Dr Alison Stuart

Alison Stuart is a synthetic organic chemist who specialises in designing new fluorination procedures for drug discovery and chemical biology, and has >60 publications in organofluorine chemistry. She recently developed a new fluorinating reagent, fluoroiodane, which has been used to produce new fluorinated heterocycles and α-trifluoromethylated amines. These fluorinated compounds have crucial applications in pharmaceutical and agrochemical products, increasing their effectiveness, biological half-life and bioavailability.

An important strategy in the drug discovery process is the incorporation of fluorine because of its beneficial influence on the metabolic stability, lipophilicity and bioavailability of bioactive molecules. There are approximately 200 pharmaceuticals which contain fluorine and they cover all possible therapeutic areas. Furthermore, ¹⁹F NMR spectroscopy is a valuable tool for investigating biological processes. Since fluorine-containing natural products are extremely rare, access to these compounds relies on synthetic organic chemistry and my research is focused on designing new synthetic methodology for introducing fluorine into biologically-active molecules relevant for medicinal chemistry/drug development.  By studying the properties of a range of novel fluorinated motifs, I also aim to increase the range of fluorinated functional groups available for drug design.

In 2013 we introduced a hypervalent iodine(III) reagent as a new fluorinating reagent for installing carbon-fluorine bonds. The chelate sidearm makes it a stable, easy-to-handle solid. Fluorocyclisations of unsaturated carboxylic acids, oximes and hydrazones with our new reagent provided access to unprecedented fluorinated heterocycles with a high sp³ content. Heterocycles are normally contained within pharmaceutical products because of their biological activity in vivo, where their structure provides rigidity to molecular shape and enables effective binding to the active site. In drug design the αa-trifluoromethylamino group is used to improve the hydrolytic stability of drugs and in our most recent work, we have developed a selective and highly efficient method for preparing this fluorinated functional group by the late-stage, direct functionalisation of drug molecules with trifluoromethyl groups.

• B(C6F5)3-Catalysed coupling of N-alkyl arylamines and alkenes for the synthesis of tetrahydroquinolines, S. Moreen Gloria, L. Winfrey, Y. Gao, M. Barysevich, J. P. Gillions, L. Yun, H. Patel, A. Shah, A. Alvarez-Montoya, D. Thomas, A. Khan, H. Y. Harb, A. M. Stuart and A. P. Pulis, Org. Lett., 2025, 27, 9993.
• Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides, S. M. G. Dearman, X. Li, Y. Li, K. Singh and A. M. Stuart, Beilstein J. Org. Chem., 2024, 20, 1785-1793.
• Accessing novel fluorinated heterocycles with the hypervalent fluoroiodane reagent by solution and mechanochemical synthesis, W. Riley, A. Jones, K. Singh, D. L. Browne and A. M. Stuart, Chem. Commun., 2021, 57, 7406-7409.
• Fluorinations of unsymmetrical diaryliodonium salts containing ortho-sidearms; influence of sidearm on selectivity, A. M. H. Abudken, E. G. Hope, K. Singh and A. M. Stuart, Org. Biomol. Chem., 2020, 18, 6140-6146.
• Activation of the hypervalent fluoroiodane reagent by hydrogen bonding to hexafluoroisopropanol, H. K. Minhas, W. Riley, A. M. Stuart and M. Urbonaite, Org. Biomol. Chem., 2018, 16, 7170-7173.
• Intramolecular fluorocyclizations of unsaturated carboxylic acids with a stable hypervalent fluoroiodane reagent, G. C. Geary, E. G. Hope and A. M. Stuart, Angew. Chem. Int. Ed. Engl., 2015, 54, 14911-14914.
• Single-fluorophore detection in femtolitre droplets generated by flow focusing, R. Weinmeister, E. Freeman, I. C. Eperon, A. M. Stuart and A. J. Hudson, ACS Nano, 2015, 9, 9718-9730.
• Preparation of iodonium ylides: Probing the fluorination of 1,3-dicarbonyl compounds with a fluoroiodane, G. C. Geary, E. G. Hope, K. Singh and A. M. Stuart, RSC Adv., 2015, 5, 16501-16506.
• Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride, G. C. Geary, E. G. Hope, K. Singh and A. M. Stuart, Chem. Commun., 2013, 49, 9263-9265.

I am particularly interested in designing new synthetic methodology for the introduction of fluorine, trifluoromethyl and fluoroalkyl groups into biologically-active molecules.

Current research topics are:

1. Enantioselective fluorination
2. Late-stage functionalisation of amines with trifluoromethyl and difluoroalkyl groups
3. Designing new fluorinated motifs for drug discovery

I currently lecture in the following core organic courses at the University of Leicester: CH1201 Introductory Organic Chemistry and CH2201 Organic Chemistry. I also lecture at Dalian Institute of Technology: CH2201 Organic Chemistry and CH3201 Advanced Organic Chemistry.

Organofluorine chemistry and hypervalent iodine(III) chemistry

Royal Society University Research Fellow from October 2000 to April 2010

1. “A convenient oxidative fluorination procedure to form hypervalent iodine(V) fluorides”, 21st European Symposium on Fluorine Chemistry, Lisbon, Portugal, 3-8 August 2025.
2. “Teaching organic chemistry”, Online meeting with Dalian University of Technology and other Chinese Institutions, 18th June 2024.
3. “Fluoroiodane: A promising new fluorinating reagent”, Research Seminar at University of Nottingham, 7th February 2024.
4. “Fluoroiodane: A promising new fluorinating reagent”, Research Seminar at Durham University, 24th January 2024.
5. “Accessing novel fluorinated heterocycles with the hypervalent fluoroiodane reagent”, Research Seminar at Dalian University of Technology, Dalian, China, 20th October 2023.
6. “Accessing novel fluorinated heterocycles with the hypervalent fluoroiodane reagent”, Research Seminar at University of Bristol, 12th July 2023.
7. “Shaken and stirred: Fluorocyclisations by mechanochemical and solution synthesis”, 7th International Conference on Hypervalent Iodine Chemistry, Stockholm, Sweden, 25-28 June 2023.
8. “Intramolecular chloro- and fluoro-cyclisations of unsaturated oximes and hydrazones with hypervalent iodine(III) reagents”, 20th European Symposium on Fluorine Chemistry, Berlin, 14-19 August 2022.
9. “Accessing novel fluorinated heterocycles with the hypervalent fluoroiodane by solution and mechanochemical synthesis”, 50 in Abstracts of the 25th ACS Winter Fluorine Conference, Clearwater Beach, Florida, 16-21 January 2022.
10. “Fluorine and Iodine: A powerful combination for fluorination”, Research Seminar at Nottingham Trent University, 8th December 2021.
11. “Fluorine and Iodine: A powerful combination for fluorination”, Conference on Frontiers in Chemistry, REVA University, Bengaluru, India, 21-23 October 2021.
12. “Fluorine and Iodine: A powerful combination for fluorination”, Research Seminar at University of Reading, 16th March 2020.

BSc (St Andrews) PhD (Birmingham) Associate Fellow of the Higher Education Academy