Concepedia

Practical Imidazole‐Based Phosphine Ligands for Selective Palladium‐Catalyzed Hydroxylation of Aryl Halides

Thomas Schulz, C. Torborg, Benjamín Schäffner, Jun Huang, Alexander Zapf, Renat Kadyrov, Armin Börner, Matthias Beller

Angewandte Chemie International Edition · 2008 · 234 citations · 53 references

DOI

Concepts

Abstract

The phenol countdown: Novel imidazole-based phosphine ligands are synthesized on scales up to 100 g by a convenient lithiation–phosphorylation method. The phosphines are stable towards air and moisture and are successfully applied as ligands in the palladium-catalyzed selective hydroxylation of aryl halides (see scheme, dba=dibenzylideneacetone).

References

53

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

Expanding Pd-Catalyzed C−N Bond-Forming Processes:  The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions

Xiaohua Huang, Kevin W. Anderson, Danilo Zim et al. · Journal of the American Chemical Society · 2003 · 767 citations

, , +16

Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C−N Bond Formation with a Commercial Ligand

John F. Hartwig, Motoi Kawatsura, Sheila I. Hauck et al. · The Journal of Organic Chemistry · 1999 · 764 citations

, , +9

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 Convenient and General Method for Pd-Catalyzed Suzuki Cross-Couplings of Aryl Chlorides and Arylboronic Acids

Adam F. Littke, Gregory C. Fu · Angewandte Chemie International Edition · 1998 · 702 citations

, , +10