Hydrogenation and redox isomerization of allylic alcohols catalyzed by a new water-soluble Pd-tetrahydrosalen complex

Krisztina Voronova, Mihály Purgel, Antal Udvardy, Attila C. Bényei, Ágnes Kathó, Ferenc Joó

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

For applications in aqueous media, sulfonated tetrahydrosalen (sulfosalan, HSS) was synthesized by sulfonation of tetrahydrosalen in fuming sulfuric acid. The Pd(II) complex of this ligand, [Pd(HSS)], showed outstanding activity in hydrogenation and redox isomerization of allylic alcohols in homogeneous aqueous solutions or in aqueous-organic biphasic systems (for oct-1-en-3-ol TOF(hydrogenation) = 1580 h-1, TOF(redox isomerization) = 400 h -1). DFT calculations revealed that H2 is activated heterolytically, resulting in a Pd(II)-hydride complex, [Pd(H)(HSS-Hphen)], in which one of the phenolate oxygens is protonated. Both hydrogenation and redox isomerization take place via concerted transfer of a proton and a hydride from the hydrogenated catalyst to the allylic alcohol.

Original languageEnglish
Pages (from-to)4391-4401
Number of pages11
JournalOrganometallics
Volume32
Issue number15
DOIs
Publication statusPublished - Aug 12 2013

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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