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Hydrogen-bonding ferrocene derivatives for molecular recognition and organocatalysis

Boissonnet, Michel-Franck (2015)
Ph.D. thesis, University of Birmingham.

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Abstract

The aim of this project was to prepare novel ferrocene-based Hydrogen-bonding receptors and to study them in the electrochemical sensing of neutral compounds and in organocatalysed transformations. The synthesis and characterisation of 2-ferrocenyl oxazoles via gold chemistry to access a new H-bonding motif for electrochemical sensing was successfully achieved. However the targeted structure bearing a secondary amine at the 4-position of the oxazole, was found to be highly unstable and unsuitable for sensing applications. Further studies on ferrocene-based H-bonding systems towards their application in asymmetric organocatalysis were also carried out. Different chiral and achiral ferrocene-(thio)ureas were prepared and tested in four organic reactions. Their performances in the Henry and in the Morita-Baylis-Hillman reactions gave acceptable yields but did not show significant enantioselectivities. A bi-functional ferrocene-thiourea was found to be effective in the enamine co-catalysed aldol reaction of acetone and \(trans-β\)-nitrostyrene, and in the double Michael cycloaddition of ω-nitropentenoate methyl and \(trans-β\)-nitrostyrene, leading to a tetrasubstituted cyclopentane. The H-bonding properties of the ferrocene-(thio)ureas with carboxylates was also studied by \(^1\)H NMR spectroscopy. Finally, approaches towards the preparation of ferrocene-based boronate-ureas were investigated.

Type of Work:Ph.D. thesis.
Supervisor(s):Tucker, James and Davies, Paul
School/Faculty:Colleges (2008 onwards) > College of Engineering & Physical Sciences
Department:School of Chemistry
Subjects:QD Chemistry
Institution:University of Birmingham
ID Code:6121
This unpublished thesis/dissertation is copyright of the author and/or third parties. The intellectual property rights of the author or third parties in respect of this work are as defined by The Copyright Designs and Patents Act 1988 or as modified by any successor legislation. Any use made of information contained in this thesis/dissertation must be in accordance with that legislation and must be properly acknowledged. Further distribution or reproduction in any format is prohibited without the permission of the copyright holder.
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