Ahmed, Nehaal; (2023) Functionalisation of saturated heterocycles via aerobic C-H activation to form C-C bonds. Doctoral thesis (Ph.D), UCL (University College London).

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Abstract

This project is focused on the transformation of heterocycles by exploiting their interaction with oxygen in air as a means to construct C–C bonds via radical addition. Chapter one introduces fundamental information about radical reactivity, C–H bond transformations and aerobic C–H activation work. Furthermore, the reactions of radical acceptors used in this thesis are introduced alongside current methods for functionalising heterocycles. Chapter two describes the research and development section of this work, where an optimised reaction is developed for the C–C bond formation of heterocycles via an aerobic oxidation pathway. Alkynyl hypervalent iodine and acetylenic triflone radical acceptors are shown to be compatible with differing success in the designed reaction conditions. Following this, exemplification of the alkynylation reaction is demonstrated by reaction scope studies for both the heterocycles and radical acceptors. The method was also shown to be compatible with vinyl triflones allowing access to vinyl heterocycles in one step. The use of the products formed was demonstrated by novel transformations to generate privileged scaffolds and fundamental building blocks of varying oxidation levels. Mechanistic studies are carried out to confirm both the aerobic and radical nature of the developed reaction conditions. Future directions are also highlighted as a result of the findings in this thesis, finally the last chapter contains the experimental results and characterisations of compounds mentioned within the thesis.

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