Synfacts 2008(5): 0521-0521  
DOI: 10.1055/s-2008-1072520
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Coupling of Hydroxylamines with Aryl Iodides

Contributor(s): Paul Knochel, Andrei Gavryushin
K. L. Jones, A. Porzelle, A. Hall, M. D. Woodrow, N. C. O. Tomkinson*
Cardiff University and GlaxoSmithKline, UK
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Publikationsverlauf

Publikationsdatum:
23. April 2008 (online)

Significance

Copper-catalyzed modified Ulmann condensation is now one of the best ways for the preparation of arenes bearing nitrogen-containing substituents. This is the first report of a Cu-catalyzed N-arylation of hydroxylamines. N-Arylhydroxylamines are extremely valuable intermediates for the synthesis of various nitrogen-containing compounds of use for the preparation of pharmaceutical agents. This method allows an easy synthesis of orthogonally protected N-arylhydroxyl­amines, opening direct ways for their further functionalization.