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Upstream product

• 1612-03-9 3-methyl-1-phenyl-but-1-yne 
• 591-50-4 iodobenzene 
• 598-23-2 3-methyl-but-1-yne 
• 2978-58-7 1,1-dimethylprop-3-ynylamine 

Downstream Products

• 1389334-42-2 1,5-dihydro-4-hydroxy-5,5-dimethyl-3-phenyl-2H-pyrrol-2-one 

Relevant academic research and scientific papers

Efficient and Reusable Metal–Organic Framework Catalysts for Carboxylative Cyclization of Propargylamines with Carbon Dioxide

Carbon dioxide (CO2) capture and transformation are important for decreasing the concentration of atmospheric CO2. To effectively capture CO2 and further fix it into valuable chemical products, functionalized dynamic metal–organic frameworks (MOFs) have been utilized not only because of their inherent cavity for accommodating CO2 but also owing to their reversible structural transformations in response to external stimuli for regulating the reaction. Herein, we report a dynamic and functional MOF [Cd3(L)2(BDC)3]2?16 DMF (MOF-1 a; DMF=N,N-dimethylformamide) achieved by reaction of the amino tripodal imidazole ligand N1-(4-(1 H-imidazol-1-yl)benzyl)-N1- (2-aminoethyl)ethane-1,2-diamine (L) and 1,4-benzenedicarboxylic acid (H2BDC) with cadmium salt. MOF-1 a not only shows unprecedented high catalytic activity [initial turnover number (TON) up to 9300] and broad substrate scope for the carboxylative cyclization of propargylamines with CO2, but also can be switched on and off upon reversible structural transformation owing to its dynamic five-fold interpenetrating structure. Further studies demonstrate that MOF-1 a shows selective catalytic properties depending on the size of substrates, similarly to sophisticated biological systems.

Palladium-Catalyzed Carbonylative Synthesis of 1,5-Dihydro-2H-pyrrol-2-ones from Propargyl Amines and Benzyl Chlorides

A palladium-catalyzed double carbonylation of propargyl amines and benzyl chlorides employing benzene-1,3,5-triyl triformate (TFBen) as the CO source has been developed. By using this protocol, various 1,5-dihydro-2H-pyrrol-2-ones were produced in good yields. (Figure presented.).

An Enzymatic Platform for Primary Amination of 1-Aryl-2-alkyl Alkynes

Propargyl amines are versatile synthetic intermediates with numerous applications in the pharmaceutical industry. An attractive strategy for efficient preparation of these compounds is nitrene propargylic C(sp3)-H insertion. However, achieving this reacti

Benzene-1,3,5-triyl Triformate (TFBen)-Promoted Palladium-Catalyzed Carbonylative Synthesis of 2-Oxo-2,5-dihydropyrroles from Propargyl Amines

In this letter, we developed a palladium-catalyzed procedure for the cyclocarbonylation of propargyl amines. Benzene-1,3,5-triyl triformate (TFBen) has been explored as the CO source and also as the key promotor. Various substituted 2-oxo-dihydropyrroles were produced in a facile manner in good yields (up to 90%).

Stereoselective amination: Via vinyl-silver intermediates derived from silver-catalyzed carboxylative cyclization of propargylamine

The stereoselective synthesis of aminovinyloxazolidinones based on the electrophilic amination of a vinyl-silver intermediate, generated by silver-catalyzed carbon dioxide incorporation on a propargyl amine, was achieved. The geometry of the aminated product was determined by a single crystal X-ray analysis and NOE measurement and it was elucidated that the geometry was proved to be opposite to the geometry predicted from the previous silver-catalyzed carbon dioxide fixation on a propargyl amine derivative. This unexpected stereoselectivity could be successfully explained by a radical mechanism. This journal is

Synthesis of Halogenated Cyclic Enamines from Cyclic N-2-En-4-ynyl-N-1-ynylamides and N-Propargyl-N-1-ynylamides via a Tandem Iron Halide Promoted N-to-C Shift-Aza-Prins Cyclization Sequence

A facile and efficient N-to-C allyl shift-aza-Prins cyclization sequence of cyclic N-2-en-4-ynyl-N-1-ynylamides is promoted by iron(III) chloride, generating chloro-containing bridged bicyclic enamines in minutes and in high yields. This reaction involves an unprecedented formation of a ketenimine via Fe(III)-mediated N-to-C allyl rearrangement, followed by aza-Prins cyclization. This sequence can also be applied to the generation of brominated cyclobutenamine derivatives using Fe(III) bromide and N-propargyl-N-1-ynylamides. (Figure presented.).

Base-Promoted Sulfur-Mediated Carbonylative Cyclization of Propargylic Amines

A tBuOK-mediated carbonylative cyclization of propargylic amines with elemental sulfur has been developed. With benzene-1,3,5-triyl triformate (TFBen) as a convenient CO surrogate, various substituted 1,3-thiazolidin-2-ones were produced in good to excellent yields.

Silver-Catalyzed Cyclization of Propargylic Amides to Oxazolines

A ligand-accelerated effect is observed in the cyclization of propargylic amides catalyzed by bis(pyridyl)silver(I) complexes, with an unexpected reversal of electronic demand to the analogous NH addition reaction. The catalyst was found to be effective for internal alkyne substrates, offering exclusive selectivity for the 5-exo-dig product. Differences in selectivity profile between gold- and silver-catalyzed processes are highlighted and discussed.

Silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for stereoselective preparation of (E)-iodovinyloxazolidinones

The silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for the stereoselective synthesis of (E)-iodovinyloxazolidinones was developed. The silver-catalytic system could be applied to various propargylic amines to afford the corresponding iodovinyloxazolidinones in high yields. The structure of the oxazolidinone was confirmed by X-ray structure analysis to be the Eisomer for the geometry of the exo-olefin. The silver-catalyzed cyclization and replacement of silver with the iodine group in the intermediate were thought to be crucial steps.

Novel method of tetramic acid synthesis: Silver-catalyzed carbon dioxide incorporation into propargylic amine and intramolecular rearrangement

Tetramic acid derivatives have been studied as biologically active heterocycle structures for pharmaceutical or agricultural chemicals. Conventional preparative approaches often require highly functionalized starting materials and harsh heating conditions in basic media. The present report provides a conceptually new synthetic strategy for the synthesis of tetramic acid derivatives from easily available propargylic amines and carbon dioxide with a silver salt and DBU under mild reaction conditions.