An Improved Route for the Synthesis of Phosphine Oxides Via the Alkylation of Phosphonates Through the Use of Grignard Reagents and Halide Scavengers

Presenter: Chase Salazar

Mentor: David Tyler

Oral Presentation

Major: Chemistry

An added improvement to the low-yielding reaction of phosphonates to phosphine oxides is shown. The use of a halide scavenger will increase the yield of the phosphonates to phosphine oxides alkylation from 20% to up to 95% yields by preventing a side reaction that is suggested to be caused by halides from the Grignard reagents. The large scope of substrates and excellent yields of the reaction makes it a pragmatic method for phosphine oxide synthesis as compared to the current method that requires harsh chlorination conditions with low yields. This high yielding adaptation to the alkylation of phosphonates to phosphine oxides offers a new synthetic route to the synthesis of asymmetric tertiary phosphines. Phosphines are highly used for coupling reactions in the manufacturing of pharmaceuticals and other specialty chemicals. This new proposed route is performed with bench top chemistry that has equal or higher yields to the current phosphine ligand synthesis that requires strict air-free chemistry techniques and hazardous work with pyrophoric materials. The new method allows for a simpler and safer synthetic route for phosphine ligand synthesis.

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