Palladium-catalyzed coupling of hydroxylamines with aryl bromides, chlorides, and iodides

Achim Porzelle; Michael D Woodrow; Nicholas C O Tomkinson

doi:10.1021/ol8025022

Palladium-catalyzed coupling of hydroxylamines with aryl bromides, chlorides, and iodides

Org Lett. 2009 Jan 1;11(1):233-6. doi: 10.1021/ol8025022.

Authors

Achim Porzelle¹, Michael D Woodrow, Nicholas C O Tomkinson

Affiliation

¹ School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff CF10 3AT, UK.

PMID: 19035839
DOI: 10.1021/ol8025022

Abstract

The bis-pyrazole phosphine ligand BippyPhos is effective for the palladium-catalyzed cross-coupling of hydroxylamines with aryl bromides, chlorides, and iodides. Reactions proceed smoothly at 80 degrees C in toluene in the presence of Cs(2)CO(3) to give synthetically versatile N-arylhydroxylamine products in good to excellent yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrocarbons, Brominated / chemistry*
Hydrocarbons, Chlorinated / chemistry*
Hydrocarbons, Iodinated / chemistry*
Hydroxylamines / chemical synthesis*
Hydroxylamines / chemistry*
Ligands
Molecular Structure
Palladium / chemistry*
Stereoisomerism

Substances

Hydrocarbons, Brominated
Hydrocarbons, Chlorinated
Hydrocarbons, Iodinated
Hydroxylamines
Ligands
Palladium