62248-76-4

Upstream product

• 78-94-4 methyl vinyl ketone 
• 536-74-3 phenylacetylene 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 459126-04-6 diethyl (3-phenylprop-2-yn-1-yl) phosphate 
• 75-16-1 methylmagnesium bromide 
• 3350-92-3 5-phenylpent-4-ynoic acid 
• 591-50-4 iodobenzene 
• 2550-28-9 5-hexyn-2-one 
• 73513-15-2 (3-iodo-1-propyn-1-yl)benzene 
• 557773-94-1 1-phenyl-2-(triphenylphosphoranylidene)hexane-1,5-dione 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 

Downstream Products

• 6303-82-8 1-phenylhexane-1,5-dione 
• 32776-14-0 1-phenyl-hexane-2,5-dione 
• 131529-75-4 N-allyl-1-methyl-5-phenyl-4-pentynylamine 
• 1590431-50-7 6-methyl-2-phenylbicyclo[4.2.0]octa-1,3-diene 
• 51010-53-8 1-benzyl-4-methylnaphthalene 

Relevant academic research and scientific papers

Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones

The metal complex Rh(acac)(CO)2 in the presence of an eqimolar amount of tris(o-methoxyphenyl)phosphine provides a useful catalyst system for the 1,4-addition of alkynes to unsubstituted vinyl ketones. Best yields are obtained when the transfor

The first palladium-catalyzed 1,4-addition of terminal alkynes to conjugated enones

The first palladium-catalyzed 1,4-addition of terminal alkynes to conjugated enones has been developed in water and in acetone, producing the corresponding γ,δ-alkynyl ketones in high yields.

Enantioselective Nickel-Catalyzed anti-Arylmetallative Cyclizations onto Acyclic Ketones

Domino reactions involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization of the alkenylnickel intermediates onto tethered acyclic ketones to give chiral tertiary-alcohol-containing products in high enantioselectivities, are described. The reversible E/Z isomerization of the alkenylnickel intermediates enables overall anti-arylmetallative cyclization to occur. The ring system of the products are substructures of certain diarylindolizidine alkaloids.

K2CO3-Mediated Cyclization and Rearrangement of γ,δ-Alkynyl Oximes to Form Pyridols

A novel K2CO3-mediated cyclization and rearrangement of γ,δ-alkynyl oximes for the synthesis of pyridols is described. The process accomplishes an efficient [1,3] rearrangement of the O-vinyl oxime intermediate which is in situ generated from the intramolecular nucleophilic addition of γ,δ-alkynyl oximes. The reaction employs readily accessible starting materials, tolerates a wide range of functional groups, and gives a variety of synthetically challenging pyridols in good yields.

Gold-catalyzed enantioselective ring-expanding cycloisomerization of cyclopropylidene bearing 1,5-enynes

An enantioselective ring-expanding cycloisomerization of 1,5-enynes bearing a cyclopropylidene moiety has been developed. This methodology provides a new approach to bicyclo[4.2.0]octanes, a structural motif present in many biologically active natural products.

Direct conjugate addition of alkynes with α,β-unsaturated carbonyl compounds catalyzed by NCN-pincer Ru complexes

NCN-pincer Ru-complexes containing bis(oxazolinyl)phenyl ligands serve as suitable catalysts in the direct conjugate additions of α,β- unsaturated carbonyl compounds, including ketones, esters, and amides, as well as vinylphosphonates, giving various β-alkynyl carbonyl and phosphonate compounds. A bis(oxazolinyl)phenyl (phebox)-Ru complex also catalyzes the asymmetric conjugate addition of an alkyne with a β-substituted, α,β-unsaturated ketone to produce a chiral β-alkynyl ketone. Copyright

Ruthenium-catalyzed three-component coupling via hydrative conjugate addition of alkynes to alkenes: One-pot synthesis of 1,4-dicarbonyl compounds

A catalytic three-way rendezvous: Terminal alkynes undergo metal vinylidene formation, anti-Markovnikov hydration to give a metal acyl complex, and conjugate addition to produce synthetically useful 1,4-dicarbonyl compounds under ruthenium catalysis. This one-pot three-component coupling reaction is a useful platform for further exploration in alkyne functionalization.

1, 4-addition of terminal alkynes to conjugated enones in water using green catalyst bis[(l)prolinato-N,O]Zn-An environmentally benign protocol

An easy, low cost, and green procedure is proposed for the 1, 4-addition of terminal alkynes to conjugated enones in water as a sole medium using easily accessible Zn[(l)Proline]2. This protocol has advantages of high yield, mild reaction condi

A homogeneous, recyclable polymer support for rh(I)-catalyzed c-c bond formation

A robust and practical polymer-supported, homogeneous, recyclable biphephos rhodium(I) catalyst has been developed for C-C bond formation reactions. Control of polymer molecular weight allowed tuning of the polymer solubility such that the polymer-supported catalyst is soluble in nonpolar solvents and insoluble in polar solvents. Using the supported rhodium catalysts, addition of aryl and vinylboronic acids to the electrophiles such as enones, aldehydes, N-sulfonyl aldimines, and alkynes occurs smoothly to provide products in high yields. Additions of terminal alkynes to enones and industrially relevant hydroformylation reactions have also been successfully carried out. Studies show that the leaching of Rh from the polymer support is low and catalyst recycle can be achieved by simple precipitation and filtration.

Palladium-catalyzed 1,4-addition of terminal alkynes to unsaturated carbonyl compounds promoted by electron-rich ligands

The efficient palladium-catalyzed conjugate addition of terminal alkynes to α,β-unsaturated carbonyl compounds has been developed using electron-rich ligands, producing the corresponding γ,δ-alkynyl ketone and γ,δ-alkynyl esters in good yields. The Royal Society of Chemistry.