1595-70-6

Upstream product

• 105-07-7 4-cyanobenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 1187388-08-4 4-(4-cyanophenyl)-4-hydroxybut-2-ynoic acid 
• 75-24-1 trimethylaluminum 
• 1066-26-8 sodium acetylide 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 452922-46-2 1-(4-cyanophenyl)-2-propyn-1-one 
• 41917-85-5 p-cyanocinnamaldehyde 
• 1595-57-9 1-p-Carboxyphenylhexa-2,4-di-in-1-ol 
• 1595-68-2 1-(p-Carboxyphenyl)-prop-2-in-1-ol 
• 179249-07-1 Chloro-acetic acid (R)-1-(4-cyano-phenyl)-prop-2-ynyl ester 
• 179249-00-4 Chloro-acetic acid 1-(4-cyano-phenyl)-prop-2-ynyl ester 
• 1595-69-3 p-(1-Hydroxyprop-2-inyl)-benzamid 

Relevant academic research and scientific papers

Relay Catalysis to Synthesize β-Substituted Enones: Organocatalytic Substitution of Vinylogous Esters and Amides with Organoboronates

Organocatalysis was shown to facilitate conjugate additions to vinylogous esters and amides for the first time. Subsequent elimination of a β-alcohol or amine provided π-conjugated β-substituted enones. Remarkably, nucleophile addition to the electron-rich vinylogous substrates is more rapid than classical enones, forming monosubstituted products. A doubly organocatalytic (organic diol and methyl aniline) conjugate addition synthesized the products directly from alkynyl ketones. Both of these catalytic transformations are orthogonal to transition metal catalysis, allowing for good yields, easily accessible or commercially available reagents, high selectivity, reagent recovery and recyclability, facile scalability, and exceptional functional group tolerance.

Coupling-Isomerization-Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2-(Hydroxymethylene)indenones

A Pd/Cu-catalyzed base mediated domino process of ortho-halo (hetero)aryl carboxaldehydes and propargyl alcohols unexpectedly furnish 2-(hydroxymethylene)indenones in good to excellent yield as a result of a coupling-isomerization-cycloisomerization reaction (CICIR). In addition, the title compounds constitute an interesting class of luminophores with tunable emission solvatochromicity.

Gem-Digold Acetylide Complexes for Catalytic Intermolecular [4 + 2] Cycloaddition: Having Two Gold Centers Is Better for Asymmetric Catalysis

Gold(I)-catalyzed highly enantioselective intermolecular [4 + 2] cycloaddition is shown with ynones and cyclohexadiene. Various bicyclo[2.2.2]octadiene derivatives are produced in high yields (up to 99%) with good enantioselectivity (up to 96% ee). Key to the success is generation of the gem-digold terminal alkyne as a catalytic on-cycle species. As proof of the gem-digold catalysis, a positive nonlinear effect is clarified between the ee's of the ligand and the cycloadduct.

Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations

An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution p

Catalytic decarboxylation of 2-alkynoic acids

(Chemical Equation Presented) A very efficient protocol enabling catalytic decarboxylation of a wide range of 2-alkynoic acids is described. The reaction conditions and the scope of the process are examined. The method is further utilized in a model decar

Synthesis, structure and emission properties of spirocyclic benzofuranones and dihydroindolones: A domino insertion-coupling-isomerization-Diels-Alder approach to rigid fluorophores

An alkynoyl ortho-iodo phenolester or alkynoyl ortho-iodo anilides and propargyl allyl ethers react under Sonogashira coupling conditions in the sense of an insertion-coupling-isomerization-Diels-Alder hetero domino reaction to furnish (tetrahydroisobenzo

Aryl propargylic alcohols of high enantiomeric purity via lipase catalyzed resolutions

A variety of substituted aryl propargylic alcohols were prepared via lipase catalyzed resolutions, the enantioselective hydrolysis of the corresponding esters being the method of choice.