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Hypervalent Iodine(V) Reagents: A New Strategy for Fluorination

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  • Full or part time
    Dr A Stuart
    Dr A Pulis
  • Application Deadline
    No more applications being accepted
  • Competition Funded PhD Project (European/UK Students Only)
    Competition Funded PhD Project (European/UK Students Only)

Project Description

Fluorinated molecules play a pivotal role in the development of new pharmaceutical and agrochemical products because the incorporation of fluorine can increase their effectiveness, biological half-life and bioavailability. There are approximately 200 current pharmaceuticals that contain fluorine, and 30% of the top 30 drugs contain at least one fluorine atom. Consequently, there is a huge demand from industry for more efficient methods for introducing fluorine into a wide range of compounds, particularly methods that use nucleophilic fluorination with a benign source of fluoride ion, as opposed to potentially hazardous electrophilic fluorinating reagents.

The desire for new methods of fluorination is also fuelled by the rapidly growing, non-invasive medical imaging technique of positron emission tomography (PET), a powerful method that allows quantification of biochemical processes in vivo, widely used in oncology for diagnosis, staging and management of patients, accurate treatment planning and monitoring the response to therapy. Due to its favourable physical properties (β+ 0.635 MeV, t½ 109.7 min), fluorine-18 (18F) is often the radionuclide of choice for PET imaging. Most PET laboratories are only able to produce the radionuclide as [18F]fluoride and so, most applications of PET chemistry are limited to 18F-radiotracers that can be readily prepared by conventional nucleophilic substitutions. Therefore, it is highly desirable to develop new methodologies that employ nucleophilic fluoride sources.

The aim of this research is to:
• Synthesise a new class of hypervalent iodine(V) reagents (Figure 1) and investigate their potential to react like classic electrophilic fluorinating reagents with a range of nucleophilic substrates such as Grignard reagents, 1,3-dicarbonyl substrates and alkenes.
• Develop a new synthetic route to the hypervalent iodine(V) reagents by reacting the chlorinated analogues with nucleophilic fluoride sources (KF, TBAF) because fluoride is attractive in terms of cost for the pharmaceutical industry and is required for the preparation of 18F-labelled radiotracers for medical diagnostics.

Entry requirements

Applicants are required to hold/or expect to obtain a UK Bachelor Degree 2:1 or better in a relevant subject. The University of Leicester English language requirements apply where applicable.

How to apply

The online application and supporting documents are due by Thursday 25th April 2019.

Any applications submitted after the deadline will not be accepted for the studentship scheme.

References should arrive no later than Monday 29th April 2019.

Applicants are advised to apply well in advance of the deadline, so that we can let you know if anything is missing from your application.

Required Materials
1. Online application form
2. Two academic references
3. Transcripts
4. Degree certificate/s (if awarded)
5. Curriculum Vitae
6. English language qualification

Applications which are not complete by the deadline will not be considered for the studentship scheme. It is the responsibility of the applicant to ensure the application form and documents are received by the relevant deadlines.

All applications must be submitted online, along with the supporting documents as per the instructions on the website.
Please ensure that all email addresses, for yourself and your referees, are correct on the application form.

Project / Funding Enquiries

Application enquiries to [Email Address Removed]
Closing date for applications – 25th April 2019

Funding Notes

This research project is one of a number of projects in the Department. It is in competition for funding with one or more of these projects. Usually the project which receives the best applicant will be awarded the funding.

Home/EU Applicants

This project is eligible for a fully funded Graduate Teaching Assistant studentship which includes :

• A full UK/EU fee waiver for 4 years
• A stipend/salary package at UKRI rates

International Applicants

This project does not have any funding for international students.

References

1. H. K. Minhas, W. Riley, A. M. Stuart, M. Urbonaite, Org. Biomol. Chem., 2018, 16, 7170.
2. G. C. Geary, E. G. Hope, A. M. Stuart, Angew. Chem. Int. Ed. Engl., 2015, 54, 14911.
3. R. L. Amey, J. C. Martin, J. Am. Chem. Soc., 1979, 101, 5294.



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