30780-51-9

Upstream product

• 138102-18-8 3-(5-Oxo-3-phenyl-4,5-dihydro-isoxazol-4-yl)-propionic acid methyl ester 
• 67-56-1 methanol 
• 30625-91-3 (E)-5-phenylpent-2-en-4-ynal 
• 292638-85-8 acrylic acid methyl ester 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 100-52-7 benzaldehyde 
• 78-94-4 methyl vinyl ketone 
• 536-74-3 phenylacetylene 
• 4312-99-6 oct-1-en-3-one 
• 3350-92-3 5-phenylpent-4-ynoic acid 
• 74-88-4 methyl iodide 
• 52843-77-3 phenylethynyl trifluoromethyl sulfone 
• 591-50-4 iodobenzene 
• 6089-09-4 4-pentynoic acid 

Downstream Products

• 23542-39-4 dimethyl oct-4-ynedioate 
• 501-65-5 diphenyl acetylene 
• 33599-84-7 methyl (E)-5-phenyl-4-pentenoate 
• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 1435517-90-0 3-(4-chlorophenyl)-2,4a-dihydro-1H-fluoren-4-yl benzoate 
• 1435517-82-0 6-bromo-3-phenyl-2,4a-dihydro-1H-fluoren-4-yl benzoate 
• 1435518-59-4 3-cyclopropyl-7-phenylhepta-1,6-diyn-3-yl benzoate 
• 1435518-58-3 3-(naphthalen-1-yl)-7-phenylhepta-1,6-diyn-3-yl benzoate 
• 1435518-57-2 7-phenyl-3-(4-vinylphenyl)hepta-1,6-diyn-3-yl benzoate 
• 1435518-56-1 3-(4-chlorophenyl)-7-phenylhepta-1,6-diyn-3-yl benzoate 
• 1435518-41-4 tert-butyl (3,7-diphenylhepta-1,6-diyn-3-yl)carbonate 
• 1435518-40-3 benzyl (3,7-diphenylhepta-1,6-diyn-3-yl)carbonate 
• 1435518-39-0 3,7-diphenylhepta-1,6-diyn-3-yl acetate 
• 1435518-38-9 3,7-diphenylhepta-1,6-diyn-3-yl benzoate 

Relevant academic research and scientific papers

A NEW PRACTICAL METHOD FOR THE SYNTHESIS OF ACETYLENES

The reaction of isoxazol-5-ones derived from β-keto esters and hydroxylamine with sodium nitrite and ferrous sulphate in aqueous acetic acid affords the corresponding acetylenes in moderate to good yield. Key Words: Alkynes; Isoxazol-5-ones; β-Keto esters

A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation

Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom-economic reducing agent dihydrogen (H2), only few catalysts for the challenging E-selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E-selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E-alkenes employing H2, which could serve as a general method for synthesis.

Gold-catalyzed Rapid Construction of Nitrogen-containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

1,3-unsubstituted 2-(1H-indol-2-yl)ethanamines were employed for the first time to react with alkynoic acids (AAs) to achieve gold-catalyzed highly selective cascade reactions to furnish novel indole-fused skeletons. Furthermore, with this powerful gold catalytic system, a library of indole/pyrrole/thiophene/benzene/naphthalene/pyridine-based nitrogen-containing heterocyclic compounds (NCHCs) with scaffold diversity and molecular complexity was constructed rapidly using various amine nucleophiles (ANs) and diverse AAs as the building blocks. This general protocol features excellent selectivity, extraordinarily broad substrate scope, readily available inputs, good to high yields, high bond-forming efficiency, and step economy, thus providing a facile and efficient access to a variety of valuable nitrogen-containing heterocycles.

Diversity-Oriented Desulfonylative Functionalization of Alkyl Allyl Sulfones

The diversity-oriented desulfonylative functionalization of alkyl allyl sulfones with various sulfone-type reagents by radical chemistry has been developed. The readily installed allylsulfonyl moiety acts as a C-radical precursor, which is substituted by various functionalities using sulfur-based radical trapping reagents. The generality of this approach is documented by the successful desulfonylative alkynylation, azidation, trifluoromethylthiolation, sulfenylation, trifluoromethylselenylation, halogenation, and deuteration. The method is compatible with a wide range of functional groups. Considering the deuteration, products are obtained in good yields with a high level of deuterium incorporation.

Asymmetric Three-Component Coupling Reaction of Alkyne, Enone, and Aldehyde Catalyzed by Chiral Phebox Ruthenium Catalysts

Catalytic asymmetric three-component coupling reactions of terminal alkynes, α,β-unsaturated ketones, and aldehydes were studied. The chiral ruthenium complexes containing bis(oxazolinyl)phenyl ligands were found to serve as efficient catalysts for a tandem reaction based on conjugate addition of terminal alkynes to α,β-unsaturated ketones and subsequent aldol reaction with aldehydes, giving β-hydroxyketone derivatives containing α-propargyl groups in high yields with moderate to good enantioselectivities. This method can produce various functional molecules from commercially available substrates in a one-pot procedure. The absolute configuration of the major product was determined by X-ray analysis. The control experiments suggested that a ruthenium enolate species generated in situ by conjugate addition could be involved as an intermediate for the aldol coupling with an aldehyde.

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

Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1 H-fluorenes

A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM′) [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics:quantum mechanics′)] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.

Indium(III) chloride catalyzed conjugate addition reaction of alkynylsilanes to acrylate esters

A novel and efficient procedure for the synthesis of δ,γ- alkynyl esters by the conjugate addition of alkynylsilanes to acrylate esters in the presence of a catalytic amount of indium(III) chloride has been developed. This method provides a rapid and efficient access to substituted δ,γ-alkynyl esters.

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.

Ruthenium/halide catalytic system for C-C bond forming reaction between alkynes and unsaturated carbonyl compounds

A ruthenium complex [triruthenium dodecacarbonyl, Ru3(CO) 12] in the presence of bis(triphenylphosphine)iminium chloride ([PPN]Cl) catalyzes the conjugate addition of terminal alkynes to alkyl acrylates to give high yields of γ,δ-alkynyl esters. On the other hand, the linear codimerization reaction of terminal alkynes with alkyl acrylates proceeds in the presence of a catalytic amount of Ru 3(CO)12 and lithium iodide to give the corresponding conjugate dienes. These two different types of catalytic carbon-carbon bond forming reactions are controlled only by the nature of halide ions, either a chloride or an iodide, with other conditions being kept almost the same.