Rhodium Catalysed Asymmetric Conjugate Addition to Alkenylheteroarenes / Continuous Flow Synthesis of 2-Trimethylsilyl arylperfluorosulfonates / Copper Catalysed Electrophilic Trifluoromethylation of Activated and Unactivated Alkyl Halides

  • Boris Michel

Student thesis: Phd


The first chapter of this thesis describes an investigation as a continuation of work published in 2010 on the asymmetric catalytic conjugate addition of aryl boronic acids onto alkenylazaarenes. The work described herein shows an attempt at facilitating asymmetric catalytic addition of alkenyl boronic acids to the same class of substrates. A number of novel chiral diene ligands were synthesised and investigated as well as a broad substrate scope subjected to the optimised reaction conditions. The second chapter contains the development of a flow chemistry process that enables the synthesis of 2-trimethylsilyl perfluorosulfonates in a very time and cost effective manner. Furthermore the utility of replacing triflic anhydride by nonaflyl fluoride as a sulfonating agent was investigated. The resulting benzyne pre-cursors were then subjected to a number of test reactions to show that they could be used with an equal versatility.The third and last chapter of this thesis demonstrates a new route to electrophilic trifluoromethylation of halogenated sp3-carbons via an active organozinc species in combination with Togni's reagent. An investigation into the applicability of this methodology across a broad substrate scope of commercially available alkyl halides was conducted.
Date of Award31 Dec 2016
Original languageEnglish
Awarding Institution
  • The University of Manchester
SupervisorMichael Greaney (Supervisor) & David Leigh (Supervisor)

Cite this