The dual role of cis-[RuCl 2(dmso) 4] in the synthesis of new water-soluble Ru(II)-phosphane complexes and in the catalysis of redox isomerization of allylic alcohols in aqueous-organic biphasic systems

Antal Udvardy, A. Bényei, A. Kathó

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15 Citations (Scopus)

Abstract

New air-stable, water-soluble Ru(II)-phosphane complexes were synthesized in high purity by the reaction of cis-[RuCl 2(dmso) 4] with 2 equivalents of 1,3,5-triaza-7-phosphaadamantane (pta) and its N-methyl and N-benzyl derivatives (pta-Me and pta-Bn, respectively). All new complexes were characterized by elementary analysis and spectroscopic methods (NMR, ESI-MS) and the molecular structures of cis-cis-trans-[RuCl 2(dmso) 2(pta) 2], cis-cis-trans-[RuCl 2(dmso) 2(pta-H) 2]Cl 2 (obtained in acidic solutions) and that of cis-cis-trans-[RuCl 2(dmso) 2(pta-Me) 2](CF 3SO 3) 2 were determined by single crystal X-ray diffraction. Under mild conditions, cis-[RuCl 2(dmso) 4] actively catalyzed the transformation of allylic alcohols into the corresponding ketones with 100% selectivity while in the same reaction the new Ru(II)-pta complexes showed moderate activity and selectivity.

Original languageEnglish
Pages (from-to)116-122
Number of pages7
JournalJournal of Organometallic Chemistry
Volume717
DOIs
Publication statusPublished - Oct 15 2012

Fingerprint

phosphine
Isomerization
Molecular Structure
Ketones
Catalysis
X-Ray Diffraction
Molecular structure
isomerization
Oxidation-Reduction
catalysis
alcohols
Alcohols
selectivity
Air
Nuclear magnetic resonance
Single crystals
Derivatives
X ray diffraction
Water
synthesis

Keywords

  • Allylic alcohols
  • Biphasic catalysis
  • Isomerization
  • Ruthenium
  • Water-soluble phosphanes

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Biochemistry

Cite this

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title = "The dual role of cis-[RuCl 2(dmso) 4] in the synthesis of new water-soluble Ru(II)-phosphane complexes and in the catalysis of redox isomerization of allylic alcohols in aqueous-organic biphasic systems",
abstract = "New air-stable, water-soluble Ru(II)-phosphane complexes were synthesized in high purity by the reaction of cis-[RuCl 2(dmso) 4] with 2 equivalents of 1,3,5-triaza-7-phosphaadamantane (pta) and its N-methyl and N-benzyl derivatives (pta-Me and pta-Bn, respectively). All new complexes were characterized by elementary analysis and spectroscopic methods (NMR, ESI-MS) and the molecular structures of cis-cis-trans-[RuCl 2(dmso) 2(pta) 2], cis-cis-trans-[RuCl 2(dmso) 2(pta-H) 2]Cl 2 (obtained in acidic solutions) and that of cis-cis-trans-[RuCl 2(dmso) 2(pta-Me) 2](CF 3SO 3) 2 were determined by single crystal X-ray diffraction. Under mild conditions, cis-[RuCl 2(dmso) 4] actively catalyzed the transformation of allylic alcohols into the corresponding ketones with 100{\%} selectivity while in the same reaction the new Ru(II)-pta complexes showed moderate activity and selectivity.",
keywords = "Allylic alcohols, Biphasic catalysis, Isomerization, Ruthenium, Water-soluble phosphanes",
author = "Antal Udvardy and A. B{\'e}nyei and A. Kath{\'o}",
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T1 - The dual role of cis-[RuCl 2(dmso) 4] in the synthesis of new water-soluble Ru(II)-phosphane complexes and in the catalysis of redox isomerization of allylic alcohols in aqueous-organic biphasic systems

AU - Udvardy, Antal

AU - Bényei, A.

AU - Kathó, A.

PY - 2012/10/15

Y1 - 2012/10/15

N2 - New air-stable, water-soluble Ru(II)-phosphane complexes were synthesized in high purity by the reaction of cis-[RuCl 2(dmso) 4] with 2 equivalents of 1,3,5-triaza-7-phosphaadamantane (pta) and its N-methyl and N-benzyl derivatives (pta-Me and pta-Bn, respectively). All new complexes were characterized by elementary analysis and spectroscopic methods (NMR, ESI-MS) and the molecular structures of cis-cis-trans-[RuCl 2(dmso) 2(pta) 2], cis-cis-trans-[RuCl 2(dmso) 2(pta-H) 2]Cl 2 (obtained in acidic solutions) and that of cis-cis-trans-[RuCl 2(dmso) 2(pta-Me) 2](CF 3SO 3) 2 were determined by single crystal X-ray diffraction. Under mild conditions, cis-[RuCl 2(dmso) 4] actively catalyzed the transformation of allylic alcohols into the corresponding ketones with 100% selectivity while in the same reaction the new Ru(II)-pta complexes showed moderate activity and selectivity.

AB - New air-stable, water-soluble Ru(II)-phosphane complexes were synthesized in high purity by the reaction of cis-[RuCl 2(dmso) 4] with 2 equivalents of 1,3,5-triaza-7-phosphaadamantane (pta) and its N-methyl and N-benzyl derivatives (pta-Me and pta-Bn, respectively). All new complexes were characterized by elementary analysis and spectroscopic methods (NMR, ESI-MS) and the molecular structures of cis-cis-trans-[RuCl 2(dmso) 2(pta) 2], cis-cis-trans-[RuCl 2(dmso) 2(pta-H) 2]Cl 2 (obtained in acidic solutions) and that of cis-cis-trans-[RuCl 2(dmso) 2(pta-Me) 2](CF 3SO 3) 2 were determined by single crystal X-ray diffraction. Under mild conditions, cis-[RuCl 2(dmso) 4] actively catalyzed the transformation of allylic alcohols into the corresponding ketones with 100% selectivity while in the same reaction the new Ru(II)-pta complexes showed moderate activity and selectivity.

KW - Allylic alcohols

KW - Biphasic catalysis

KW - Isomerization

KW - Ruthenium

KW - Water-soluble phosphanes

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