Synthesis of organoselenium compounds via flow electrochemistry

Alzaidi, Ohud 2024. Synthesis of organoselenium compounds via flow electrochemistry. PhD Thesis, Cardiff University. Item availability restricted.

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Abstract

Recently, Chemists have become interested in electroorganic chemistry because of its effectiveness and capacity to create organic compounds by introducing or withdrawing electrons. Furthermore, flow platforms are effectively used to provide practical solutions for the prevalent disadvantages of batch electrolysis. In this work, the focus will be on contributions of electroorganic synthesis especially of organselenium coumpounds, which have gained interest, recently, as reagents and catalysts due to their applications in medicinal and material sciences. Furthermore, another area of interest is the use of heterocyclic compounds containing selenium in organic conductors. The contributions of electroorganic synthesis to environmentally friendly chemistry will be the main focus of this work. In the first part of this work, the synthesis of novel non-racemic triazole-containing diselenides (Scheme i) was attempted via several routes. Chiral triazole-containing diselenides could not be synthesised with these concepts and further efforts would be required to achieve the synthesis and to attempt asymmetric selenenylations subsequently. A straightforward and effective electrochemical flow process has been developed for the αselenylation of 1,3-dicarbonyl compounds (Scheme ii) using a simple commercially available electrochemical flow cell (the Ion reactor). The main aim of this part is to develop an electrochemical methodology for the synthesis of α-selenyl derivatives of 1,3-dicarbonyl compounds and benefit from continuous flow electrochemical technology to efficiently access such highly valuable reagents that can be used in a wide range of chemical syntheses. Finally, for the electrochemical selenocyclization of N-allyl benzamides and unsaturated oximes to selenofunctionalized oxazolines and isoxazolines, respectively, a simple and effective continuous flow electrochemical method is established. Using a straightforward, widely accessible electrochemical flow cell (the Ion reactor), this process gives good yields of selenofunctionalized oxazolines and isoxazolines while working well with a wide variety of substrates (Scheme iii).

Item Type:	Thesis (PhD)
Date Type:	Completion
Status:	Unpublished
Schools:	Chemistry
Date of First Compliant Deposit:	27 January 2025
Last Modified:	27 Jan 2025 15:48
URI:	https://orca.cardiff.ac.uk/id/eprint/175586

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