Selective Hydrogenation of α,β-Unsaturated Aldehydes and Ketones by Air-Stable Ruthenium NNS Complexes

Pim Puylaert, Richard van Heck, Yuting Fan, Anke Spannenberg, Wolfgang Baumann, Matthias Beller, Jonathan Medlock, Werner Bonrath, Laurent Lefort, Sandra Hinze, Johannes G. de Vries

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

The selective hydrogenation of the carbonyl functionality of α,β-unsaturated aldehydes and ketones is catalysed by ruthenium dichloride complexes bearing a tridentate NNS ligand as well as triphenylphosphine. The tridentate ligand backbone is flexible, as evidenced by the equilibrium observed in solution between the cis- and trans-isomers of the dichloride precatalysts, as well as crystal structures of several of these complexes. The complexes are activated by base in the presence of hydrogen and readily hydrogenate carbonyl functionalities under mild conditions. Despite the activation by base, side reactions are negligible, even for aldehyde substrates, because of the low amount of base. Thus, the corresponding allylic alcohols can be isolated in very good yields on a 10–25 mmol scale. Turnover numbers up to 200 000 were achieved.

Original languageEnglish
Pages (from-to)8473-8481
Number of pages9
JournalChemistry - A European Journal
Volume23
Issue number35
DOIs
StatePublished - 22 Jun 2017
Externally publishedYes

Keywords

  • alcohols
  • homogeneous catalysis
  • hydrogenation
  • ligand
  • ruthenium

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