Exploring of new routes for rapid late-stage functionalization of BN-naphthalene cores

Author

Heras i Gil, Núria

Abstract

The inclusion of boron in organic molecules provides them with new and unique properties. In recent years, a trend in organic chemistry research has been the so-called BN/CC isosterism which consists in inserting a boron-nitrogen bond where there was initially a double bond between two carbon atoms. This isosterism represents a sophisticate strategy to include boron in different structures. Applying this strategy to arene compounds, such as polyaromatic hydrocarbons, supposes an enhancement of their properties that can have a positive effect on their optoelectronic performance, thus opening the door to new and more potent boron-doped organic functional materials. Also, due to the difference between its structure and that of the common aromatic hydrocarbons, this type of BN/CC isosterism could as well impact on the pharmacokinetic and pharmacodynamic profile of arene-containing drugs.
For all these reasons, the advances in synthetic methodologies applied to these interesting functional cores are especially welcome in the modern international scientific community.
Within this context, the project in which this TFG is framed, aims to combine the tremendous versatility of chemistry of hypervalent iodine species with the recently emerging area of the BN isosteric skeletons. Hence, an improved synthesis of a BN isostere of naphthalene, namely the 4a,8a-azaboranaphthalene, is carried out in a multigram scale. Once prepared, a series of highly versatile chemical methodologies (bromination, iodination, borylation and/or stannylation) are tackled in this study via both the classical and the more modern metal-catalyzed approaches to expand the available tools for a rapid complexity generation from the pre-formed boron–nitrogen (BN) heterocycles.
As a proof of concept of the viability of merging the high-valent iodine with a poly-aromatic BN isostere, the first hypervalent compound of this type has been generated in the form of an aryl/BN-heteroaryl λ3-iodonium salts, whose structure has been confirmed by NMR.

Director

Artalejo Ortega, Beatriz
Balfagón Costa, Alberto

Degree

IQS SE - Undergraduate Program in Chemistry

Date

2020-06-01