103261-31-0

Upstream product

• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 99865-49-3 4-methoxy-2-ethenyl-1-phenyl acetate 
• 150-76-5 4-methoxy-phenol 
• 74-86-2 acetylene 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 

Downstream Products

• 171924-19-9 2-tert-butyldimethylsilyloxy-5-methoxystyrene 
• 99865-49-3 4-methoxy-2-ethenyl-1-phenyl acetate 
• 299465-76-2 1-(1-Benzyloxy-allyloxy)-4-methoxy-2-vinyl-benzene 
• 1295507-49-1 2-(1-(1H-indol-3-yl)ethyl)-4-methoxyphenol 
• 1620026-76-7 C₂₅H₂₆O₄ 
• 1620026-77-8 C₂₅H₂₆O₄ 
• 1620026-58-5 C₂₄H₂₄O₃ 
• 1620026-59-6 C₂₄H₂₄O₃ 
• 1613485-41-8 tert-butyl {3-[2-(2-hydroxy-5-methoxyphenyl)-2-methoxyethyl]-4-methoxyphenyl}carbamate 

Relevant academic research and scientific papers

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

2,6-Divinylation of phenols with ethyne

Phenols are 2,6-divinylated by treatment with ethyne at 100°C in chlorobenzene in the presence of SnCl4-Bu3N, the divinylation occurring predominantly to exclusively with phenol, alkylphenols and alkoxyphenols; an appropriate amount of the tin reagent and the correct reaction temperature are essential for the divinylation.

Synthesis of Benzofuranones via Palladium-Catalyzed Intramolecular Alkoxycarbonylation of Alkenylphenols

Herein, a new catalytic system to synthesize benzofuranones is reported. A palladium-catalyzed intramolecular alkoxycarbonylation is employed to generate 3-substituted-benzofuran-2(3H)-ones from alkenylphenols under mild reaction conditions, linked to an ex situ formation of CO from N-formylsaccharin. The carefully chosen catalytic system enables an efficient reaction with a novel functional group tolerance, despite the high polymerization tendency of the starting material.

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

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.

Substrate-directed hydroacylation: Rhodium-catalyzed coupling of vinylphenols and nonchelating aldehydes

We report a protocol for the hydroacylation of vinylphenols with aryl, alkenyl, and alkyl aldehydes to form branched products with high selectivity. This cross-coupling yields α-aryl ketones that can be cyclized to benzofurans, and it enables access to eu

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.

Ortho-vinylation reaction of phenols with ethyne

Phenols were vinylated at the ortho-position with ethyne in the presence of SnCl4-Bu3N reagent. The reaction was applicable to phenols possessing either electron-donating or electron-withdrawing groups. 2,6-Divinylphenols were synthe

Catalytic asymmetric synthesis of a versatile intermediate for diterpene syntheses. Regioselective olefin insertion in asymmetric Heck reactions

We describe the details of the regioselective asymmetric cyclization of 5 to optically active 8 (95% ee), and the use of this tricyclic compound in the asymmetric synthesis of various diterpenes.