10401-10-2

Upstream product

• 124-38-9 carbon dioxide 
• 388061-72-1 3-[2-(trimethylsilylethynyl)]phenol 
• 10401-11-3 3-hydroxy phenylacetylene 
• 33696-06-9 3-benzoyloxybenzaldehyde 
• 16446-73-4 3-(chlorocarbonyl)phenyl acetate 
• 78589-63-6 3-(3-Acetoxy-phenyl)-propynoic acid methyl ester 

Downstream Products

• 10401-11-3 3-hydroxy phenylacetylene 

Relevant academic research and scientific papers

Fixation of CO2 as a carboxylic acid precursor by microcrystalline cellulose (MCC) supported Ag NPs: A more efficient, sustainable, biodegradable and eco-friendly catalyst

Silver nanoparticles supported on microcrystalline cellulose (Ag NPs@MCC), an active catalyst, has been discovered for the direct carbonylation of terminal alkynes with CO2 into carboxylic acid under mild and sustainable reaction conditions. The stabilized Ag NPs show higher distribution with a uniform particle size. The catalyst was characterized by PXRD, SEM, TEM, HR-TEM, EDS, EDX, ICP-AES and XPS analysis. The Ag NPs@MCC material was found to be more efficient, shows excellent dispersion in various solvents and is biodegradable. The solvent effects on carbonylation of terminal alkynes were well studied both experimentally and computationally. Furthermore, the present catalyst can be recycled in up to five catalytic cycles without significant loss of its activity and is also applicable for the gram scale carbonylation of terminal alkynes.

Carboxylation of terminal alkynes promoted by silver carbamate at ambient pressure

Transition metal carbamates constitute a class of compounds with unique properties, however their catalytic potential has been sparingly explored so far. The easily available silver N,N-dimethylcarbamate, Ag(O2CNMe2), worked as a catalyst in the carboxylation reaction of terminal alkynes with CO2 at atmospheric pressure. Different reaction parameters (solvent, base, temperature, time and the amount of catalyst) were investigated in order to establish the optimal conditions.

Carboxylation of alkynylsilanes with carbon dioxide mediated by cesium fluoride in DMSO

The facile syntheses of a variety functionalized propiolic acids were achieved by carboxylation of alkynylsilanes with carbon dioxide mediated by cesium fluoride under ambient conditions. This journal is The Royal Society of Chemistry 2013.

Organocatalytic Strategy for the Fixation of CO2via Carboxylation of Terminal Alkynes

An organocatalytic strategy for the direct carboxylation of terminal alkynes with CO2 has been developed. The combined use of a bifunctional organocatalyst and Cs2CO3 resulted in a robust catalytic system for the preparation of a range of propiolic acid derivatives in high yields with broad substrate scope using CO2 at atmospheric pressure under mild temperatures (60 °C). This work has demonstrated that this organocatalytic method offers a competitive alternative to metal catalysis for the carboxylation of terminal alkynes and CO2. In addition, this protocol was suitable for the three-component carboxylation of terminal alkynes, alkyl halides, and CO2.

Carbon dioxide capture and use: Organic synthesis using carbon dioxide from exhaust gas

A carbon capture and use (CCU) strategy was applied to organic synthesis. Carbon dioxide (CO2) captured directly from exhaust gas was used for organic transformations as efficiently as hyper-pure CO2 gas from a commercial source, even for highly air- and moisture-sensitive reactions. The CO2 capturing aqueous ethanolamine solution could be recycled continuously without any diminished reaction efficiency. Exhaust gas is good enough! Carbon dioxide captured directly from exhaust gas was used for organic syntheses (see picture) as efficiently as hyper-pure CO2 gas from a commercial source, even for highly air- and moisture-sensitive reactions. The CO2 capturing aqueous ethanolamine solution could be recycled continuously without any diminished reaction efficiency. Copyright

Carboxylation of terminal alkynes with carbon dioxide catalyzed by Poly(N-Heterocyclic Carbene)-supported silver nanoparticles

An N-heterocyclic carbene (NHC) polymer supported silver nanoparticle catalyst system was developed. The novel nano-composite catalyst demonstrated very high activity and excellent stability and reusability in the carboxylation of terminal alkynes with carbon dioxide at ambient conditions. The unique N-heterocyclic carbene polymer and silver nanoparticle composite structure provided a synergistic effect on activation of terminal alkynes and carbon dioxide that contributed to the high catalytic activity. The poly-NHC-silver catalyst exhibited excellent substrate generality and tolerance to various functionalities. In addition, the catalyst is stable to air and moisture and can be easily recovered and reused. Copyright

The direct carboxylation of terminal alkynes with carbon dioxide

A simple and straight-forward method has been developed for direct carboxylation of terminal alkynes using CO2 as the C1 carbon feedstock. The direct C-H bond functionalization is achieved with Cs 2CO3 as the base and in the absence of transition metal catalyst. Various propiolic acids were synthesized in good to excellent yields with a wide substrate scope and a good functional groups tolerance. This is a more atom- and step-economic protocol with great potential in practical application.

CARBOXYLATION OF TERMINAL ALKYNES

The present invention describes a process for converting a terminal alkyne into an alkynoic acid. In this process the alkyne is exposed to carbon dioxide in the presence of a copper (I) species, a base and a complexing agent capable of complexing copper (I).

Ligand-free Ag(I)-catalyzed carboxylation of terminal alkynes with CO 2

Chemical equations presented. A convenient approach to selectively prepare a wide range of functionalized propiolic acids was developed by AgI-catalyzed carboxylation of terminal alkynes using carbon dioxide as carboxylative agent under ligand-free conditions.

NOUVEAU MODE DE CYCLYSATION DE CETO-YLURES. APPLICATION A UNE SYNTHESE IGINALE D'ACYL-3 HYDROXY-4-COUMARINES ET DE L'HYDROXY-11 BENZO-(b) 12 XANTHONE-12

The thermal decomposition of keto-ylides resulting from the reaction of m- and p-acetoxy benzoyl chlorides with Ph3P=CH-COOMe leads, after saponification to m- and p-phenylpropiolic acid respectively.Ortho substitution by an acyl group generally changes the orientation of the reaction.Thus o-acetoxy-, benzoyloxy- or phenylacetoxy benzoyl chlorides respectively afford: and (R=Me,Ph) in satisfactory yields.Saponification of the first and second ones gives: (R=Me, Ph).This constitutes a new, convenient route to 3-acyl 4-hydroxy cumarins and 11-hydroxy 12H-benzoxanthene 12-one.Formation of these last products involves the carbonyl of the acyloxy-substituent and not of the acyl chloride as previously observed in these series.