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MO: Fachverband Molekülphysik
MO 6: Poster I
MO 6.2: Poster
Tuesday, March 7, 2023, 16:30–19:00, Empore Lichthof
Time-resolved study of the photogeneration of the phenylselenium cation from diphenyl diselenide and subsequent use for covalent activation in organic reactions — •Daniel Grenda1, Anna Tiefel2, Carina Allacher1, Alexander Breder2, and Patrick Nürnberger1 — 1Institute of Physical and Theoretical Chemistry, University of Regensburg, Regensburg — 2Institute of Organic Chemistry, University of Regensburg, Regensburg
Using a pump-probe setup on a µs-timescale with a streak-camera detector [1], one can investigate light-induced chemical reactions with long-lived intermediates. We apply this technique to organoselenium compounds, which are useful catalysts in organic synthesis due to their stability towards oxygen and their rich radical chemistry [2]. Especially diphenyl diselenide is a versatile precursor for organic synthesis, as it is often used to generate phenylselenyl radicals by photolytic cleavage of the selenium-selenium bond [3]. However, we demonstrate that given the right reaction conditions, the phenylselenium cation can be generated in a similar way, which then is utilizable for covalent activation of allylic selenium species [4].
[1] R. J. Kutta et al., Appl. Phys. B 111, 203-216 (2013).
[2] A. Breder et al., Tetrahedron Lett. 56, 2843-2852 (2015).
[3] O. Ito et al., J. Am. Chem. Soc., 105, 850-853 (1983).
[4] M. Tingoli et al., J. Org. Chem. 61, 7085-7091 (1996).