Chemoselective aerobic oxidation of unprotected diols catalyzed by Pd-(NHC) (NHC = N-heterocyclic carbene) complexes

Lorenzo Bettucci, Claudio Bianchini, Werner Oberhauser, Tsun Hung Hsiao, Hon Man Lee

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Neutral Pd(X)(η3-allyl) (X = Cl, OAc (acetate)) complexes bearing mono-coordinating NHC ligands have been synthesized, characterized and employed to catalyze the aerobic oxidation of unprotected 1,2- and 1,3-diols selectively to hydroxy ketones. A comparison of the catalytic performance of these precursors with a reference system has shown that the precursor with the ligands N,N′-bis(adamantyl)imidazol-2-ylidene and chloride is the most efficient for the chemoselective oxidation of 1,2-diols is concerned. High-pressure 1H NMR (HPNMR) experiments in combination with catalytic batch reactions have provided valuable information on the activation of the precursor as well as on the stability of the catalysts.

Original languageEnglish
Pages (from-to)63-72
Number of pages10
JournalJournal of Molecular Catalysis A: Chemical
Volume322
Issue number1-2
DOIs
Publication statusPublished - 2010 May 1

Fingerprint

carbenes
Bearings (structural)
Ligands
Oxidation
ligands
oxidation
reference systems
Ketones
imidazoles
ketones
Chlorides
acetates
Acetates
Chemical activation
chlorides
Nuclear magnetic resonance
activation
catalysts
nuclear magnetic resonance
Catalysts

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

Cite this

Bettucci, Lorenzo ; Bianchini, Claudio ; Oberhauser, Werner ; Hsiao, Tsun Hung ; Lee, Hon Man. / Chemoselective aerobic oxidation of unprotected diols catalyzed by Pd-(NHC) (NHC = N-heterocyclic carbene) complexes. In: Journal of Molecular Catalysis A: Chemical. 2010 ; Vol. 322, No. 1-2. pp. 63-72.
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Chemoselective aerobic oxidation of unprotected diols catalyzed by Pd-(NHC) (NHC = N-heterocyclic carbene) complexes. / Bettucci, Lorenzo; Bianchini, Claudio; Oberhauser, Werner; Hsiao, Tsun Hung; Lee, Hon Man.

In: Journal of Molecular Catalysis A: Chemical, Vol. 322, No. 1-2, 01.05.2010, p. 63-72.

Research output: Contribution to journalArticle

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AU - Bettucci, Lorenzo

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AB - Neutral Pd(X)(η3-allyl) (X = Cl, OAc (acetate)) complexes bearing mono-coordinating NHC ligands have been synthesized, characterized and employed to catalyze the aerobic oxidation of unprotected 1,2- and 1,3-diols selectively to hydroxy ketones. A comparison of the catalytic performance of these precursors with a reference system has shown that the precursor with the ligands N,N′-bis(adamantyl)imidazol-2-ylidene and chloride is the most efficient for the chemoselective oxidation of 1,2-diols is concerned. High-pressure 1H NMR (HPNMR) experiments in combination with catalytic batch reactions have provided valuable information on the activation of the precursor as well as on the stability of the catalysts.

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