This four-year Industrial CASE studentship on synthetic organic chemistry will be supervised by Dr Ai-Lan Lee in collaboration with AstraZeneca.
Background: The application of radical chemistry in synthesis has recently undergone a renaissance due to their powerful translational potential. Nevertheless, the generation of radicals is often associated with toxic, non-sustainable/expensive metals, photocatalysis, light, high temperatures or electrochemistry. This proposal builds on surprising observations in our lab that, contrary to the accepted convention, mild, decarboxylative C-H functionalisation of heterocycles does not require metal, photocatalyst, light, high temperatures nor electrolysis to proceed well.[2,3] A simple switch of solvent, followed by optimisation, successfully renders the C-H functionalisation of heterocycles metal-, catalyst-, light- and electrolysis-free! These sustainable and scalable conditions constitute a significant advance on cost, toxicity, waste and simplicity of operational procedure.
PhD Project: Following these exciting preliminary results, the aim of this collaborative PhD project is to extend our sustainable methodology to develop scalable, late-stage C-H functionalisations of pharmaceutically relevant heterocycles. In our proof-of-principle work, we predominantly based our optimisation studies on isoquinolines. In this PhD project, we will investigate the C H functionalisations of important classes of pharmaceutically relevant heterocycles, which were not the focus of our proof-of-principle study. Full optimisation and substrate scope studies will be carried out on the alkylation, acylation as well as carbamoylation reactions, and gram-scale reactions as well as late-stage C-H functionalisations will also be demonstrated to showcase the scalability and functional group tolerance.
Lee Group website: http://leegroup.eps.hw.ac.uk/
Informal enquiries should be directed to Dr Ai-Lan Lee: [email protected]
Formal applications should be made via Heriot-Watt University’s online application form: https://hwacuk.elluciancrmrecruit.com/Admissions/Pages/Login.aspx
When applying through the Heriot-Watt on-line system please ensure you provide the following information:
(a) in ‘Study Option’
You will need to select ‘Edinburgh’ and ‘Postgraduate Research’. ‘Programme’ presents you with a drop-down menu. Choose Chemistry PhD and select September 2020 for study option (this can be updated at a later date if required)
(b) in ‘Research Project Information’
You will be provided with a free text box for details of your research project. Enter Title and Reference number of the project for which you are applying and also enter the supervisor’s name. This information will greatly assist us in tracking your application.
Please note that once you have submitted your application, it will not be considered until you have uploaded your CV and transcripts.
 Yan, M.; Lo, J. C.; Edwards, J. T.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 12692.
 Sutherland, D. R.; Veguillas, M.; Oates, C. L.; Lee, A.-L. Org. Lett. 2018, 20, 6863.
 Westwood, M. T.; Lamb, C. J. C.; Sutherland, D. R.; Lee, A.-L. Org. Lett. 2019, 21, 7119.