211696-94-5

Upstream product

• 81787-62-4 o-((trimethylsilyl)ethynyl)phenol 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 
• 1066-54-2 trimethylsilylacetylene 
• 28752-82-1 2-(allyloxy)benzaldehyde 
• 90-02-8 salicylaldehyde 
• 24892-63-5 1-allyloxy-2-iodobenzene 
• 75-77-4 chloro-trimethyl-silane 
• 102851-74-1 1-(allyloxy)-2-(2,2-dibromovinyl)benzene 
• 533-58-4 2-Iodophenol 

Downstream Products

• 66021-96-3 1-ethynyl-2-(2-propen-1-yloxy)benzene 

Relevant academic research and scientific papers

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.

A novel stereoselective photoinduced intramolecular cyclization of 1- (o-allyloxyphenyl)-2-pentamethyldisilanyl ethynes

Photolysis of 1-(o-allyloxyphenyl)-2-pentamethyldisilanyl ethynes 1a and 1b in benzene provides novel stcreoselective intramolecular cyclization products 3a and 3b.

Cycloisomerization between Aryl Enol Ether and Silylalkynes under Ruthenium Hydride Catalysis: Synthesis of 2,3-Disubstituted Benzofurans

Metal-catalyzed cycloisomerization reactions of 1,n-enynes have become conceptually and chemically attractive processes in the search for atom economy, which is a key subject of current research. However, metal-catalyzed cycloisomerization between aryl enol ether and silylalkynes has not been developed. The ruthenium hydride complex catalyzed cycloisomerization between aryl enol ether and silylalkynes is reported to give benzofurans having useful functional groups, vinyl and trimethylsilylmethyl, on the 2- and 3-positions, respectively.

From ynamides to highly substituted benzo[b]furans: Gold(I)-catalyzed 5-endo-dig-cyclization/rearrangement of alkylic oxonium intermediates

A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross-coupling/amidation sequence. The gold-catalyzed conversion of these substrates combined both C-O and C-C formation steps, thus providing benzofurans with amine functionalities at the 2-position and alkyl groups at the 3-position. Cross-over experiments showed that the alkyl-migration step was an intermolecular process. X-ray crystal-structure analysis of two of the products supported our structural assignment. In some cases, the corresponding benzofurans without the alkyl group at the 3-position were obtained as side-products, which were formed through a competing protodeauration process. Golden touch: Arylynamides with o-alkyloxy groups were prepared through an alkylation/cross-coupling/amidation sequence. Their Au-catalyzed conversion provided benzofurans with amine groups at the 2-position and alkyl groups at the 3-position. 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.

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.