester 
• 113488-03-2 2-cyano-1-methyl-4-phenyl-1-selenanaphthalene 
• 17831-88-8 4-chloro-2H-1-benzopyran-2-one 
• 98-80-6 phenylboronic acid 
• 113777-29-0 4-(trifluoromethylsulfonyloxy)coumarin 
• 91-64-5 coumarin 
• 587-85-9 diphenylmercury(II) 
• 637-44-5 phenylpropyolic acid 

Downstream Products

• 121507-65-1 2,2,4-Triphenyl-2H-benzopyran 
• 29909-72-6 3-Phenylbenzofuran 
• 1379805-13-6 3-(2-hydroxyphenyl)-3-phenylacrylic acid 
• 1562426-68-9 4-phenyl-3-(trifluoromethyl)-2H-1-benzopyran-2-one 

Relevant academic research and scientific papers

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

Transition-Metal-Free Lactonization of sp2 C-H Bonds with CO2

The transition-metal-free lactonization of heteroaryl and alkenyl C-H bonds with carbon dioxide is reported to synthesize important coumarin derivatives in moderate to excellent yields. These redox-neutral reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.

Magnesium bis(trifluoromethane)sulfonimide: An efficient catalyst for the synthesis of coumarins under solvent-free conditions

Magnesium bis(trifluoromethane)sulfonimide [Mg(NTf2) 2] is an efficient catalyst for the synthesis of coumarins via the Pechmann condensation reaction of phenols and β-ketoesters under solvent-free conditions.

Visible-Light-Induced Direct Csp2-H Radical Trifluoroethylation of Coumarins with 1,1,1-Trifluoro-2-iodoethane (CF3CH2I)

Herein, we developed the first visible-light-induced direct Csp2-H radical 2,2,2-trifluoroethylation of coumarins with commercially available and cheap reagent CF3CH2I at room temperature. This transformation proceeded smoothly under mild conditions and showed excellent functional group compatibility. The synthetic value of the protocol was also demonstrated by the successful functionalization of several pharmaceuticals.

Chlorinative Cyclization of Aryl Alkynoates Using NCS and 9-Mesityl-10-methylacridinium Perchlorate Photocatalyst

In a chlorinative cyclization, Mes-Acr-MeClO4 acted as a visible-light photocatalyst to obtain 3-chlorocoumarins from aryl alkynoates and N-chlorosuccinimide (NCS). The radical initiated reaction proceeded in a cascading manner via Cl- addition to alkynoa

Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons

Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.

An evaluation of palladium-based catalysts for the base-free borylation of alkenyl carboxylates

Synthesis of organoboron derivatives is a key application of catalytic cross-coupling, with the Pd-catalyzed Miyaura borylation among the most versatile methods available. We have evaluated several Pd-based systems for borylation of alkenyl acetates and p

Fe-Catalyzed Intramolecular Cross-Dehydrogenative Arylation (CDA), Efficient Synthesis of 1-Arylnaphthalenes and 4-Arylcoumarins

Direct cross-dehydrogenative coupling of different inert C?H bonds is the most straightforward and environmentally benign method to construct C?C bonds. In this paper, we developed an iron-catalyzed intramolecular cross-dehydrogenative arylation (CDA) between benzylic C(sp3)H bond and aromatic C(sp2)H bond. From the readily available linear substrates, 1-arylnaphthalenes and 4-arylcoumarins can be quickly constructed with moderate to good yield (18 examples, up to 73 % yield) in one step. Both symmetrical and unsymmetrical substrates with different functional groups could tolerate this system well to form the anticipated products. A radical initiated dehydrogenative cyclization-dehydrogenation tandem process was proposed.

Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst

We have developed an efficient photocatalytic synthesis of coumarin derivativesviaa tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives dimerized lignan-type products.

Nickel-Catalyzed Decarbonyloxidation of 3-Aryl Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones

We have developed a protocol to facilitate the nickel-catalyzed decarbonyloxidation of 3-aryl benzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions, which is an efficient approach for the decarbonyloxidation of lactones in organic synthesis. A diverse range of substrates can undergo C(O)-O/C(O)-C bond cleavage to generate the target products in good yields. These 2-hydroxybenzophenones can be converted into a variety of compounds via reactions such as esterification, cyclization, and reduction.