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Publication Detail
Sulfur-Directed Olefin Oxidations: Observation of Divergent Reaction Mechanisms in the Palladium-Mediated Acetoxylation of Unsaturated Thioacetals
  • Publication Type:
    Journal article
  • Publication Sub Type:
    Article
  • Authors:
    Mann SE, Aliev AE, Tizzard GJ, Sheppard TD
  • Publisher:
    AMER CHEMICAL SOC
  • Publication date:
    11/04/2011
  • Pagination:
    1772, 1775
  • Journal:
    ORGANOMETALLICS
  • Volume:
    30
  • Issue:
    7
  • Print ISSN:
    0276-7333
  • Language:
    EN
  • Keywords:
    CATALYZED ALLYLIC ACETOXYLATION, SIGMA-ORGANOPALLADIUM COMPLEXES, C-H OXIDATION, TERMINAL OLEFINS, ALKENES, ACIDS, FUNCTIONALIZATION, ACETATES, INSIGHTS, OXIDANT
  • Addresses:
    Sheppard, TD
    UCL
    Dept Chem
    Christopher Ingold Labs
    London
    WC1H 0AJ
    England
Abstract
The Pd-mediated oxidation of unsaturated thioacetals gives either allyl or vinyl esters, depending on the substrate structure. We report the characterization of a range of sulfur-stabilized palladium intermediates via a combined computational and experimental NMR approach, demonstrating that the oxidation proceeds via two divergent reaction mechanisms. We were also able to synthesize an unusual sigma-bound Pd complex, via acetoxypalladation of an unsaturated dithiane, which was characterized by X-ray crystallography.
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