Exploring Novel Silyl-Phosphonite Chemistry and New BioisosteresTools Wheeler, D F (2020) Exploring Novel Silyl-Phosphonite Chemistry and New Bioisosteres. PhD thesis, University of Nottingham.
AbstractPhosphinic acids are valuable synthetic targets which have many industrial applications. Most notably they have displayed biological activity as herbicides, and as pharmaceutical drugs for the treatment of a range of diseases. Herein, we report a novel P-C bond formation reaction for the synthesis of secondary phosphinic acids. This method is underpinned by the generation of a nucleophilic silylphosphonite intermediate via an unprecedented B(C6F5)3-catalysed silylation of primary phosphinic acids. A proposed mechanism for this transformation has been reported, and the scope of the reaction has been explored, with 20 secondary phosphinic acids being synthesised in 44 - 96% yield. Furthermore, the functionalisation of these phosphinic acids has allowed the synthesis of 8 Pstereogenic tertiary phosphine oxides. The outlined strategy constitutes a controlled route to tertiary phosphine oxides, which avoids PCl3 and other halophosphines.
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