AUPDCHARYL

Gold(I)-catalyzed decarboxylation in direct decarboxylative C-H arylation

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 Obiettivo del progetto (Objective)

'In the present research project we propose the development of new and innovative methodologies for organic synthesis, namely biaryl synthesis, by the combination of different metal-promoted processes. More specifically, the project will be built up on the very efficient procedure for gold-promoted decarboxylation of aromatic carboxylic acids, recently developed by the host group, giving place easily to arylgold(I) species. As we detail below, the transmetallation of these aryl units from gold to other metal (likely palladium) capable of performing an orthogonal transformation as C–H activation would allow the direct cross-coupling of (hetero)arenes (via C–H activation) and aromatic carboxylic acids (via C–CO2H activation, see Scheme 1) without any pre-functionalization. Such a methodology will significantly improve the current methodologies for the synthesis of biaryl motifs (ubiquitous in natural products, pharmaceuticals and organic materials) offering a more direct, economic and significantly greener approach. Replacing the use of organometallic compounds (frequently expensive, not trivial to prepare and giving place to large amounts of metal salt residues) by carboxylic acids (common functional groups in organic compounds, giving place to only CO2 as side product) will make cross-coupling processes more applicable both at laboratory and industrial scales and will very importantly reduce –virtually eliminate– their environmental impact.'

Introduzione (Teaser)

A recently completed EU project has developed a new method to connect two ring-shaped chemical compounds more cheaply and efficiently than the current method.

Descrizione progetto (Article)

Biaryl groups are created by connecting two circular chemical structures known as arenes, and are used in a wide range of pharmaceuticals, agrichemicals and electronics. Current methods use expensive reagents and have a high environmental impact due to waste products.

The EU-funded 'Gold(I)-catalyzed decarboxylation in direct decarboxylative C-H arylation' (AUPDCHARYL) project aimed to find new methods to produce biaryl compounds that do not require expensive starting materials and produce fewer toxic waste products.

The major finding from AUPDCHARYL was a proof-of-concept for a more sustainable method of biaryl production. This method uses gold atoms attached to the arene rings to catalyse the reaction.

Spurred by this initial success, researchers began experimenting with different conditions and a wide range of starting materials. By the end of the project, scientists had made progress in minimising waste products by optimising the reaction conditions.

AUPDCHARYL has taken steps towards a more efficient and environmentally friendly way to produce biaryl groups for chemical synthesis. This will have an immediate impact on research groups in the field, and a longer-term impact on the chemical manufacturing industry as a whole.