7517-82-0

Upstream product

• 16419-60-6 2-Methylphenylboronic acid 
• 922-67-8 propynoic acid methyl ester 
• 615-37-2 ortho-methylphenyl iodide 
• 124-38-9 carbon dioxide 
• 3989-15-9 trimethyl[(2-methylphenyl)ethynyl]silane 
• 74-88-4 methyl iodide 
• 147501-26-6 methyl 3-oxo-3-(o-tolyl) propanoate 
• 79-22-1 methyl chloroformate 
• 766-47-2 1-ethynyl-2-methylbenzene 
• 186581-53-3 diazomethane 
• 7515-27-7 3-(2-methylphenyl)prop-2-ynoic acid 
• 95-53-4 o-toluidine 

Downstream Products

• 75950-75-3 3-(2'-methylphenyl)-(Z)-propenoic acid methyl ester 

Relevant academic research and scientific papers

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.

Organocatalytic trans Phosphinoboration of Internal Alkynes

We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P-Bpin are efficiently converted into the corresponding trans-α-phosphino-β-boryl acrylate products in moderate to good yield with high regio- and Z-selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only a modest excess of the phosphinoboronate. X-ray crystallography experiments allowed structural assignment of the unprecedented and densely functionalized (Z)-α-phosphino-β-boryl acrylate products.

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-

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.

Rhodium(III)-Catalyzed Redox-Neutral Cascade [3 + 2] Annulation of N-Phenoxyacetamides with Propiolates via C-H Functionalization/Isomerization/Lactonization

A Rh(III)-catalyzed cascade [3 + 2] annulation of N-phenoxyacetamides with propiolates under mild conditions using the internal oxidative O-N bond as the directing group has been achieved. This catalytic system provides a regio- and stereoselective access to benzofuran-2(3H)-ones bearing exocyclic enamino motifs with exclusive Z configuration selectivity, acceptable to good yields and good functional group compatibility. Mechanistic investigations by experimental and density functional theory studies suggest that a consecutive process of C-H functionalization/isomerization/lactonization is likely to be involved in the reaction.

Salt-Free Strategy for the Insertion of CO2 into C?H Bonds: Catalytic Hydroxymethylation of Alkynes

A copper(I) catalyst enables the insertion of carbon dioxide into alkyne C?H bonds by using a suitable organic base with which hydrogenation of the resulting carboxylate salt with regeneration of the base becomes thermodynamically feasible. In the presence of catalytic copper(I) chloride/4,7-diphenyl-1,10-phenanthroline, polymer-bound triphenylphosphine, and 2,2,6,6-tetramethylpiperidine as the base, terminal alkynes undergo carboxylation at 15 bar CO2 and room temperature. After filtration, the ammonium alkynecarboxylate can be hydrogenated to the primary alcohol and water at a rhodium/molybdenum catalyst, regenerating the amine base. This demonstrates the feasibility of a salt-free overall process, in which carbon dioxide serves as a C1 building block in a C?H functionalization.

Palladium-Catalyzed Synthesis of Conjugated Allenynes via Decarboxylative Coupling

A new strategy to access conjugated allenynes via a decarboxylative coupling of propargyl esters of propiolates has been developed. In this process, allenyl-palladium intermediates are coupled with acetylides that are generated in situ to form the conjuga

One-pot synthesis of propynoates and propynenitriles

An efficient transformation towards propynoates and propynenitriles is herein described. The practical methodology was conducted at low temperature (-78 or -60 °C) in a one-pot manner with the assistance of base rather than any transition metal catalysts. The base-induced protocol exhibits good functional group tolerance (up to 28 examples) and high efficiency (up to 92% yields) towards substituted acetylenes of great synthetic significance, which was also well demonstrated by the gram-scale reactions.

Novel methoxy acrylate compound, as well as preparation method and application thereof

The invention provides a novel methoxy acrylate compound, as well as a preparation method and application thereof, and relates to the technical field of pesticide sterilization. The novel methoxy acrylate compound has novel structure and broad-spectrum sterilization activity at the same time, even a small amount of the novel methoxy acrylate compound can achieve a remarkable effect, and the novel methoxy acrylate compound can be used for preparing a novel bactericide for preventing and controlling diseases of crops. The preparation method for the novel methoxy acrylate compound is simple, mild in condition and easy to operate, and a bactericidal substance with a good bactericidal effect can be prepared. The novel methoxy acrylate compound has higher bactericidal activity, and can be applied to the field of bactericides.

Copper-catalyzed, aerobic oxidative cross-coupling of alkynes with arylboronic acids: Remarkable selectivity in 2,6-lutidine media

Aerobic oxidative cross-coupling reactions between alkynes and boronic acids under mild conditions catalyzed by low loadings of a copper salt are reported. 2,6-Lutidine accelerated the reactions dramatically, and the desired coupling products were obtained in high yields with high selectivities.