Obhajoba DSc. v organické chemii – Petr Beier

Organic azides are widely used compounds in synthesis and also in biochemistry. α-Fluorinated azidoalkanes are a subgroup which has been regarded as a chemical curiosity and their chemistry has not been developed. In this work, we showed the synthetic access to a variety of fluorinated organic azides from CF₃N₃ to more elaborated ones and studied the factors influencing their stability, which opened up new possibilities for their application in organic synthesis. A photocatalytic nitrene formation gave access to nitrene reactive intermediates, useful in the synthesis of N-trifluoromethyl aziridines. [3+2] cycloaddition reactions of fluorinated azides afforded N-fluoroalkylated 1,2,3-triazoles. A study of denitrogenative processes of those triazoles allowed the preparation of a variety of structurally diverse nitrogen heterocycles and N-alkenyl compounds. A majority of those products showed a synthetic potential in follow-up derivatization reactions or resemble molecules used in the drug design. Yet unreported are reactions of fluorinated azides with nucleophiles, new reactivity of nitrenes, or metal-free cycloaddition for chemical biology applications. All of these research directions are being investigated in our laboratory.

The full text of DSc dissertation is available from the chairman of the committee Prof. Michal Hocek upon request.