90535-80-1

Upstream product

• 106-44-5 p-cresol 
• 74-86-2 acetylene 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 35368-57-1 4-methylphenoxyacetamide 
• 7486-35-3 tri-n-butyl(vinyl)tin 

Downstream Products

• 1295507-48-0 2-(1-(1H-indol-3-yl)ethyl)-4-methylphenol 
• 1392836-23-5 2-((2S,4S)-1,2,3,4-tetrahydro-6-methoxy-2-(4-nitrophenyl)-quinolin-4-yl)-4-methylphenol 
• 1447952-04-6 C₂₆H₂₄O₄ 
• 92-48-8 6-methylcoumarin 

Relevant academic research and scientific papers

Bichromatic Photosynthesis of Coumarins by UV Filter-Enabled Olefin Metathesis

Herein, we report on a two-step bichromatic synthesis of coumarins involving UV-A and UV-C light. The first step is a UV-A-photoinduced ruthenium-catalyzed cross-metathesis (CM) reaction of 2-nitrobenzyl-protected 2-hydroxystyrenes with acrylates, using an external solution of 1-pyrenecarboxaldehyde as a UV filter. Irradiation in the absence of the filter permanently inhibits the light-activated catalyst due to photocleavage of the photolabile protecting group (PPG) and ensuing phenolate chelation to the ruthenium. The simple removal of the external filter after CM allows further photochemical reactions with UV-C light to achieve more complex architectures, such as the coumarins presented in this work. (Figure presented.).

Lewis Acid Catalyzed Cyclization of Propargylic Alcohols with 2-Vinylphenol

An unprecedented Lewis acid catalyzed, protection-free, and high-efficiency synthesis of valuable 3,4-dihydro-2H-2,4-methanochromans via cycloaddition of propargylic alkynols with 2-vinylphenol is described. This cycloaddition protocol, which tolerates a

Rh-catalyzed oxidizing group-directed ortho C-H vinylation of arenes by vinylstannanes

An efficient method for the synthesis of functionalized vinyl arenes from the reaction of N-methoxybenzamides or N-phenoxyacetamides with vinylstannanes via rhodium(III)-catalyzed C-H activation is described. The application of the methodology for the synthesis of a natural product thalactamine and a 7-membered ring oxepine are also demonstrated.

Aryloxybenzylidene ruthenium chelates: Synthesis, structure and catalytic activity in olefin metathesis

New aryloxybenzylidene ruthenium chelates behave like a promising latent catalyst of olefin metathesis. The catalysts are characterised by substantial stability and catalytic inactivity in their dormant forms and a dramatic increase in activity after addi

Aryloxybenzylidene ruthenium chelates: Synthesis, structure and catalytic activity in olefin metathesis

New aryloxybenzylidene ruthenium chelates behave like a promising latent catalyst of olefin metathesis. The catalysts are characterised by substantial stability and catalytic inactivity in their dormant forms and a dramatic increase in activity after addi

Straightforward assembly of benzoxepines by means of a rhodium(III)- catalyzed C-H functionalization of o-vinylphenols

Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2] 2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

Endo-selective pd-catalyzed silyl methyl heck reaction

A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.

Palladium-catalyzed asymmetric intermolecular cyclization

Domino cyclization: Alkylpalladium intermediates in an asymmetric Heck reaction were intercepted by a second alkene to give tricyclic products with high enantioselectivity (see scheme; Boc=tert-butoxycarbonyl). The method was applied to the asymmetric syn

Catalytic asymmetric synthesis of cyclic ethers containing an α-tetrasubstituted stereocenter

'Ether' furan or pyran: The exo-selective cyclization of enantioenriched allenols is accomplished with high chirality transfer using as little as 0.02 mol % of a gold catalyst. The new method is effective in the synthesis of a wide range of enantioenriche

Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics

A hydroheteroarylation reaction of vinyl phenols using an alkyl chloride as the sacrificial hydride source is reported. The method tolerates a wide range of heterocycles as the exogenous nucleophile including indoles and pyrroles. The resulting products are easily processed to biologically relevant scaffolds.