Seminar
22/07/2022
12:00
- Lecturer: Prof. Véronique Gouverneur
- University: University of Oxford (England)
Late-Stage fluorination with metal alkali fluoride
The invention of chemical reactions to create fluorine-containing molecules is an important aspect of modern medicine. Positron Emission Tomography (PET) with short-lived 18F-radiotracers is an imaging modality that can diagnose diseases, and monitor response to therapy. Moreover, the stable isotope 19F is commonly used in drug discovery to identify lead molecules and improve their properties. In this lecture, we will present our efforts towards asymmetric catalytic fluorination with metal alkali fluoride.
With the importance of chirality in chemistry, biology and drug discovery, we began our chemistry program with late stage stereoselective fluorination reactions of alkenes. With the current requirement to produce complex fluorochemicals more responsibly, this research evolved towards the invention of novel catalytic enantioselective carbon-fluorine bond forming processes using cost effective, safe and readily available alkali metal fluoride. This journey led us to explore at a fundamental level how one can harness and control fluoride reactivity. These studies paved the way to the discovery of a novel heterogeneous phase transfer catalysis manifold that we coined Hydrogen Bonding Phase Transfer Catalysis (HBPTC) and that we applied to potassium and cesium fluoride.[1] This chemistry inspired by the fluorinase enzyme[2] has enabled direct access to important fluorine-containing motifs for application in drug discovery.
References
[1] G. Pupo, F. Ibba, D. M. H. Ascough, A. C. Vicini, P. Ricci, K. E. Christensen, L. Pfeifer, J. R. Morphy, J. M. Brown, R. S. Paton, V. Gouverneur Science 2018, 360, 638.
[2] D. O’Hagan, C. Schaffrath, S. L. Cobb, J. T. G. Hamilton, C. D. Murphy Nature 2002, 416, 279.
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