Visible-Light Mediated C–H Functionalisation of Unprotected Primary Amines

  • George Ballantyne

Student thesis: Masters ThesisMPhil

Abstract

New methods for the C−H functionalisation of aliphatic primary amines using dual photoredox
and hydrogen-atom-transfer (HAT) catalysis have been investigated herein.
Chapter 1 provides an overview of the importance of aliphatic amines in organic synthesis,
including current methods for the α-C-functionalization of primary amines to access α-tertiary
amine scaffolds. The fundamental principles and synthetic applications of photoredox catalysis
are also discussed.
Chapter 2 presents the development of a previously optimised C−H alkylation reaction of
unprotected primary amines, including examples from a substrate scope for this process.
Optimisation of the first example of tandem C−H and N-functionalisation from primary amines
is also reported using N-electrophiles to access α-functionalised secondary amines, scaffolds
of high value in medicinal chemistry.
Chapter 3 showcases the optimisation studies for a novel C−H heteroarylation reaction of
unprotected primary amines with 2-chloro-thiazole derivatives to access α-amino thiazoyls
through a radical SNAr process. A substrate scope for this process for both the amine and arene
coupling partners is also included.
Future work for the heteroarylation project (Chapter 4) is also discussed, including potential
applications in continuous flow.
Chapter 5 describes the experimental procedures used in Chapters 2 and 3, including full
characterisation of all samples prepared.
Date of Award16 Jun 2020
Original languageEnglish
Awarding Institution
  • University of Bath
SupervisorAlex Cresswell (Supervisor) & Steven Bull (Supervisor)

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