Palladium(II)-Catalyzed Intramolecular Aminobromination and Aminochlorination of Olefins

The first intramolecular aminobromination and aminochlorination of olefins catalyzed by palladium(II) is reported. These reactions use a stoichiometric amount of copper(II) halide salt to aid in halogen transfer and catalyst oxidation. The yields are generally high and the degree of regioselectivity...

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Bibliographic Details
Published in:Organometallics 2004-11, Vol.23 (23), p.5618-5621
Main Authors: Manzoni, Maria R, Zabawa, Thomas P, Kasi, Dhanalakshmi, Chemler, Sherry R
Format: Article
Language:English
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Summary:The first intramolecular aminobromination and aminochlorination of olefins catalyzed by palladium(II) is reported. These reactions use a stoichiometric amount of copper(II) halide salt to aid in halogen transfer and catalyst oxidation. The yields are generally high and the degree of regioselectivity (endo vs exo cyclization) varies with substrate structure. Control experiments were performed to determine the requirements for a catalytic reaction. Solvent, temperature, and the nature of the copper halide salt all effect the course of the reaction.
ISSN:0276-7333
1520-6041
DOI:10.1021/om049432z