JOURNAL ARTICLE

Synthesis, Characterization, and Catalytic Activity of N-Heterocyclic Carbene (NHC) Palladacycle Complexes

Mihai S. ViciuRoy A. KellyEdwin D. StevensF. NaudMartin StuderSteven P. Nolan

Year: 2003 Journal:   Organic Letters Vol: 5 (9)Pages: 1479-1482   Publisher: American Chemical Society

Abstract

Palladacycle dimers possessing bridging halides can be easily cleaved by using N-heterocyclic carbenes (NHCs) to generate novel monomeric complexes. The structure of one of these was determined by single-crystal diffraction study and consists of a square-planar coordination around the palladium center where the NHC ligand is trans to the amine of the palladacycle. The complex was found to be equally active in aryl amination and alpha-arylation of ketones even at very low catalyst loading (0.02 mol %). Primary and secondary alkyl/arylamines are equally active partners in coupling reactions. [reaction: see text]

Keywords:
Chemistry Carbene Amination Halide Aryl Palladium Catalysis Ligand (biochemistry) Alkyl Medicinal chemistry Monomer Amine gas treating Crystal structure Stereochemistry Organic chemistry

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Citation History

Topics

Catalytic Cross-Coupling Reactions
Physical Sciences →  Chemistry →  Organic Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Physical Sciences →  Chemistry →  Organic Chemistry
Catalytic C–H Functionalization Methods
Physical Sciences →  Chemistry →  Organic Chemistry
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