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TFG_QU Santiago Abelleira, Danae.pdf (1.89 MB)

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Item embargoed until 2026-08-26

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Bachelor thesis

Publication date

2025-06

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cc-by-nc-nd (c) Santiago, 2025
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/222776

Visible-Light-Induced Functionalization of Oxindole Enol Ethers via EDA Complex Photoactivation

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Abstract

Light-mediated reactions offer a powerful platform for exploring chemical reactivity through controlled photoexcitation. This project focuses on advancing photoinduced reactions via electron donor-acceptor (EDA) complex activation, where interactions between an electron-rich donor and an electron-deficient acceptor generate reactive radicals under visible-light irradiation. Crucially, this approach operates without external catalysts—such as traditional metal-based photocatalysts—or sacrificial additives, enhancing synthetic efficiency. Central to our study is the functionalization of oxindoles, a privileged scaffold in medicinal chemistry due to the potent bioactivity of its derivatives. To achieve this, we designed and synthesized an oxindole-derived enol ether (donor 1) and paired it with Katritzky salts (acceptors 3 and 4) as complementary EDA complex partners. UV-visible spectroscopy confirmed EDA complex formation through the characteristic charge-transfer band (CT), while also identifying the optimal irradiation wavelength to maximize product formation and minimize byproduct generation. These findings establish a foundation for developing a mild, efficient, and catalyst-free methodology for oxindole functionalization. Future work will expand the scope of this reactivity and refine reaction conditions to enhance synthetic utility.

Description

Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2025, Tutor: Alberto Vega Peñaloza

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Fotoquímica, Llum visible, Treballs de fi de grau

Subject (English)

Photochemistry, Visible light, Bachelor's theses

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Treballs Finals de Grau (TFG) - Química

Citation

SANTIAGO ABELLEIRA, Danae. Visible-Light-Induced Functionalization of Oxindole Enol Ethers via EDA Complex Photoactivation. [consulted: 16 of August of 2026]. Available at: https://hdl.handle.net/2445/222776

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