Promoter effect of bicarbonate in hydrogenation of cinnamaldehyde catalyzed by a water-soluble Ru(II)-phosphine complex

Imre Szatmári, Gábor Papp, Ferenc Joó, Ágnes Kathó

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Abstract

The highly selective formation of cinnamalcohol in hydrogenation of trans-cinnamaldehyde with [{RuCl2(mtppms)2}2] + mtppms as catalyst (mtppms = monosulfonated triphenylphosphine) in aqueous solution was substantially accelerated by NaHCO3 (in 20–50 mol% quantities relative to cinnamaldehyde). More than double conversion compared to bicarbonate-free systems was observed at n(NaHCO3)/n(Ru) = 20. Prehydrogenation of the reaction mixture before the addition of cinnamaldehyde resulted in further rate increase (45.3% conversion vs. 13.1% in water). 1H, 13C and 31P NMR studies revealed that formate produced in hydrogenation of bicarbonate facilitated formation of trans-[Ru(H)2(H2O)(mtppms)3], a better catalyst than cis-fac-[Ru(H)2(H2O)(mtppms)3] which is the product of the reaction of [{RuCl2(mtppms)2}2] + mtppms with H2 in the absence of formate (or bicarbonate). Accordingly, NaHCO2 produced even higher rate increase than the same amount of NaHCO3.

Original languageEnglish
Pages (from-to)302-306
Number of pages5
JournalInorganica Chimica Acta
Volume472
DOIs
Publication statusPublished - Mar 1 2018

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Keywords

  • Hydrogenation
  • Isomerization
  • Monosulfonated triphenylphosphine (mtppms)
  • Ruthenium
  • Water-soluble

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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