Details

Autor(en) / Beteiligte

• Antenucci, Achille
• Bonomo, Matteo
• Ghigo, Giovanni
• Gontrani, Lorenzo
• Barolo, Claudia
• Dughera, Stefano

Titel

How do arenediazonium salts behave in deep eutectic solvents? A combined experimental and computational approach

Ist Teil von

• Journal of molecular liquids, 2021-10, Vol.339, p.116743, Article 116743

Ort / Verlag

Elsevier B.V

Erscheinungsjahr

2021

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• [Display omitted] •Synthesis of new DESs and DES–like systems based on polyols as HBDs and halide salts as HBAs.•Innovative DES design approach inspired by the necessity of rigorous classification of true DESs.•Unveiling of reduction process of diazonium salts in a new DES formed by glycerol and potassium fluoride.•Mechanistic study of the reduction process by DFT calculations and electrochemical measurements.•Combined theoretical and experimental approach promotes an unprecedented and successful insight on the chemistry of DESs. Despite the growing use of Deep Eutectic Solvents (DESs) as green reaction media in a number of organic syntheses, no significant reactions of diazonium salts in these solvents are known in the literature. In this paper, we present the behavior of arenediazonium tetrafluoroborates in new halide salts/polyol-based DESs, the nature of which is investigated by means of a combined computational and experimental approach. A relatively fast (strictly depending on the electronic effects of the substituents bound to the aromatic ring) reduction reaction occurs initiated by the formation of a glycerolate-like species as proved by a thorough computational study aiming at elucidating the involved mechanism.