Palladium-catalysed synthesis of sulfoxonium ylides



Janot, Christopher
(2019) Palladium-catalysed synthesis of sulfoxonium ylides. Doctor of Philosophy thesis, University of Liverpool.

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Abstract

The chemistry of stabilised sulfoxonium ylides in the presence of transition metals has gained in interest over the past few years because of their improved safety profile as compared to their diazo counterparts. However, no general method is available to access α-aryl disubstituted derivatives, limiting the scope of those reactions. This thesis highlights the work done towards the palladium-catalysed synthesis of α-aryl-α-carbonyl sulfoxonium ylides. It includes a thorough review of the literature related to the metal-catalysed reactions with stabilised sulfoxonium ylide in Chapter 1. Chapters 2 and 3 describe the arylation of α-ester and α-keto sulfoxonium ylides, respectively, as well as their use for the formation of C−N and C−S bonds. An experimental study of the mechanism for the reactions with the α-keto derivatives is also detailed demonstrating a different mechanism as compared to when the reaction is carried out with the diazo equivalents.

Item Type: Thesis (Doctor of Philosophy)
Divisions: Fac of Science & Engineering > School of Chemistry
Depositing User: Symplectic Admin
Date Deposited: 16 Jan 2020 10:50
Last Modified: 09 Jan 2021 02:41
DOI: 10.17638/03065751
Supervisors:
  • Aïssa, Christophe
URI: https://livrepository.liverpool.ac.uk/id/eprint/3065751