3350-92-3

Upstream product

• 91368-76-2 (3-phenyl-prop-2-ynyl)-malonic acid 
• 536-74-3 phenylacetylene 
• 49769-22-4 3-(4-phenyl-[1,2,3]selenadiazol-5-yl)-propionic acid 
• 57-57-8 β-Propiolactone 
• 131529-87-8 ethyl 5-phenyl-4-pentynoate 
• 591-50-4 iodobenzene 
• 6089-09-4 4-pentynoic acid 
• 73172-56-2 ethyl 4-benzoylbutanoate 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 2579-22-8 Phenylpropargyl aldehyde 
• 729580-70-5 n-butyl 5-phenyl-4-pentynoate 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 5390-04-5 pent-1-yn-5-ol 
• 21565-82-2 methyl pent-4-ynoate 

Downstream Products

• 4055-00-9 6-phenyl-3,4-dihydropyran-2-one 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 69063-22-5 (Z)-γ-benzylidene-γ-butyrolactone 
• 69063-22-5 (E)-5-benzylidene-γ-butyrolactone 
• 131529-84-5 N-methyl-5-phenyl-pent-4-ynamide 
• 73850-28-9 6-(4-Hydroxy-phenyl)-6-phenyl-dihydro-pyran-2,5-dione 
• 300662-69-5 5-phenyl-4-pentynoic acid chloride 
• 65111-06-0 oct-4-ynedioic acid 
• 501-65-5 diphenyl acetylene 
• 30780-51-9 5-phenylpent-4-ynoic acid methyl ester 
• 864682-09-7 3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 928768-37-0 N-benzyl-5-phenyl-pent-4-ynamide 
• 1186400-11-2 7-(oxiran-2-yl)heptyl 5-phenylpent-4-ynoate 
• 1213759-53-5 C₂₉H₃₆N₄O₂ 

Relevant academic research and scientific papers

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids

Silver complexes with 5-(4-(tert-butyl)-1H-imidazol-1-yl)-imidazo[1,5-a]pyridin-3-ylidene ligands were synthesized as metal-imidazole acid-base cooperative catalysts. Single crystal XRD analysis revealed that the silver atom was located in the vicinity of

Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions

The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.

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.

Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization

A new synthetic approach to thiolactones that employs an efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization to convert unsaturated thiocarboxylic acid derivatives into thiolactones under very mild conditions is described. The high overall yields, fast kinetics, high diastereoselectivity, excellent regiocontrol, and broad substrate scope of these reaction processes render this a very useful approach for diversity-oriented synthesis and drug discovery efforts. A detailed computational rationale is provided for the observed regiocontrol.

Palladium NNC Pincer Complex as an Efficient Catalyst for the Cycloisomerization of Alkynoic Acids

A two-step (nucleophilic substitution/palladation by oxidative addition) sequence provides a high-yielding access to a non-symmetrical palladium NNC pincer complex. A number of terminal and internal alkynoic acids with different substitution patterns at the α- and β-positions are regio- and diastereoselectively cycloisomerized to the corresponding exocyclic enol lactones in the presence of exceedingly low amounts of the latter palladium complex, so that unprecedented turnover numbers and frequencies ranging from 1,000,000 to 700,000 and from 41,667 to 9722 h?1, respectively, are achieved. The optimized protocol, based on the use of a catalytic amount of triethylamine as base, allows an easy real-time monitoring of the reaction by NMR spectroscopy. Several pieces of evidence in favor of the direct participation of the above pincer complex as the catalyst of the reaction have been gathered from kinetic and poisoning experiments. (Figure presented.).

Cycloisomerization of acetylenic acids to γ-alkylidene lactones using a palladium(II) catalyst supported on amino-functionalized siliceous mesocellular foam

Cycloisomerization of various γ-acetylenic acids to their corresponding γ-alkylidene lactones by the use of a heterogeneous Pd(II) catalyst supported on amino-functionalized siliceous mesocellular foam is described. Substrates containing terminal as well

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.

The combination of relay and cooperative catalysis with a gold/palladium/brnsted acid ternary system for the cascade hydroamination/ allylic alkylation reaction

The combination of relay and cooperative catalysis with a gold/palladium/Brnsted acid ternary system renders a cascade hydroamination/allylic alkylation reaction to provide an unprecedented entry to pyrrolidine derivatives in high yields. Copyright

Alkyne-mediated domino hydroformylation/double cyclization: Mechanistic insight and synthesis of (±)-tashiromine

A novel domino reaction, alkyne-mediated domino hydroformylation/double cyclization, has been developed for rapid preparation of indolizidine type alkaloids. DFT calculations were applied for rationales of reactivity and selectivity. A concise synthesis of tashiromine as the application of the methodology is also reported.