Ten-fold boost of catalytic performance in thiol–yne click reaction enabled by a palladium diketonate complex with a hexafluoroacetylacetonate ligand

Autor:	Daniil A. Boiko, Dmitry B. Eremin, Victor N. Khrustalev, Valentine P. Ananikov, Victor M. Chernyshev, Eugenia V. Borkovskaya
Rok vydání:	2018
Předmět:	chemistry.chemical_classification 010405 organic chemistry Ligand Alkyne chemistry.chemical_element 010402 general chemistry Triple bond 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound Acetylene chemistry Polymer chemistry Click chemistry Chelation Palladium
Zdroj:	Catalysis Science & Technology. 8:3073-3080
ISSN:	2044-4761 2044-4753
DOI:	10.1039/c8cy00173a
Popis:	Palladium complexes with fluorinated acetylacetonate chelating ligands were studied as catalysts for alkyne hydrothiolation. A ten-fold increase in the catalytic efficiency was achieved by using 0.1 mol% of Pd(hfpd)2 complex (hfpd = hexafluoroacetylacetonate) with a variety of thiol–yne coupling partners. The principal possibility of a hundred-fold increase in the efficiency of Pd-catalyzed Markovnikov-type RSH addition with 0.01 mol% of the catalyst was successfully achieved with the hfpd ligand for the first time. The hexafluoroacetylacetonate chelating ligand not only enhanced the affinity of palladium centers to the triple bond of acetylene, but also stabilized the catalytic system against formation of insoluble polymeric [Pd(SPh)2]n species, thus ensuring that the reaction operates homogeneously. Utilizing other diketonate ligands resulted in cocktail-type catalysis with variable and poorly predictable contributions of homogeneous and heterogeneous pathways.
Databáze:	OpenAIRE
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