4.6 Article

Palladium-Catalyzed Alkoxycarbonylation of Terminal Alkenes To Produce α, β-Unsaturated Esters: The Key Role of Acetonitrile as a Ligand

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 16, Pages 4542-4547

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304798

Keywords

carbonylation; homogeneous catalysis; oxygen; palladium; solvent effects

Funding

  1. EPSRC [EP/E011179/1]
  2. Loughborough University
  3. Axel Wenner-Gren sabbatical scholarship
  4. COST through the ORCA action
  5. EPSRC [EP/E011179/1] Funding Source: UKRI
  6. Engineering and Physical Sciences Research Council [EP/E011179/1] Funding Source: researchfish

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A mild protocol has been developed for the Pd-II-catalyzed alkoxycarbonylation of terminal olefins to produce ,-unsaturated esters with a wide range of substrates. Key features are the use of MeCN as solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O-2, which facilitates the Cu-II-mediated reoxidation of the Pd-0 complex to Pd-II and prevents double carbonylation.

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