Highly active metal-free catalysts for hydrogenation of unsaturated nitrogen-containing compounds

Victor Sumerin, Konstantin Chernichenko, Martin Nieger, Markku Leskelä, Bernhard Rieger, Timo Repo

Research output: Contribution to journalArticlepeer-review

160 Scopus citations

Abstract

New highly active ansa-ammonium borate catalysts for the direct metal-free hydrogenation of imines were prepared by tuning of the basicity and steric bulkiness of their amine moieties. The highest catalytic activity among previously reported organocatalytic systems was shown for a wide range of nitrogen-containing substrates. The first example of asymmetric imine hydrogenation based on the ansa-ammonium borate concept was demonstrated. Furthermore, effective catalyst recovery by extraction of the acidic solution with an organic solvent followed by dehydration with TMSBr was elaborated. The initial findings highlight the development of more effective chiral ansa-ammonium borates for enantioselective hydrogenation. Therefore, the progress achieved in the ansa-ammonium borate concept makes it very promising for further elaboration with the aim to obtain industrially applicable catalysts.

Original languageEnglish
Pages (from-to)2093-2110
Number of pages18
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number11-12
DOIs
StatePublished - Aug 2011

Keywords

  • amines
  • boranes
  • homogeneous catalysis
  • hydrogenation
  • organocatalysis

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