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Title: Applications of DABSO in metal catalysis
Author: Richards-Taylor, Charlotte
ISNI:       0000 0004 5369 6072
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2014
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Chapter 1 discusses the importance of the sulfonyl moiety in biological compounds and the developments in the use of sulfur dioxide and sulfur dioxide donors in metal catalysis and organic synthesis. Chapter 2 focuses on the serendipitous discovery, optimisation and exploration of a route towards the synthesis of sulfones via an N-aminosulfonamide intermediate exploiting both palladium-catalysed aminosulfonylation and the predisposition of N aminosulfonamides to decompose to the sulfinate salt (Scheme 1). Scheme 1 Chapter 3 investigates the synthesis of benzosultams with an aryl-N-SO2 linkage. A range of benzosultams and its derivatives were prepared after optimisation of a synthetic sequence involving palladium-catalysed aminosulfonylation and a subsequent Buchwald– Hartwig coupling (Scheme 2). Scheme 2 Chapter 4 describes efforts towards the synthesis of a benzosultam with an aryl-SO2-N linkage through various precursors and metal-catalysed routes using DABSO as the sulfur dioxide source (Figure 1). Figure 1 Chapter 5 provides a summary of this thesis and outlines possibilities for future work. Chapter 6 provides experimental details and data for compounds discussed in this thesis. Appendix A details a brief investigation into the synthesis of N aminosulfonamides from heteroaryl iodides as an extension of the Willis group palladium-catalysed aminosulfonylation reaction (Scheme 3). Scheme 3 Appendix B presents 1H and 13C NMR spectra as well as X-ray crystallographic data of key compounds.
Supervisor: Willis, Michael Sponsor: Engineering and Physical Sciences Research Council ; Pfizer ; Lincoln College, Oxford
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic chemistry ; chemistry