APPLY LADDER OF CHEMICAL CIRCULARITY: RECYCLING OF RARE EARTH ELEMENTS RECOVERED FROM ELETRONIC WASTE AS A CATALYST IN ORGANIC REACTION.

This thesis investigates the application of lanthanide-based Lewis acids and copper catalysts in asymmetric and homogeneous catalysis, with a specific focus on continuous flow chemistry. The research extensively examines the Michael addition reaction between indoles and benzylidene malonates, employing these catalysts to achieve high reaction efficiency and selectivity. Additionally, a Diels-Alder cycloaddition was performed using chiral auxiliaries, promising results in terms of both reaction yield and enantioselectivity. The thesis also explores sustainable catalytic approaches by testing reactions using fluorescent lamps recovered from electronic waste (e-waste), achieving significant results in various catalytic environments, including homogeneous, heterogeneous, and continuous flow systems. During my period abroad in the group of Prof. C. Stevens at Ghent University, I further investigated the synthesis of aminotriazoles via a sequential Cu(I)-catalyzed dipolar cycloaddition (between azido pyridine and propiolate) followed by Cu(II)- catalysed C-H amination (through reaction with an amine), which resulted in satisfactory yields and selectivity. These results are reported in Chapter 5. The final part of the thesis is focused to the synthesis of Tezacaftor, focusing on an alternative and simplified synthetic protocol. Specifically, this study investigates the 5-endo cyclization of 2-(alkynyl)-anilines to indoles, a reaction traditionally known to proceed under Pd-catalysis but successfully carried out under Zn(II) catalyst. This approach offers a more accessible and potentially more sustainable route for the synthesis of this important pharmaceutical compound. The results are reported in Chapter 6.

Grantor dc:publisher

Università degli Studi di Milano

Year dc:date

2025

Author dc:creator

• DONATO, EMANUELA

Contributors dc:contributor

• tutor: M. Benaglia ; co-tutor: S. Rossi ; PhD coordinator: L. Prati
• E. Donato
• BENAGLIA, MAURIZIO
• PRATI, LAURA

• Settore CHEM-05/A - Chimica organica

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

eng

Identifier

http://dx.doi.org/10.13130/donato-emanuela_phd2025-01-20
10.13130/donato-emanuela_phd2025-01-20

OAI identifier oai:identifier

oai:air.unimi.it:2434/1135295