7572-40-9

Upstream product

• 67-56-1 methanol 
• 7396-28-3 3-(3-chlorophenyl)prop-2-ynoic acid 
• 79-22-1 methyl chloroformate 
• 227936-62-1 1-chloro-3-[2-(trimethylsilyl)ethynyl]benzene 
• 7647-01-0 hydrogenchloride 
• 84750-91-4 1-chloro-3-(2,2-difluorovinyl)benzene 
• 625-99-0 3-iodochlorobenzene 
• 766-83-6 m-chlorophenylacetylene 
• 74-88-4 methyl iodide 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 7396-28-3 3-(3-chlorophenyl)prop-2-ynoic acid 

Relevant academic research and scientific papers

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.).

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.

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.

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.

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

Preparation of 1-aryl-2-bromo-3,3-difluorocyclopropenes

1-Aryl-2-bromo-3,3-difluorocyclopropanes were prepared from the reaction of 2′,2′-difluorostyrene and dibromocarbene instead of from 1-aryl-2-haloacetylenes and difluorocarbene. These results are rationalised by the energy gap between HOMO(styrene), HOMO(acetylene) and LUMO(CX2). The title compounds were converted to methyl arylpropynoate in MeOH solution in quantitative yield.

Synthesis of 2-amino-6-phenyl-4H-pyran-4-ones

The treatment of a series of phenylacetylenic β-keto amides with methanesulfonic acid produces a high yielding intramolecular cyclization to the corresponding 2-amino-6-phenyl-4H-pyran-4-ones.