88472-55-3Relevant academic research and scientific papers
Regio- and stereoselective dimerization of terminal alkynes to enynes catalyzed by a palladium/imidazolium system
Yang, Chuluo,Nolan, Steven P.
, p. 591 - 593 (2002)
A Palladium/imidazolium chloride system has been used to mediate the dimerization of terminal alkynes to enynes. The combination of 1 mol % Pd(OAc)2 and 2 mol % IMes·HCl in the presence of Cs2CO3 as base shows high activit
Carboxylate switch between hydro- and carbopalladation pathways in regiodivergent dimerization of alkynes
Zatolochnaya, Olga V.,Gordeev, Evgeniy G.,Jahier, Claire,Ananikov, Valentine P.,Gevorgyan, Vladimir
supporting information, p. 9578 - 9588 (2014/08/18)
Experimental and theoretical investigation of the regiodivergent palladium-catalyzed dimerization of terminal alkynes is presented. Employment of N-heterocyclic carbene-based palladium catalyst in the presence of phosphine ligand allows for highly regio- and stereoselective head-to-head dimerization reaction. Alternatively, addition of carboxylate anion to the reaction mixture triggers selective head-to-tail coupling. Computational studies suggest that reaction proceeds via the hydropalladation pathway favoring head-to-head dimerization under neutral reaction conditions. The origin of the regioselectivity switch can be explained by the dual role of carboxylate anion. Thus, the removal of hydrogen atom by the carboxylate directs reaction from the hydropalladation to the carbopalladation pathway. Additionally, in the presence of the carboxylate anion intermediate, palladium complexes involved in the head-to-tail dimerization display higher stability compared to their analogues for the head-to-head reaction. Track changer: The regiodivergent palladium-catalyzed dimerization of terminal alkynes was studied. High regio- and stereoselectivity was achieved for both head-to-head and head-to-tail dimerization reactions. Computational studies suggest hydropalladation to favor head-to-head dimerization under neutral conditions. Addition of carboxylate anions switches the reaction from hydropalladation to carbopalladation pathway securing head-to-tail coupling (see scheme).
Gold-catalyzed regioselective dimerization of aliphatic terminal alkynes
Sun, Sheng,Kroll, Julien,Luo, Yingdong,Zhang, Liming
scheme or table, p. 54 - 56 (2012/02/04)
A gold-catalyzed regioselective homodimerization of -aliphatic terminal alkynes is described. Bulky and less Lewis acidic t-BuXPhosAuNTf2 is the preferred catalyst, and the additive, anhydrous NaOAc, substantially facilitates the reaction. Geor
Activity of homobimetallic ruthenium alkylidene complexes on intermolecular [2+2+2] cyclotrimerisation reactions of terminal alkynes
Oeztuerk, Bengi Oezguen,Karabulut, Solmaz,Mamolu, Yavuz
experimental part, p. 257 - 263 (2012/01/12)
The activity of homobimetallic ruthenium alkylidene complexes, [(p-cymene)Ru(Cl)(μ-Cl)2Ru(Cl)(CHPh)(PCy3)] [Ru-I] and [(p-cymene)Ru(Cl)(μ-Cl)2Ru(Cl)(CHPh)(IPr)] [Ru-II], on intermolecular [2+2+2] cyclotrimerisation reactio
DIMERIZATION AND CODIMERIZATION OF MONOSUBSTITUTED ACETYLENES BY THE ACTION OF PALLADIUM COMPLEXES
Selimov, F. A.,Rutman, O. G.,Dzhemilev, U. M.
, p. 1621 - 1624 (2007/10/02)
The linear dimerization and codimerization of C5-C12 α-acetylenes with palladium catalyst were investigated systematically.It was shown that the catalyst system Pd(acac)2-PPh3-(C2H5)3Al can be used for selective transformation of α-acetylenes into the corresponding alkenylacetylenes with fairly high yields.
