7515-16-4

Upstream product

• 67-56-1 methanol 
• 2227-58-9 3-(4-methylphenyl)prop-2-ynoic acid 
• 148547-94-8 methyl 2,3-dibromo-3-p-tolylpropionic acid methyl ester 
• 66076-78-6 5-p-Tolyl-2,4-dihydro-pyrazol-3-one 
• 124083-42-7 5-p-tolyl-1,2-dihydro-pyrazol-3-one 
• 201230-82-2 carbon monoxide 
• 766-97-2 4-n-methylphenylacetylene 
• 77-78-1 dimethyl sulfate 
• 79-22-1 methyl chloroformate 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 922-67-8 propynoic acid methyl ester 
• 624-31-7 4-tolyl iodide 
• 124-38-9 carbon dioxide 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 

Downstream Products

• 122806-31-9 E-methyl β-piperidino-p-methylcinnamate 
• 122806-30-8 E-methyl β-morpholino-p-methylcinnamate 
• 137201-70-8 E-methyl β-(N,N-diethylamino)-p-methylcinnamate 
• 850635-29-9 methyl (E)-3-(4-methylphenyl)-3-(4-fluorosulfonyl-2,3,5,6-tetramethylphenyl)propenoate 

Relevant academic research and scientific papers

Catalytic tricarbonylation of alkynes with palladium catalysts

A novel catalytic process of introducing three CO units into alkynes by palladium-catalyzed alkoxycarbonylation was developed. Based on the fundamental studies on the behavior of organopalladium complexes, mechanisms to account for the mono- and tricarbon

De Novo Construction of Substituted Terephthalates via Phosphine Catalyzed Domino Benzannulation Reactions

The robustness of phosphine catalysis enabling the domino benzannulation reactions of allenoates with enamines is described. A broad array of substituted terephthalates were delivered under simple and practical reaction conditions. Furthermore, the reaction could be carried out on a gram scale with higher yield, and various conversions of the terephthalate products demonstrate the versatility of this transformation. (Figure presented.).

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

Oxidant- and additive-free simple synthesis of 1,1,2-triiodostyrenes by one-pot decaroboxylative iodination of propiolic acids

A metal- and oxidant-free facile synthesis of a range of 1,1,2-triiodostryrene derivatives has been developed which utilizes a simple decarboxylative triiodination of propiolic acids using molecular iodine and sodium acetate in a one-pot manner. Electron-

Synthesis of 1-Amino-2 H-quinolizin-2-one Scaffolds by Tandem Silver Catalysis

An efficient tandem cycloisomerization-amination reaction catalyzed by silver is described. This rapid and atom-economic reaction delivered 1-amino-2H-quinolizin-2-one scaffolds in high yields under mild conditions. The reaction could be extended to an asymmetric version albeit with moderate enantioselective excess of the products. In addition, the products can be easily reduced into various azabicycles containing 4-pyridones, which are important building blocks in organic synthesis.

Synthetic studies on pyrroloindolizidine skeleton based on gold-catalyzed hydroamination-enamine cyclization-ring-closing metathesis strategy

A pyrroloindolizidine skeleton, which is observed in myrmicarin alkaloids isolated from African ant, is highly unique, oligocyclic indolizidine derivative. We describe here an attempt on a synthesis of a pyrroloindolizidine skeleton with our originally de

Cobalt(III)-Catalyzed Intermolecular Carboamination of Propiolates and Bicyclic Alkenes via Non-Annulative Redox-Neutral Coupling

A cobalt(III)-catalyzed, redox-neutral, intermolecular carboamination of propiolates and bicyclic alkenes was developed. This non-annulative coupling strategy features atom economy, high regioselectivity, good yields, and functional groups tolerance. Such a carboamination reaction was applied to modified phenols from the corresponding phenols under mild conditions.

Transition Metal-Free Trans Hydroboration of Alkynoic Acid Derivatives: Experimental and Theoretical Studies

We report a phosphine-catalyzed trans hydroboration of alkynoate esters and amides. The reaction proceeds under mild conditions with exclusive (E)-selectivity to afford (E)-β-boryl acrylates and (E)-β-boryl acrylamides in good to excellent yields. The reaction is tolerant of a variety of functional groups and allows efficient access to novel oxaboroles as well as a pargyline derivative (MAO inhibitor). Theoretical calculations suggest an internal hydride generates a phosphonium allenoxyborane followed by the formation of a key phosphonocyclobutene intermediate that collapses in a stereoselective, rate-limiting step.

Trans -Hydroboration vs. 1,2-reduction: Divergent reactivity of ynones and ynoates in Lewis-base-catalyzed reactions with pinacolborane

Ynones and ynoates react with pinacolborane in a divergent manner in the presence of nucleophilic phosphine catalysts. Ynones are transformed to the corresponding propargyl alcohols in good yields with high regio- and chemoselectivity. Ynoates undergo highly regio- and stereoselective trans-hydroboration to produce E-vinylboronates. Impressive divergence in reactivity of ynones and ynoates can be traced back to the mechanistic aspects of 1,2-reduction and trans-hydroboration. A comparative analysis of the two pathways paints a complex picture in which different reaction rates control selectivity in these seemingly unrelated processes and explains how sufficiently acidic protons in the reaction mixtures can be used to steer the selectivity in different directions.