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Rollover in the synthesis of polycyclic indoles, and a one-pot Zipper-Click reaction
[Thesis]. Manchester, UK: The University of Manchester; 2016.
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Abstract
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.