5962-81-2Relevant articles and documents
Copper-Catalyzed, Stereoselective Bis-trifluoromethylthiolation of Propiolic Acid Derivatives with AgSCF3
Pan, Shen,Li, Huan,Huang, Yangen,Xu, Xiu-Hua,Qing, Feng-Ling
, p. 3247 - 3250 (2017)
A copper-catalyzed chemo- and stereoselective oxidative bis-trifluoromethylthiolation of propiolic acid derivatives was achieved by using carboxylic acid as the activating group and formic acid as a cosolvent. The reaction of propiolic acid derivatives and AgSCF3 in the presence of (NH4)2S2O8 and catalytic Cu(OAc)2 in MeCN/HCO2H afforded bis-trifluoromethylthiolated acrylic acids in moderate to excellent yields with E selectivity. Further derivatization of the resultant products gave a series of polysubstituted SCF3-containing alkenes.
Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System
Yuan, Ye,Chen, Cheng,Zeng, Cheng,Mousavi, Bibimaryam,Chaemchuen, Somboon,Verpoort, Francis
, p. 882 - 887 (2017/03/13)
A carboxylation of terminal alkynes with carbon dioxide (CO2) at ambient conditions was developed in situ using a series of N-heterocyclic carbene (NHC) precursors and Ag2O. The unique structure of NHCs largely increases the solubility of active Ag species and meanwhile activates CO2 by forming the NHC–CO2 adduct. This novel catalytic system demonstrated quite low Ag loading, very high activities, wide substrate generality and excellent tolerance for a variety of functionalities. In addition, avoiding cumbersome synthesis procedures, processing, and reserving of the photosensitive Ag complex, this system could be stored and operated as straightforward as the inorganic Ag salt catalysts.
PROCESS FOR PREPARING A PROPIOLIC ACID OR A DERIVATIVE THEREOF
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Paragraph 0140; 0141; 0142; 0143, (2014/02/15)
The invention relates to a process for preparing a propiolic acid or a derivative thereof by reacting a terminal alkyne with carbon dioxide, which comprises performing the reaction in the presence of a base and a copper complex, especially a copper (I) complex having at least one ligand, at least one of the ligands of the copper complex being selected from monodentate ligands which have an aminic or iminic nitrogen atom capable of coordination with copper, and polydentate ligands having at least two atoms or atom groups which are capable of simultaneous coordination with copper and are selected from nitrogen, oxygen, sulfur, phosphorus and carbene carbon.
Carbon dioxide capture and use: Organic synthesis using carbon dioxide from exhaust gas
Kim, Seung Hyo,Kim, Kwang Hee,Hong, Soon Hyeok
supporting information, p. 771 - 774 (2014/01/23)
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
Ligand-free Ag(I)-catalyzed carboxylation of terminal alkynes with CO 2
Zhang, Xiao,Zhang, Wen-Zhen,Ren, Xiang,Zhang, Lin-Lin,Lu, Xiao-Bing
supporting information; experimental part, p. 2402 - 2405 (2011/06/25)
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.
Synthesis of propiolic acids via copper-catalyzed insertion of carbon dioxide into the C-H bond of terminal alkynes
Goossen, Lukas J.,Rodriguez, Nuria,Manjolinho, Filipe,Lange, Paul P.
supporting information; experimental part, p. 2913 - 2917 (2011/02/22)
A highly effective copper catalyst has been developed that promotes the insertion of carbon dioxide into the C-H bond of terminal alkynes under unprecedentedly mild conditions. For the first time, propiolic acids can thus be synthesized in excellent yields from alkynes and carbon dioxide in the presence of the mild base cesium carbonate. The catalyst, (4,7-diphenyl-1,10- phenanthroline)bis[tris(4-fluorophenyl)phosphine]copper(I) nitrate, is easy accessible and relatively stable against air and water. Copyright
Isomerization of alkyl branched alkynoic acids
Abrams, Suzanne R.
, p. 457 - 463 (2007/10/02)
Acetylenic acids are isomerized by alkali metal amides of 1,3-diaminopropene to 3,5-dienoic acids.An acid with a methyl branch at C-3 separating the carboxyl from the triple bond is rearranged to a mixture of the terminal alkynoic acid and two isomeric 3,
