66021-96-3

Upstream product

• 211696-94-5 2-(trimethylsilylethynyl)-(2-propenyloxy)benzene 
• 533-58-4 2-Iodophenol 
• 90-02-8 salicylaldehyde 
• 28752-82-1 2-(allyloxy)benzaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 81787-62-4 o-((trimethylsilyl)ethynyl)phenol 
• 102851-74-1 1-(allyloxy)-2-(2,2-dibromovinyl)benzene 

Downstream Products

• 211696-98-9 1-Allyloxy-2-pent-4-en-1-ynyl-benzene 
• 374547-66-7 2-(phenylethynyl)-(2-propenyloxy)benzene 
• 102851-75-2 methyl 3-<2-(2-propenyloxy)phenyl>prop-2-ynoate 
• 211696-95-6 1-(allyloxy)-2-(prop-1-yn-1-yl)benzene 
• 102851-80-9 (Z)-4-(2-Allyloxy-phenyl)-4-(hydroxy-methyl-amino)-but-3-en-2-one 
• 102851-79-6 C,N-dimethyl-C-(2-(2-propenyloxy)phenylethynyl)nitrone 
• 102851-77-4 4-<2-(2-propenyloxy)phenyl>but-3-yn-2-one 
• 102851-76-3 4-<2-(2-propenyloxy)phenyl>but-3-yn-2-ol 

Relevant academic research and scientific papers

Catalytic Generation of Rhodium Silylenoid for Alkene-Alkyne-Silylene [2 + 2 + 1] Cycloaddition

An alkene-alkyne-silylene [2 + 2 + 1] cycloaddition takes place in the rhodium-catalyzed reaction of 1,6-enynes with borylsilanes bearing an alkoxy group on the silicon atoms, which react as synthetic equivalents of silylene. The reaction proceeds efficiently in 1,2-dichloroethane at 80-110 °C in the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM) as a ligand to afford 1-silacyclopent-2-enes in good to high yields.

Functionalized Benzofurans via Microwave-Promoted Tandem Claisen-Rearrangement/5-endo-dig Cyclization

Ortho-allyloxy alkinyl benzenes undergo, upon microwave irradiation in dimethylformamide, a tandem sequence of Claisen-rearrangement and 5-endo-dig cyclization to furnish 7-allyl-substituted benzofurans. With terminal alkynes, chroman-4-ones and enaminoketones become the main products. A mechanistic proposal for this observation relies on a reaction of the starting material with the solvent dimethylformamide under the microwave conditions.

Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates

Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.

Silaborative Carbocyclizations of 1,7-Enynes. Diastereoselective Preparation of Chromane Derivatives

Palladium(0)-catalyzed carbocyclization of 1,7-enynes mediated by (chlorodimethylsilyl)pinacolborane proceeds with 1,8-addition of the silicon and boron functions to give functionalized cyclohexane derivatives with boron attached to the exocyclic olefin. A variety of chromane dervatives are accessible by this method. In contrast to the analogous reactions with 1,6-enynes, the configuration of the newly formed stereogenic center is controlled by a stereogenic center present in the substrate.

Gold-catalyzed rearrangement of allylic oxonium ylides: Efficient synthesis of highly functionalized dihydrofuran-3-ones

"Diazo" not needed: The title reaction results in the rearrangement of oxonium ylides, which were prepared from readily available homopropargylic allylic ethers instead of diazo compounds, through two different mechanisms: a concerted 2,3-sigmatropic rearrangement, or a stepwise 1,4-allyl migration followed by a Claisen rearrangement (see scheme). Copyright

Tandem Enyne Metathesis-Diels-Alder Reaction for Construction of Natural Product Frameworks

Enynes connected through aromatic rings are used as substrates for metathesis reactions. The reactivity of three ruthenium carbene complexes is compared. The resulting 1,3-dienes are suitable precursors of polycyclic structures via a Diels-Alder process.

Synthesis of bridged medium-sized rings through the intramolecular Pauson-Khand reaction

(Equation presented) A series of aromatic enynes containing steric buttressing elements were prepared and evaluated in the NMO-mediated Pauson-Khand cyclization. O-Allyl systems led to the expected angularly fused products, whereas the O-butenyl and O-pentenyl derivatives afforded the unprecedented bridge systems.

Intramolecular Pauson-Khand reactions of aromatic enynes

The synthesis of a series of O-alkenylated ethynylphenol derivatives and their NMO promoted intramolecular Pauson-Khand reactions are reported. The effects of substitution on both the alkene and alkyne moiety have been investigated.

Palladium-catalyzed allylating heteroannulation of o-alkynyl-allyloxybenzenes. A route to 2-substituted-3-allylbenzo[b]furans

In the presence of palladium(0), o-alkynyl allyloxybenzenes produce 2-substituted 3-allylbenzo[b]furans in fair yields. This heteroannulation is promoted by the η3-allyl palladium species issued from early reaction of the catalyst with the starting allyl aryl ether.

1,3-Dipolar Cycloadditions of Nitrones Derived from the Reaction of Acetylenes with Hydroxylamines

A study of the reaction of hydroxylamines with a variety of acetylenes has been carried out.Methylhydroxylamine readily reacts with methyl propiolate to give methyl 4-carbomethoxy-2-methyl-4-isoxazolidine-3-acetate.Further heating of this material results