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Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions

Hamed Goljani, Zahra Tavakkoli, Ali Sadatnabi, Davood Nematollahi

2020Organic Letters28 citationsDOI

Abstract

The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.

Topics & Concepts

ChemistryCopperElectrochemistryAnodeCatalysisInorganic chemistryPhase (matter)IonCombinatorial chemistryOrganic chemistryElectrodePhysical chemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsNanomaterials for catalytic reactions
Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions | Litcius