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New Strategies for the Synthesis of Hypervalent Iodine and Sulfur Compounds through Electrochemical Oxidation
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Orientador(es)
Resumo(s)
The significant challenges in organic chemistry can be viewed from two complementary perspectives. One involves the development of more environmentally friendly methods for synthesising target molecules, while the other focuses on the discovery of new pharmaceutical compounds for use in medicinal chemistry. In both contexts, organic electrosynthesis has emerged as a highly promising strategy, owing to its ability to oxidise molecules using electricity, thereby avoiding the hazardous and harmful redox reagents typically employed in traditional organic synthesis. In this work, we present two distinct projects focused on implementing electrochemical oxidation within more environmentally friendly processes. The first project concerns the site-selective late-stage deoxyfluorination of alcohols. This strategy involves the insertion of a thiol or disulfide moiety into complex molecules bearing multiple hydroxyl groups, which then act as precursors to fluorinating agents. These agents are generated electrochemically to produce sulfonyl fluoride species that can promote an intramolecular deoxyfluorination reaction, selectively targeting a proximal hydroxyl group. We successfully achieved the deoxyfluorination of a diol, obtained promising preliminary results with a triol, and synthesised a glucose derivative suitable as a substrate for the deoxyfluorination process. The second project involves the electrochemical synthesis of nitrogen-containing hypervalent iodine reagents, starting from a simple iodine (I) precursor. We successfully developed a streamlined, practical, and environmentally friendly one-pot electrochemical method to synthesise a benzylaminebenziodoxolone (BBX) compound from commercially available 2-iodobenzoic acid and benzylamine, achieving a 72% of yield.
Descrição
Tese de mestrado, Química (Química), 2025, Universidade de Lisboa, Faculdade de Ciências
Palavras-chave
Electrosynthesis late-stage deoxyfluorination sulfonyl fluoride hypervalent iodine