An Electrochemical Nickel-Catalyzed Arylation of 3-Amino-6-Chloropyridazines
The Journal of Organic Chemistry2012Vol. 78(2), pp. 370–379
Citations Over TimeTop 19% of 2012 papers
Stéphane Sengmany, Arnaud Vitu‐Thiebaud, Erwan Le Gall, Sylvie Condon, Éric Léonel, Christine Thobie‐Gautier, Muriel Pipelier, Jacques Lebreton, Didier Dubreuil
Abstract
3-Amino-6-aryl- and 3-amino-6-heteroarylpyridazines have been obtained in generally good yield using a nickel-catalyzed electrochemical cross-coupling between 3-amino-6-chloropyridazines and aryl or heteroaryl halides at room temperature. Comparative experiments involving classical palladium-catalyzed reactions, such as Suzuki, Stille, or Negishi cross-couplings, reveal that the electrochemical method can constitute a reliable alternative tool for biaryl formation. A possible reaction mechanism is proposed on the basis of electrochemical analyses.
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