Unsymmetric bisphosphines have been synthesized from secondary phosphine oxides (SPOs) as precursors. Traditional phosphine synthetic pathways typically require highly air- and water-sensitive starting materials. SPOs are advantageous as they are both air- and moisture-stable, allowing them to be used on the benchtop without sophisticated air-free techniques. Prepared SPOs were deprotonated with NaHMDS and added to excess 1-bromo-3-chloropropane. The resulting (3-chloropropyl)dialkylphosphine oxides were reacted with different deprotonated SPOs resulting in bis(phosphine) oxides (R2PO(CH2)3OPR’2, R, R’ = Me, Et, i-Pr, Ph, Cy, R ≠ R') which were then reduced to create the unsymmetric bisphosphines. These phosphines can be coordinated to metal ions as bidentate ligands, potentially creating “chiral-at-metal” complexes depending on metal ion geometry and stoichiometries. Future work will be focused on investigating the catalytic activity of the complexes.

Synthesis of unsymmetrical bisphosphines via secondary phosphine oxides precursors

ACS Spring Meeting 2021

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