Palladium-Catalyzed Coupling of Hydroxylamines with Aryl Bromides, Chlorides, and Iodides

Achim Porzelle, Michael D. Woodrow and Nicholas C. O. Tomkinson*

*School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, United Kingdom, Email: tomkinsonnccardiff.ac.uk

A. Porzelle, M. D. Woodrow, N. C. O. Tomkinson, Org. Lett., 2009, 11, 233-236.

DOI: 10.1021/ol8025022

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Abstract

The bis-pyrazole phosphine BippyPhos is an effective ligand for a smooth palladium-catalyzed cross-coupling of hydroxylamines with aryl bromides, chlorides, and iodides at 80°C in toluene in the presence of Cs₂CO₃ to give synthetically versatile N-arylhydroxylamine products in good to excellent yield.

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Copper-Catalyzed Coupling of Hydroxylamines with Aryl Iodides

K. L. Jones, A. Porzelle, A. Hall, M. D. Woodrow, N. C. O. Tomkinson, Org. Lett., 2008, 10, 797-800.

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Key Words

Hydroxylamines

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ID: J54-Y2009-0130