69063-20-3

Upstream product

• 3350-92-3 5-phenylpent-4-ynoic acid 
• 591-50-4 iodobenzene 
• 6089-09-4 4-pentynoic acid 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 5390-04-5 pent-1-yn-5-ol 
• 540803-87-0 6-phenylhex-5-ynoic acid 
• 3183-15-1 4-oxo-5-phenylvaleric acid 

Downstream Products

• 928215-54-7 4-oxo-5-phenylpentanamide 
• 105886-84-8 (Z)-5-Phenylmethylene-pyrrolidin-2-one 
• 105886-76-8 (E)-5-Phenylmethylene-pyrrolidin-2-one 
• 928215-56-9 4-oxo-5-phenylpentan-N-(3-nitrophenyl)amide 
• 928215-58-1 2-benzyl-2-hydroxy-1-methylpyrrrolidin-5-one 
• 42464-63-1 (E)-2-benzylidene-1-methylpyrrolidin-5-one 
• 927898-77-9 1,2-dibenzyl-2-hydroxypyrrolidin-5-one 

Relevant academic research and scientific papers

A mild access to γ- or δ-alkylidene lactones through gold catalysis

ω-Acetylenic acids are efficiently and stereoselectively converted to the corresponding enol lactones in the presence of catalytic amounts of AuCl and K2CO3.

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.

Impregnated palladium on magnetite as a water compatible catalyst for the cycloisomerization of alkynoic acid derivatives

This work describes the catalytic activity of palladium(ii) species in the cycloisomerization of alkynoic acids and their derivatives in aqueous media as well as in Deep Eutectic Solvents (DESs), with one of the lowest metal catalyst loadings reported so far in the literature. Different substrates such as terminal and internal alkynes or alkynyl sulfonylimides were studied, obtaining selectivity either to the cyclic compound or the hydrolysed keto derivative. This new system avoids the use of harmful solvents and employs very efficient and recoverable heterogeneous catalysts.

A highly active diradical cobalt(iii) catalyst for the cycloisomerization of alkynoic acids

The first cobalt-catalysed cycloisomerisation of alkynoic acids is reported, thanks to the design of a well-defined diradical cobalt(iii) catalyst, in the absence of any additives. The high efficiency, regioselectivity and chemoselectivity are comparable to those of noble metal-based systems. The unique reactivity might be attributed to second coordination sphere effects.

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.).

Dispersed gold nanoparticles supported in the pores of siliceous mesocellular foam: A catalyst for cycloisomerization of alkynoic acids to γ-alkylidene lactones

A versatile approach for the production of dispersed thiol-stabilized gold nanoparticles in the pores of siliceous mesocellular foam (MCF) is described. The reported method is based on an electrochemical oxidation of a gold surface generating oxidative Au

Silica-Supported Cationic Gold(I) Complexes as Heterogeneous Catalysts for Regio- and Enantioselective Lactonization Reactions

An efficient method for the synthesis of heterogeneous gold catalysts has been developed. These catalysts were easily assembled from readily available silica materials and gold complexes. The heterogeneous catalysts exhibited superior reactivity in various reactions where protodeauration is the rate-limiting step. Dramatic enhancement in regio- and enantioselectivity was observed when compared to the homogeneous unsupported gold catalyst. The catalysts are easily recovered and recycled up to 11 times without loss of enantioselectivity.

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

Pd-complex-bound amino acid-based supramolecular gel catalyst for intramolecular additioncyclization of alkynoic acids in water

An NCN-pincer Pd-complex-bound norvaline-based supramolecular gel showed efficient catalytic activities for the intramolecular additioncyclization of alkynoic acid and phenol derivatives in water to afford the corresponding ene-lactones in good to excelle