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Title: Rollover in the synthesis of polycyclic indoles, and a one-pot Zipper-Click reaction
Author: Balgobin, Sinead
ISNI:       0000 0004 7225 2194
Awarding Body: University of Manchester
Current Institution: University of Manchester
Date of Award: 2016
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This thesis contains two chapters, the first concerning the use of C-H activation in the synthesis of polyaromatic indoles, and the second concerning an investigation into the acetylene zipper reaction. C-H activation provides a convenient, atom efficient route for the construction of C-C bonds, without the prerequisite for stoichiometric organometallic precursors or pre-functionalisation of the substrates. In this research the use of C-H activation for the insertion of an alkyne into an N-(hetero)arylated indole system has been investigated; the transformation was achieved using Rh catalysis in moderate to good yields. The concept of rollover has also been discussed. This is where, after a metallation step, the molecule undergoes a bond rotation allowing further reaction at a different part of the molecule. The acetylene zipper reaction is a powerful contrathermodynamic reaction which allows the migration of an internal alkyne to the terminal position. The alkyne moiety is a useful handle for many reactions, not least the robust CuI-catalysed azide alkyne cycloaddition (CuAAC, also known as a click reaction), which can be used to synthesis useful triazole products. In this research a one-pot zipper-click reaction has been investigated to provide 1,4-disubstituted-1,2,3-triazoles.
Supervisor: Quayle, Peter ; Greaney, Michael Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available