A variety of unsymmetric bisphosphines have been synthesized from secondary phosphine oxides as starting materials. Traditional phosphines are very pyrophoric, and most synthetic pathways require highly air- and water-sensitive starting materials. Secondary phosphine oxides are advantageous as they are both air and moisture stable, making them much easier to work with. The synthesized secondary phosphine oxides were deprotonated with NaHMDS and added to excess 1-bromo-3-chloropropane. The resulting (3-chloropropyl)dialkylphosphine oxides were reacted with different deprotonated secondary phosphine oxides. This resulted 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 a bidentate ligand creating a “chiral-at-metal” complex. Future work will be focused on separating the resulting complexes with the previously synthesized ��-TRISPHAT anion. Upon separation, the catalytic properties can be tested and compared to more traditional catalysts.

Toward chiral-at-metal complexes via unsymmetrical bisphosphine oxides

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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