Developing and Utilising Novel Sulphur Electrophiles as a new route to important Aryl-SF5 compounds

Fluorinated groups are ubiquitous in drugs with one particularly pervasive example being -CF3. Recently, the pentafluorosulfanyl group, -SF5, has attracted significant attention as an underexplored functional group in pharmaceutical products (see: ChemMedChem, 2017, 12, 1481). Aryl-SF5 moieties are stable under physiological conditions but have unique physical and chemical properties thus -SF5 groups are of significant interest, e.g. as a replacement for –CF3 in drug molecules. However, currently the utilisation of the –SF5 group in bioactives is limited by the significant challenge of installing it onto aromatics. Current routes often use highly hazardous F2 or require complex multistep approaches. This PhD. will focus on developing routes to functional equivalents of [SF5]+ for use in the SEAr of aromatic moieties to form Ar-SF5. One route to be explored will target activation of SF6, which is itself of import due to the significant global warming potential of SF6 (24,000 times more potent than CO2). In house fluoride ion affinity calculations have indicated a number of possible reagents that could activate SF6.

The Ingleson group works at the border between organic and inorganic chemistry and has extensive experience in synthesising and utilising novel main group electrophiles, this includes, aluminium, boron, carbon, silicon and phosphorus based electrophiles (for examples see: Angew. Chem. Int. Ed. 2018, 57, 10091, Chem. Sci., 2017, 8, 7969, Angew. Chem. Int. Ed., 2017, 56, 9202, Chem. Comm. 2018, 54, 12467). The group also has a track record of using main group electrophiles in electrophilic aromatic substitution to form useful products (for a recent example see: Angew. Chem. Int. Ed. 2019, 58, 15381, and highlight in C&EN). Thus the PhD. student will join a skilled team consisting of organic and organometallic chemists. The group currently consists of 4 PDRAs and 4 PhD. students.

The successful candidate will possess, or expect to obtain, a first class or upper-second class undergraduate degree (or equivalent) in chemistry. Essential qualities include a strong background in synthetic chemistry. In the first instance, informal enquiries (accompanied by a CV) should be directed to: Prof. Mike Ingleson Email: [Email Address Removed]

The position will remain open until filled and is available to start September 2020

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