An electrochemical nickel-catalyzed arylation of 3-amino-6-chloropyridazines.

J Org Chem

Equipe Electrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris-Est, UMR 7182 CNRS-Université Paris-Est Créteil Val de Marne, 2 rue Henri Dunant, BP 28, F-94320, Thiais, France.

Published: January 2013

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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http://dx.doi.org/10.1021/jo3022428DOI Listing

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