Concepedia

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

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

Organic Letters · 2008 · 50 citations · 28 references

DOI

Concepts

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.

References

28

A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines

Anil S. Guram, Roger A. Rennels, Stephen L. Buchwald · Angewandte Chemie International Edition in English · 1995 · 1K citations

, , +7

Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents

Janis Louie, John F. Hartwig · Tetrahedron Letters · 1995 · 887 citations · Full text

, , +10

A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions:  Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl Chlorides

David W. Old, John P. Wolfe, Stephen L. Buchwald · Journal of the American Chemical Society · 1998 · 811 citations

, , +13

Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C−C, C−N, and C−O Bond-Forming Cross-Couplings

Noriyasu Kataoka, Quinetta D. Shelby, James P. Stambuli et al. · The Journal of Organic Chemistry · 2002 · 729 citations

, , +16

A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides

John P. Wolfe, Stephen L. Buchwald · Angewandte Chemie International Edition · 1999 · 706 citations · Full text

, , +14