55795-29-4Relevant academic research and scientific papers
A green and recyclable CuSO4·5H2O/ionic liquid catalytic system for the CO2-promoted hydration of propargyl alcohols: an efficient assembly of α-hydroxy ketones
Yuan, Ye,Hu, Jia,Wang, Yu,Huang, Leilei,Zheng, Jiayun,Zhao, Yufeng,Chen, Yiyun,Chen, Cheng,Verpoort, Francis
, p. 561 - 570 (2021/12/03)
α-Hydroxy ketones are important building blocks in biological, pharmaceutical and synthetic chemistry. In this work, diverse α-hydroxy ketones were efficiently constructed through the CO2-promoted hydration process of propargyl alcohols, which was catalyzed by a system consisted of economical CuSO4·5H2O and a green 1-butyl-3-methylimidazolium acetate ionic liquid. Particularly, this catalytic system exhibited excellent activity under atmospheric CO2 or even mimetic flue gas (20 vol% of CO2). Moreover, this system employed the lowest metal loading ever reported (0.004–0.25 mol%) meanwhile reached the highest turnover number (11700) for the target hydration reaction. Additionally, this is the first reported Cu catalytic system with reliable recyclability, which could be easily reused at least 6 times with yields higher than 85%.
Thermodynamic favorable CO2 conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method
Han, Li-Hua,Li, Jing-Yuan,Song, Qing-Wen,Zhang, Kan,Zhang, Qian-Xia,Sun, Xiao-Fang,Liu, Ping
supporting information, p. 341 - 344 (2019/07/04)
Organocatalysis represents a promising field in chemical fixation of CO2. Herein, a facile metal-free strategy was reported for the one-pot preparation of cyclic carbonates and α-hydroxy ketones from vicinal diols, propargylic alcohols and CO2. Wide scope of vicinal diols and propargylic alcohols was demonstrated to be efficient under the DBU-catalyzed conditions. A plausible mechanism was proposed, which included detailed main and side reactions under the metal-free conditions.
Synthesis of Α-hydroxy ketones by copper(I)-catalyzed hydration of propargylic alcohols: CO2 as a cocatalyst under atmospheric pressure
Zhou, Zhi-Hua,Zhang, Xiao,Huang, Yong-Fu,Chen, Kai-Hong,He, Liang-Nian
, p. 1345 - 1351 (2019/08/07)
Inexpensive and efficient Cu(I) catalysis is reported for the synthesis of α-hydroxy ketones from propargylic alcohols, CO2, and water via tandem carboxylative cyclization and nucleophilic addition reaction. Notably, hydration of propargylic alcohols can be carried out smoothly under atmospheric CO2 pressure, generating a series of α-hydroxy ketones efficiently and selectively. This strategy shows great potential for the preparation of valuable α-hydroxy ketones by using CO2 as a crucial cocatalyst under mild conditions.
Effective guanidine-catalyzed synthesis of carbonate and carbamate derivatives from propargyl alcohols in supercritical carbon dioxide
Ca', Nicola Della,Gabriele, Bartolo,Ruffolo, Giuseppe,Veltri, Lucia,Zanetta, Tito,Costa, Mirco
supporting information; experimental part, p. 133 - 146 (2011/04/18)
The reactions of propargyl alcohols with carbon dioxide in supercritical carbon dioxide or in acetonitrile with gaseous carbon dioxide in the presence of organic bases as catalysts have been examined. Bicyclic guanidines are effective catalysts for the formation of α-methylene cyclic carbonates under mild reaction conditions. Oxoalkyl carbonates, oxoalkyl carbamates or α-methyleneoxazolidinones are obtained in high yields and good selectivities in one-step starting from propargyl alcohols and an external nucleophile (alcohols or amines) using bicyclic guanidines as catalysts in supercritical carbon dioxide. Propargylic diols under the same reaction conditions underwent a rearrangement process instead of carbon dioxide insertion whereas in the presence of an external nucleophile the formation of oxocarbonates, oxocarbamates or cyclic carbamates was achieved in satisfactory yields.
Analogues of Acifran: Agonists of the high and low affinity niacin receptors, GPR109a and GPR109b
Jung, Jae-Kyu,Johnson, Benjamin R.,Duong, Tracy,Decaire, Marc,Uy, Jane,Gharbaoui, Tawfik,Boatman, P. Douglas,Sage, Carleton R.,Chen, Ruoping,Richman, Jeremy G.,Connolly, Daniel T.,Semple, Graeme
, p. 1445 - 1448 (2007/10/03)
Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.
Pyrrole Annulation onto Aldehydes and Ketones via Palladium-Catalyzed Reactions
Trost, Barry M.,Keinan, Ehud
, p. 2741 - 2746 (2007/10/02)
α-Dicarbonyl systems reacted with vinylmagnesium bromide and acetic anhydride to give α-acetoxy-α-vinylalkanones.These substrates react with benzylamine in the presence of tetrakis(triphenylphosphine)palladium to give N-benzylpyrroles with substituents in the two and/or three position.The functiodifferentiated synthesis of α-dicarbonyl compounds from ketones makes this a pyrrole annulation onto any α-methylene carbonyl system.
