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Professor Abigail Doyle Professor Veronique Gouverneur

One of the main research themes of the Gouverneur group is Fluorine Chemistry with an extensive research program aimed at developing novel synthetic methodologies for the preparation of fluorinated targets. Fluorine can be highly advantageous in pharmaceutical and agrochemical compounds as its presence can dramatically alter chemical and biological properties, including stability, lipophilicity and bioavailability. A recent survey has estimated that as many as 30-40% of agrochemicals and 20% of pharmaceuticals on the market contain fluorine, including half of the top drugs sold in 2005. As natural fluoroorganic compounds are extremely rare, major advances rely heavily on synthetic organic chemistry. In the group, we develop novel fluorine chemistry for the preparation of fine enantiopure fluorinated building blocks and drug-type targets. Our research programs are designed to build knowledge on how fluorinated stereogenic centers affect drug potency and other performance compounds.

A major spin-off avenue of research resulting from our activities is the preparation of [18F]-labeled radiopharmaceuticals suitable for Positron Emission Tomography (PET), a non-invasive diagnostic tool enabling the study of biochemical and physiological processes. With a half-life of circa 110 min [18F], it is critical to develop radiochemical methods featuring late introduction of the [18F] substituent within the tracer. This chemistry is designed with the aim of using PET to accelerate drug development.

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Pupo G, Vicini AC, Ascough DMH, Ibba F, Christensen KE, Thompson AL, Brown JM, Paton RS, Gouverneur V.
J Am Chem Soc. 2019 Feb 20;141(7):2878-2883. doi: 10.1021/jacs.8b12568. Epub 2019 Feb 4.
Potassium fluoride (KF) is an ideal reagent for fluorination because it is safe, easy to handle and low-cost. However, poor solubility in organic solvents coupled with limited strategies to control its reactivity has discouraged its use for asymmetric C-F bond formation...Read More
Pupo G#, Ibba F#, Ascough DMH#, Vicini AC, Ricci P, Christensen KE, Pfeifer L, Morphy JR, Brown JM, Paton RS, Gouverneur V.
Science. 2018 May 11;360(6389):638-642. doi: 10.1126/science.aar7941.
Common anionic nucleophiles such as those derived from inorganic salts have not been used for enantioselective catalysis because of their insolubility. Here, we report that merging hydrogen bonding and phase-transfer catalysis provides an effective mode of activation for nucleophiles that are insoluble in organic solvents...Read More
Pfeifer L, Gouverneur V.
Org Lett. 2018 Mar 16;20(6):1576-1579. doi: 10.1021/acs.orglett.8b00321. Epub 2018 Mar 1.
A novel protocol for the regio- and stereoselective iodofluorination of internal and terminal alkynes using 1,3-diiodo-5,5,-dimethylhydantoin and HF-based reagents is disclosed...Read More