4.8 Article

Room Temperature, Palladium-Mediated P-Arylation of Secondary Phosphine Oxides

Journal

ORGANIC LETTERS
Volume 14, Issue 17, Pages 4370-4373

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol301831k

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Funding

  1. David and Lucille Packard Foundation
  2. Searle Scholars Program
  3. Yale University

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We show that a broad range of aryl iodides are efficiently coupled with secondary phosphine oxides using 1 mol % of a catalyst formed in situ from tris(dibenzylideneacetone)dipalladium and Xantphos (1). Scalemic (S)-methylphenylphosphine oxide [(S)-2e] is shown to undergo arylation without detectable stereoerosion. The application of this method to the synthesis of novel P-chiral phosphines and PCP ligands is demonstrated.

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