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Novel approaches to aromatic C–H borylation

Cross, Matthew; (2023) Novel approaches to aromatic C–H borylation. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

This thesis primarily explores novel approaches to C–H borylation in substrates containing (hetero)arenes. Chapter 1 provides an overview of the recent advances in aromatic C–H borylation, as well as free radical C–X borylation. Chapter 2 sets out our objectives for this research programme. Chapter 3.1 describes our attempts at performing the free radical borylation of aryl halides. The hypothesised protocol was to proceed via a base-free setup in the presence of an unsymmetrical diboron compound. Chapter 3.2 explores the limitations of iridium-catalysed borylation by screening an array of complex, ‘drug-like’ molecules. Our results give insight into the compatibility of various heterocycles and functional groups with this methodology, where previously unknown. The details of a study are reported into the regioselectivity observed when 4-substituted quinolines are subjected to standard iridium-catalysed borylation conditions. The investigation aimed to determine if the product regioisomer distribution is governed by the nature of the 4-substituent. Chapter 3.3 describes our attempts to devise a novel electrophilic borylation procedure mediated via the use of a late transition metal (Cu, Au). We report a simple and efficient method to transmetallate boron moieties (Bpin and Bdan) onto gold in high yields. A novel sp2-sp3 hybridised diboron compound is also reported (DIPA-dan diboron). However, its synthesis and isolation require optimisation in order to obtain sufficient quantities to probe reactivity. Chapter 3.4 reports a novel method to mono-N-methylate primary amines via the use of a halomethylboronate reagent. A boron-centred spiro compound was detected as a side product, thought to form via the activation of nitrile solvent. A series of novel structural analogues are reported, including an X-ray crystal structure.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Novel approaches to aromatic C–H borylation
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Copyright © The Author 2022. Original content in this thesis is licensed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) Licence (https://creativecommons.org/licenses/by-nc/4.0/). Any third-party copyright material present remains the property of its respective owner(s) and is licensed under its existing terms. Access may initially be restricted at the author’s request.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10164847
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