Room temperature, palladium-mediated P-arylation of secondary phosphine oxides

Org Lett. 2012 Sep 7;14(17):4370-3. doi: 10.1021/ol301831k. Epub 2012 Aug 20.

Abstract

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.