Jump to main content
Jump to site search

Issue 4, 2017, Issue in Progress
Previous Article Next Article

Amphipathic monolith-supported palladium catalysts for chemoselective hydrogenation and cross-coupling reactions

Author affiliations

Abstract

A palladium catalyst immobilized on an amphipathic and monolithic polystyrene–divinylbenzene polymer bearing strongly acidic cation exchange functions (sulfonic acid moieties) (Pd/CM) was developed. It was used as a catalyst for hydrogenation and ligand-free cross-coupling reactions, such as the Suzuki–Miyaura, Mizoroki–Heck, and copper- and amine-free Sonogashira-type reactions, together with a palladium catalyst supported on monolithic polymer (Pd/AM) bearing basic anion exchange functions (ammonium salt moieties), which has been in practical use for the decomposition of hydrogen peroxide produced as a byproduct during the manufacture of ultrapure water. While the Pd/CM was highly active as a catalyst for the hydrogenation and a variety of reducible functional groups could be reduced, the use of Pd/AM led to a unique chemoselective hydrogenation. Aromatic carbonyl groups were tolerant under the Pd/AM-catalyzed hydrogenation conditions, although benzyl esters, benzyl ethers, and N-Cbz groups could be smoothly hydrocracked. The cross-coupling reactions readily proceeded using either catalyst. The palladium leaching from the Pd/CM into the reaction media was never observed during the Sonogashira-type reaction, which was hardly achieved by other palladium-supported heterogeneous catalysts due to the good affinity of the palladium species with alkynes.

Graphical abstract: Amphipathic monolith-supported palladium catalysts for chemoselective hydrogenation and cross-coupling reactions

Back to tab navigation

Supplementary files

Publication details

The article was received on 05 Oct 2016, accepted on 10 Dec 2016 and first published on 12 Jan 2017


Article type: Paper
DOI: 10.1039/C6RA24769E
Citation: RSC Adv., 2017,7, 1833-1840
  • Open access: Creative Commons BY license
  •   Request permissions

    Amphipathic monolith-supported palladium catalysts for chemoselective hydrogenation and cross-coupling reactions

    Y. Monguchi, F. Wakayama, S. Ueda, R. Ito, H. Takada, H. Inoue, A. Nakamura, Y. Sawama and H. Sajiki, RSC Adv., 2017, 7, 1833
    DOI: 10.1039/C6RA24769E

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements