Homogeneous and Semi-Heterogeneous Magnetically Retrievable Bis-N-Heterocyclic Carbene Rhodium(I) Based Catalysts for Selective Hydroaminomethylation Reactions

Bishnu Dutta, Rony Schwarz, Suheir Omar, Suzana Natour, Raed Abu-Reziq*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

The preparation of various bis-N-heterocyclic carbene (bis-NHC) complexes of rhodium and their application in the hydroaminomethylation of vinyl arenes was investigated. Various reaction parameters such as solvent, temperature, and pressure were tested, and the optimized protocol was applied to a wide variety of vinyl arenes and amines to afford the corresponding amines in good yields with high selectivity towards the branched product. The bis-NHC-based catalyst demonstrated superior reactivity and selectivity compared to catalysts containing bidentate phosphine or monodentate NHC ligands. A triethoxysilyl-functionalized bis-NHC ligand was immobilized on magnetic nanoparticles and then utilized to bind a rhodium catalyst. The resulting catalytic system was successfully employed in hydroaminomethylation reactions. The catalyst exhibited excellent reactivity, high selectivity, and was simply recovered from the reaction medium by applying an external magnetic field.

Original languageAmerican English
Pages (from-to)1961-1969
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number9
DOIs
StatePublished - Mar 2015

Bibliographical note

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Carbene ligands
  • Hydroaminomethylation
  • Nanoparticles
  • Rhodium
  • Semi-heterogeneous catalysis

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