Two Ph.D. student positions open from September 2017

1. Topic: Fluoroalkylated hypervalent iodine compounds for thiol bioconjugations

Abstract:
Fluorinated hypervalent iodine compounds such as Togni reagents have become widely used electrophilic trifluoromethylating reagents.¹ They display a unique reactivity profile and functional group compatibility. Recently, in our group we have prepared substituted tetrafluoroethylene-containing reagents and have shown their application in reactions with various nucleophiles.² In this project, we aim to synthetize fluoroalkylated hypervalent iodine reagents bearing a functional group and investigate their utilization in tagging biological thiols. New approaches to highly selective thiol bioconjugation are of great interest to biochemists.

Key references:
1. J. Charpentier, A. Togni, et al. Chem. Rev. 2015, 115, 650.
2. V. Matousek, P. Beier, et al. Chem. Eur. J. 2016, 22, 417.

2. Topic: Synthesis and reactivity of perfluoroalkyl azides and other N-perfluoroalkylated compounds

Abstract:
Organic azides are valuable intermediates in organic synthesis. We have recently reported efficient and scalable synthesis of CF₃N₃ and other perfluoroalkyl azides. Application of these useful but so far poorly studied fluorinated synthons in copper-catalyzed azide-alkyne cycloaddition provided novel N-perfluoroalkyl triazoles. In this project the rich chemistry of perfluoroalkyl azides will be investigated and new synthetic approaches to underdeveloped N-perfluoroalkyl-containing compounds will be studied. This class of compounds is expected to find utilization in drug discovery and in the development of new materials.

Key references:
1. Z. E. Blastik, P. Beier, et al. Angew. Chem. Int. Ed. doi: 10.1002/anie.201609715.
2. A. Budinská, P. Beier, et al. Org. Lett. 2016, 18, 5844.