Isosterismo B/N: funcionalización tardía de BN-arenos mediante reacciones de sustitución electrófila aromática y aspectos sintéticos relacionados


Arruga Torres, Yolanda-Tomás


One of the lines of research in organic chemistry that has been booming in recent years is the synthesis of compounds that are or contain heteroarens, the so-called BN-isosters. These compounds are based on the substitution of a C = C double bond of the arenic ring by a B-N unit (boron-nitrogen). These advances have had a significant impact on the areas of pharmaceutical chemistry and materials science, which apply these BN-isostèrics arens in the development of new drugs and new materials with unique optoelectronic characteristics, among others.
In the first place, this work focuses on providing an overview of the electrophilic aromatic substitution type functionalization in different BN-arens (Naphthalene, Anthracene, Indole and phenanthrene), as well as explaining its mechanism and its intrinsic regioselectivity. BN-phenanthrene has been adopted as the structure of interest and the different synthetic strategies for the formation of the different isomers described in the bibliography have been compiled, together with the corresponding mechanistic analysis.
The second part of this work, already experimental, is based on the synthesis of 4a-aza-10a-borafenantrè, previously analyzed in the first part of this work, for its subsequent functionalization through electrophilic aromatic substitution reactions, specifically borylation. electrophilic. This part has been affected by the abrupt halt caused by the global CoV-SARS-2 virus pandemic. However, it has been possible to carry out the first synthesis step and to characterize the first intermediate spectroscopically.



Cuenca González, Ana Belén
Puig de la Bellacasa Cazorla, Raimon


IQS SE - Undergraduate Program in Chemistry