4.5 Article

SPANphos Ligands in Palladium-Catalyzed Asymmetric Fluorination

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 25, Pages 4844-4852

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200223

Keywords

Asymmetric catalysis; Ligand design; Palladium; Halogenation; Fluorine

Funding

  1. Spanish Ministerio de Ciencia e Innovacion (MICINN) [CTQ2005-03416, CTQ2008-00683]
  2. Consolider Ingenio Intecat [CSD2006-0003]

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The synthesis of new enantiopure wide-bite-angle diphosphanes is described as well as their use in the palladium-catalyzed asymmetric fluorination of a-cyanoacetates. Enantiomeric excesses up to 93?% were obtained when Pd(OAc)2-SPANphos was used as catalyst for the fluorination of ethyl 2-cyano-2-phenylacetate with N-fluorobenzenesulfonimide (NFSI).

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