A highly efficient procedure for hydroformylation and hydroamino-vinylation of methyl acrylate

Matthew L. Clarke, Geoffrey J. Roff

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

Methyl acrylate has been hydroformylated to the branched aldehyde with essentially perfect regio-selectivity and extraordinarily high average turnover frequencies ( up to 4000 h(-1)). Using 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane based Rh catalyst with a substrate to catalyst ratio of 10 000, hydroformylation in excellent yield was achieved with complete branched selectivity in around 2 h. Performing this reaction in the presence of aromatic amines gave very high yields of the corresponding enamines in a quick one pot domino hydroaminovinylation reaction. Remarkably, this latter reaction works best under solvent-free conditions.

Original languageEnglish
Pages (from-to)792-796
Number of pages5
JournalGreen Chemistry
Volume9
DOIs
Publication statusPublished - 2007

Keywords

  • CATALYZED ASYMMETRIC HYDROFORMYLATION
  • RHODIUM(I) COMPLEXES
  • ENANTIOSELECTIVE HYDROFORMYLATION
  • SUPERCRITICAL CO2
  • PHOSPHITE LIGANDS
  • OLEFINS
  • DERIVATIVES
  • CHEMISTRY
  • ESTERS

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