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Archivio digitale delle tesi discusse presso l’Università di Pisa

Tesi etd-03142025-114311


Tipo di tesi
Tesi di dottorato di ricerca
Autore
ROSADONI, ELISABETTA
URN
etd-03142025-114311
Titolo
Novel protocols for the formation of carbon-carbon bonds on azoles via C-H functionalization
Settore scientifico disciplinare
CHEM-05/A - Chimica organica
Corso di studi
SCIENZE CHIMICHE E DEI MATERIALI
Relatori
tutor Prof. Bellina, Fabio
Parole chiave
  • azoles
  • C-H activation
  • C-H functionalization
  • catalysis
  • diazonium salts
  • direct alkylation
  • direct alkynilation
  • direct arylation
  • fluorophores
  • luminescent solar concentrators (LSC)
  • Minisci reaction
  • palladium-catalysis
Data inizio appello
31/03/2025
Consultabilità
Non consultabile
Data di rilascio
31/03/2028
Riassunto
This thesis discusses the development of new protocols for carbon-carbon bond formation on azoles via C-H functionalization. The main goal is the direct synthesis of C(sp2)-C(sp2) (direct arylation), C(sp2)-C(sp3) (direct alkylation), and C(sp2)-C(sp) (direct alkynylation) bonds, with applications in pharmaceuticals, materials science, and optoelectronics.
The research explores various catalytic and non-catalytic strategies, including palladium-catalyzed direct arylation of bioactive heterocycles and luminescent materials, as well as the use of eco-friendly solvents to improve reaction efficiency. A metal-free approach based on diazonium salts for imidazole arylation is also investigated. Additionally, a direct alkylation protocol is developed through a Minisci-type mechanism, utilizing carboxylic acids as green and cost-effective precursors. Finally, a previously established method for direct alkynylation is extended to the synthesis of fluorophores for luminescent solar concentrators.
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