Synthesis of Novel Cubane Scaffolds

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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ORCID for Bruno Linclau: orcid.org/0000-0001-8762-0170

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