Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl Halides
Top Cited Papers
- 12 July 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (31), 10028-10029
- https://doi.org/10.1021/ja064005t
Abstract
A mild, palladium-catalyzed coupling of aryl halides with ammonia or lithium amide to form primary arylamines as the major product is described. These reactions occurred with excellent selectivity for formation of the primary arylamine over formation of the diarylamine (9.5:1 to over 50:1 ratios of arylamine to diarylamine). In addition, the first organopalladium complex with a terminal −NH2 ligand has been isolated. This complex reductively eliminates to form arylamines.Keywords
This publication has 33 references indexed in Scilit:
- pH-Dependent Chemoselective Synthesis of α-Amino Acids. Reductive Amination of α-Keto Acids with Ammonia Catalyzed by Acid-Stable Iridium Hydride Complexes in WaterJournal of the American Chemical Society, 2004
- N‐Trialkylsilylimines as Coupling Partners for Pd‐Catalyzed C-N Bond‐Forming Reactions: One‐Step Synthesis of Imines and Azadienes from Aryl and Alkenyl BromidesAngewandte Chemie International Edition, 2003
- Expanding Pd-Catalyzed C−N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed ReactionsJournal of the American Chemical Society, 2003
- Palladium-Catalyzed C−N(sp2) Bond Formation: N-Arylation of Aromatic and Unsaturated Nitrogen and the Reductive Elimination Chemistry of Palladium Azolyl and Methyleneamido ComplexesJournal of the American Chemical Society, 1998
- Formation of Palladium Bis(amine) Complexes from Reaction of Amine with Palladium Tris(o-tolyl)phosphine Mono(amine) ComplexesOrganometallics, 1996
- Two‐Phase Catalysis: A Strategy for Avoiding Consecutive Reactions as Exemplified in the Telomerization of Butadiene and AmmoniaAngewandte Chemie International Edition in English, 1996
- Halide and Amine Influence in the Equilibrium Formation of Palladium Tris(o-tolyl)phosphine Mono(amine) Complexes from Palladium Aryl Halide DimersOrganometallics, 1996
- Transition metal and enzyme catalyzed reactions involving reactions with ammonia and aminesChemical Reviews, 1992
- Synthesis and reaction chemistry of monomeric and dimeric amide complexes of platinum(II)Organometallics, 1991
- Nitrogen-hydrogen activation. 1. Oxidative addition of ammonia to iridium(I). Isolation, structural characterization and reactivity of amidoiridium hydridesInorganic Chemistry, 1987