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Electrophilic aromatic substitution of azines catalysed by Frustrated Lewis pairs

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.

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MSCA-IF - Marie Skłodowska-Curie Individual Fellowships (IF)

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Call for proposal

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(opens in new window) H2020-MSCA-IF-2019

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Coordinator

FUNDACIO PRIVADA INSTITUT CATALA D'INVESTIGACIO QUIMICA
Net EU contribution

Net EU financial contribution. The sum of money that the participant receives, deducted by the EU contribution to its linked third party. It considers the distribution of the EU financial contribution between direct beneficiaries of the project and other types of participants, like third-party participants.

€ 172 932,48
Address
AVENIDA PAISSOS CATALANS 16
43007 TARRAGONA
Spain

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Region
Este Cataluña Tarragona
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Research Organisations
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Total cost

The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.

€ 172 932,48
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