Secondary phosphines are useful precursors to a variety of tertiary and multidentate phosphine ligands through hydrophosphination reactions as well as coupling reactions. While cross-coupling reactions have been shown to be useful tools in the synthesis of tertiary phosphines, there are few reports on the application of cross-coupling to the synthesis of secondary phosphines. Here, we report that in the presence of catalytic copper (I) iodide, supporting phosphine ligand and trimethylsilanolate base, we have observed cross-coupling between aryl iodides and phenylphosphine at 100 °C in pyridine over the course of 1h. These reactions proceed to high conversions, selectively producing secondary phosphines over tertiary phosphines. Secondary phosphine products may be isolated by chromatography with moderate to good yields.

Synthesis of secondary phosphines by copper-catalyzed P–C cross-coupling reaction

255th National Meeting (2018)

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