Project description
A novel catalytic process simplifies selective production of important aromatic molecules
Synthetic chemistry faces numerous reaction barriers to what is actually possible compared to what is theoretically possible. Catalysts are critically important to overcoming many of these barriers by reducing the energy required for a reaction to proceed, often enabling a substitution or functionalisation of simple feedstocks that can lead to high value products. Aromatic substitution, typically the replacement of a hydrogen in an aromatic ring by another moiety, is an important chemical reaction. The aromatic substitution of azines, nitrogen-containing aromatic rings, is relevant to numerous fields, yet the reactions require very complicated conditions to proceed. The EU-funded LEWIS-PYR project is developing a highly selective catalytic process to enable the electrophilic aromatic substitution of azines with mild reaction conditions, opening the door to innovation in fields from pharmaceuticals to materials science.
Objective
Azines are nitrogen-containing aromatic rings of utmost synthetic relevance in natural products, pharmaceuticals, agrochemicals and materials science. Although nucleophilic aromatic substitution techniques are routine, these methods require air-sensitive and highly reactive nucleophiles, in most instances organometallic reagents. In sharp contrast, electrophilic aromatic substitutions are particularly difficult to the electron-poor nature of the azines, inevitably requiring harsh reaction conditions. Taking into consideration the wider availability of electrophilic partners when compared to their corresponding nucleophilic congerener, the development of a catalytic technique aimed at providing a mild, chemoselective and site-selective electrophilic aromatic substitution of azines will have tremendous consequences for the praxis of heterocyclic chemistry, particularly in late-stage applications. Aimed at providing a solution to such goal, LEWIS-PYR will design a conceptually new platform to activate unbiased azines via electrophilic aromatic substitution by using frustrated Lewis Pairs (FLPs) as a polarity inversion vehicles, allowing to substitute a series of a priori electron-poor nitrogen-containing electrocycles with a wide variety of different electrophilic partners.
Fields of science
Programme(s)
Funding Scheme
MSCA-IF - Marie Skłodowska-Curie Individual Fellowships (IF)Coordinator
43007 Tarragona
Spain