Laura Fra, PhD student under the supervision of Prof. Kilian Muñiz (ICIQ), has defended her PhD Thesis entitled
“New Applications of Iodine(III) Reactivity: Synthesis and Functionalization of Heterocycles” (assigned to the Organic and Analytical Chemistry Department of the Universitat Rovira i Virgili) publicly on September 22nd at the ICIQ Auditorium.
The members of the evaluation committee were: Prof. José Luis Mascareñas (Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares – CIQUS), Prof. Paolo Melchiorre (ICIQ) and Dr. Tanja Gulder (Universität München)
Two different methodologies have been developed for the synthesis of indoles using hypervalent iodine reactivity. First, a cyclization reaction has been proposed in which a total of 21 examples were obtained with good yields. In order to elucidate the reaction mechanism, different kinetic experimentes were performed such as the deuterium labellind technique. On the other hand, an alternative methodology has been performed with different starting materials obtaining a total of 18 examples in good yields through both a stoichiometric and catalytic transformation. The mechanism of the reaction has been studied by performing different mechanistic studies, such as the effect of the substituents of different electronic nature on one of the aromatic rings, through the Hammett correlation.
In addition to the application of hypervalent iodine compounds for the synthesis of heterocycles, their chiral derivatives have been used for the development of an enantioselective reaction for the 4-hydroxylation of phenols.