Exploring Novel Silyl-Phosphonite Chemistry and New Bioisosteres

Wheeler, D F

Exploring Novel Silyl-Phosphonite Chemistry and New Bioisosteres

Publication Date

July 24, 2020

Creator

Wheeler, D F

Abstract

Phosphinic 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.

Item Type

ethesis

Thesis Type

PhD

Supervisors

Denton, Ross

Shanahan, Stephen

Burton, Paul

Keywords

Phosphinic acids

organometallics

Subjects (LC)

QD Chemistry::QD241 O...

Associated Schools / Departments

School of Chemistry

eprints ID

59944

UoN Repository URI

https://repository.nottingham.ac.uk/handle/123456789/63553

Except where otherwise noted, this item's license is described as

https://copyrightalliance.org/faqs/what-is-all-rights-reserved/

Name

Exploring Novel Silyl-Phosphonite Chemistry and New Bioisosteres - Part 1.pdf

Type

Full-text

Description

Examined

Size

3.67 MB

Format

Adobe PDF

Checksum (MD5)

da2bdd5f3f255b8b58d346bd085fd334

Name

Exploring Novel Silyl-Phosphonite Chemistry and New Bioisosteres - Part 2.pdf