4.8 Article

Palladium-catalyzed C-allylation of benzoins and an NHC-catalyzed three component coupling derived thereof: Compatibility of NHC- and Pd-catalysts

Journal

ORGANIC LETTERS
Volume 10, Issue 19, Pages 4243-4246

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801644f

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Funding

  1. the Deutsche Forschungsgemeinschaft
  2. the Funds der Chemischen Industrie
  3. the Deutscher Akademischer Austausch Dienst
  4. the Alfried Krupp von Bohlen and Halbach Foundation

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A large range of benzoins was successfully applied as C-nucleophiles in the palladium-catalyzed allylic alkylation with several allyl acetates, resulting in functionalized tertiary homoallylic alcohols. A number of unsymmetrical benzoins can be coupled with high levels of regio- and chemoselectivity. Finally, the challenging compatibility of free N-heterocyclic carbenes with a palladium catalyst has been utilized in a number of metal- and organocatalyzed three-component coupling reactions.

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