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Synthesis of Novel Cubane Scaffolds

Synthesis of Novel Cubane Scaffolds
Synthesis of Novel Cubane Scaffolds
First synthesised in the 1960s and originally proposed as 3D benzene bioisostere in the 1990s, cubane scaffolds have gained real interest in medicinal chemistry the past decade. Substituting a phenyl ring by a cubyl unit could lead to improved physical and biological properties. Moreover, cubanes have find interest as non–aromatic rigid spacers in organic materials and polymers. However, the geometric requirements of cubane are far from ordinary, therefore, accessing cubane motifs is still hampered by non–trivial synthetic access. With the growing awareness concerning hazardous chemicals and waste generated from synthetic chemistry, there has been a drive to re-evaluate the way organic chemistry is conducted. In some cases, processing chemical reactions in microreactors under a continuous–flow manner has shown to be particularly efficient. In addition, the use of light or electricity has been considered as sustainable methodology in order to replace potentially hazardous/toxic and costly chemical reagents. This thesis aims to the development and optimisation of synthetic routes using flow photochemistry and electrochemistry in order to generate new cubane scaffolds.
University of Southampton
Collin, Diego, Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Collin, Diego, Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Collin, Diego, Edgard (2022) Synthesis of Novel Cubane Scaffolds. University of Southampton, Doctoral Thesis, 175pp.

Record type: Thesis (Doctoral)

Abstract

First synthesised in the 1960s and originally proposed as 3D benzene bioisostere in the 1990s, cubane scaffolds have gained real interest in medicinal chemistry the past decade. Substituting a phenyl ring by a cubyl unit could lead to improved physical and biological properties. Moreover, cubanes have find interest as non–aromatic rigid spacers in organic materials and polymers. However, the geometric requirements of cubane are far from ordinary, therefore, accessing cubane motifs is still hampered by non–trivial synthetic access. With the growing awareness concerning hazardous chemicals and waste generated from synthetic chemistry, there has been a drive to re-evaluate the way organic chemistry is conducted. In some cases, processing chemical reactions in microreactors under a continuous–flow manner has shown to be particularly efficient. In addition, the use of light or electricity has been considered as sustainable methodology in order to replace potentially hazardous/toxic and costly chemical reagents. This thesis aims to the development and optimisation of synthetic routes using flow photochemistry and electrochemistry in order to generate new cubane scaffolds.

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More information

Submitted date: September 2021
Published date: 2022

Identifiers

Local EPrints ID: 456886
URI: http://eprints.soton.ac.uk/id/eprint/456886
PURE UUID: 1607a0d4-b921-4fba-8f95-9beb32244024
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 16 May 2022 16:31
Last modified: 23 Jul 2022 01:47

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Contributors

Author: Diego, Edgard Collin
Thesis advisor: Bruno Linclau ORCID iD

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