Jump to main content
Jump to site search

Issue 12, 2018
Previous Article Next Article

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

Author affiliations

Abstract

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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Jan 2018, accepted on 10 May 2018 and first published on 30 May 2018


Article type: Paper
DOI: 10.1039/C8CY00173A
Citation: Catal. Sci. Technol., 2018,8, 3073-3080
  •   Request permissions

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

    D. B. Eremin, D. A. Boiko, E. V. Borkovskaya, V. N. Khrustalev, V. M. Chernyshev and V. P. Ananikov, Catal. Sci. Technol., 2018, 8, 3073
    DOI: 10.1039/C8CY00173A

Search articles by author

Spotlight

Advertisements