A deep eutectic solvent (DES) based on glycerol and KF is successfully exploited as a solvent medium in cross-coupling reactions between arenediazonium o-benzenedisulfonimides and organolithium reagents (Muharashi-Feringa coupling). The reactions were carried out in open air and in mild conditions. The target products were obtained in fairly good yield (15 examples; average yield: 60 %). This is, on the best of our knowledge, the first example of Muharashi-Feringa coupling carried out with diazonium salts. A tentative hypothesis of the reaction mechanism was also proposed.

Cross-Coupling Reactions between Arenediazonium o-Benzenedisulfonimides and Organolithium Reagents in a Deep Eutectic Solvent

Achille Antenucci
First
;
Stefano Dughera
2023-01-01

Abstract

A deep eutectic solvent (DES) based on glycerol and KF is successfully exploited as a solvent medium in cross-coupling reactions between arenediazonium o-benzenedisulfonimides and organolithium reagents (Muharashi-Feringa coupling). The reactions were carried out in open air and in mild conditions. The target products were obtained in fairly good yield (15 examples; average yield: 60 %). This is, on the best of our knowledge, the first example of Muharashi-Feringa coupling carried out with diazonium salts. A tentative hypothesis of the reaction mechanism was also proposed.
2023
8
e20230304
1
7
https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/slct.202303046?src=getftr
ArenediazoniumSalts, CrossCoupling, DeepEutecticSolvents, Muharashi-Feringacoupling, OrganolithiumReagents
Achille Antenucci; Stefano Dughera
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1933153
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