Project Summary
Background: C-H functionalisation is the most efficient way to generate value added products, and C-H borylation is one of the most common approaches used in this area. Borylation (formation of C-B bonds) chemistry is pervasive in academia and industry due to the synthetic utility of boronic acid derivatives. However, selectively functionalising certain C-H bonds on a (hetero)arene remains a significant challenge due to the intrinsic properties of the heteroarene. So how would you direct reactivity to a C-H that is inherently less reactive? Most approaches focus on the use of rare and toxic transition metal based catalysts (e.g. iridium) and complex directing groups which is not only unsustainable but also tends to be highly step inefficient. Our team, however, has been tackling this issue with an alternative approach – without metals and the need for installing directing groups altogether!
The project: The Ingleson group have recently disclosed a completely new metal and directing group free approach in this area (see references below) using compounds that have two electrophilic boron centres in one molecule (termed diboron electrophiles). In our proof of principle publication titled “borylation directed borylation” these compounds enabled selective C-H functionalisation at an unusual position in important heteroarenes, such as indole and indoline. This PhD. will join a team focused on taking this approach forward, e.g. by designing new diboron electrophiles and targeting novel C-H functionalisations of relevance to the pharmaceutical and materials sectors. Possible targets include directing group/metal free selective meta C-H borylation of arenes and selective beta borylation of heterocycles such as thiophenes. We would also look to extend this approach to hydroboration directed borylation to target C-H borylation of other heterocycles (e.g. pyridines).
This is a synthetic chemistry project at the border of organic and inorganic chemistry. Should you undertake this project, you will receive training in a wide variety of techniques and synthesise a wide range of main-group and organic compounds, frequently under inert atmosphere. Multinuclear NMR, mass spectrometry and X-ray crystallography will be central techniques. If the candidate wishes, the project can have a significant organic materials element to it (organoboron compounds are becoming vital as metal free efficient emitters in OLED), and this would lead to training in optoelectronic characterisation techniques. The extensive practical skills you will gain will be complemented by scientific problem solving and presentation skills that you will develop in regular group meetings and by interacting with friendly and diverse colleagues in the Ingleson group and the wider School of Chemistry. You will have opportunities to present your work at suitable national and/or international conferences.
You should possess a recent chemistry degree (first class or 2(i), or equivalent). You will need to demonstrate a strong interest in synthetic chemistry. You should have some experience of organic or inorganic synthesis (or a closely related area), and excellent written and oral communication skills.
Application Process
In the first instance, the initial application (including cover letter and CV) should be directed to: Prof. Mike Ingleson, School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh EH9 3FJ, UK. Email: [Email Address Removed]
The position will remain open until filled.
IMPORTANT
Before Submitting your cover letter and CV, please complete the online School of Chemistry Equality, Diversity & Inclusion Form 2023. The form will automatically generate a unique “Receipt Number” that you MUST include in your cover letter.
Equality and Diversity
The School of Chemistry holds a Silver Athena SWAN award in recognition of our commitment to advance gender equality in higher education. The University is a member of the Race Equality Charter and is a Stonewall Scotland Diversity Champion, actively promoting LGBT equality. The University has a range of initiatives to support a family friendly working environment. See our University Initiatives website for further information. University Initiatives website: https://www.ed.ac.uk/equality-diversity/help-advice/family-friendly
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