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Title: New methodologies for incorporation of nitrogen based functional groups onto carbon frameworks
Author: Rabet, Pauline
ISNI:       0000 0004 7658 0216
Awarding Body: University of Manchester
Current Institution: University of Manchester
Date of Award: 2018
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Nitrogen based functional groups are a recurrent motif in most natural products, pharmaceuticals and organic compounds in general. There is therefore a real interest in finding new, efficient and sustainable methodologies to install such functional groups onto carbon skeletons. Herein are presented several methodologies for the functionalisation of a number of substrates by new C-N bond formation. Using photoredox catalysis, the methoxy and di-azidation of styrenes and the benzylic azidation of tolyl substrates was achieved under mild conditions. These processes are notable for using a sustainable and cheap copper-based photoredox catalyst, as opposed to costly metal based complexes. Mechanistic investigations did not provide enough information to propose a definite mechanism for these transformations. Also reported are two strategies for amino arylation reactions. These metal-free functionalisations of internal alkynes, yielding tetra-substituted enaminones, and ketene, affording amides, proceed in good to excellent yields. This goes through a tandem addition/Truce-Smiles rearrangement reaction involving electron deficient sulfonamides under simple, user-friendly conditions.
Supervisor: Procter, David ; Greaney, Michael Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Nitrogen ; Catalyst ; Photoredox ; Rearrangement