Contacts:
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www.linkedin.com/in/elisabetta-rosadoni
Supervisor(s):
Prof. Fabio Bellina
Title of the PhD project:
C-H bonds activation of N-containing heterocycles
Abstract of the PhD project:
The development in recent decades of procedures for the direct functionalization of non-activated C-H bonds has created the possibility for medicinal chemistry to be able to increasingly use a synthetic strategy known as late-stage functionalization (LSF). In accordance with this strategy, C-H bonds are seen as functional groups and, therefore, as potential diversification points to generate new analogues from existing pharmaceutical leads, without having to resort to de novo synthetic procedures. As known, the main problem of the functionalization procedures of C-H bonds, in addition to the difficulties of reactivity related to the strength of these bonds, is represented by regioselectivity. In the context of LSF reactions, procedures involving C-H bonds of heterocycles have particular interest. In these cases, in fact, the presence of one or more heteroatoms grants a more marked differentiation of the different C-H bonds present, thus allowing an easier development of regioselective procedures.
Therefore, the propose of this PhD project will be aimed at identifying synthetic procedures for the selective functionalizing of N-containing heterocyclic systems, given their considerable importance as key structures in many biologically active compounds as well as in materials science, with particular attention to the development of procedure for the C(sp3)-H bonds functionalization.
Publications:
1. F. Bellina, M. La Manna and E. Rosadoni, “Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes”, Current Organic Chemistry 2021; 25. https://doi.org/10.2174/1385272825666210608115144
2. F. Bellina, M. Lessi, P. Ronchi, S. Guariento, M. Biagetti, M. Fausti and E- Rosadoni. “Ligand-free Pd/Ag-mediated dehydrogenative alkynylation of imidazole derivatives”, RSC Advances, 2021, 11, 25504-25509. https://doi.org/10.1039/D1RA05303E
3. E. Rosadoni, F. Bellina, M. Lessi, C. Micheletti, F. Ventura and A. Pucci, “Y-shaped alkynylimidazoles as effective push-pull fluorescent dyes for luminescent solar concentrators (LSCs)”, Dyes and Pigments, 2022; 201, 110262.
Oral communications at conferences:
1. F. Bellina, M. Biagetti, M. Fausti, G. Granucci, S. Guariento, M. Lessi, C. Micheletti, A. Pucci, P. Ronchi, E. Rosadoni, “Pd/Ag-mediated dehydrogenative alkynylation of imidazoles”. SCI 2021, XXVII National Congress of the Italian Chemical Society, September 14 - 23, 2021; oral communication.
Poster communications at conferences:
1. E. Rosadoni, M. Biagetti, M. Fausti, G. Granucci, S. Guariento, M. Lessi, C. Micheletti, A. Pucci, P. Ronchi, F. Bellina, “C-2 dehydrogenative alkynylation of imidazoles”. CFF 2021 - Chemistry for the Future International Conference, June 30 - July 2, 2021; poster and flash presentation.
2. F. Bellina, M. Lessi, P. Ronchi, S. Guariento, M. Biagetti, M. Fausti and E. Rosadoni. “Ligand-free dehydrogenative alkynylation of imidazoles”. ESOC 2021, European Symposium on Organic Chemistry Virtual Mini Symposium, July 5 - 6, 2021; poster.
Other achievements:
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