Oxidative Intramolecular Coupling of Amidocuprates as a Novel Route to Amines and Hydrazines

Amidocuprates, derived from organocopper reagents and lithium amides upon exposure to oxygen at low temperature, provide new amine derivatives in satisfactory yields. Details of this flexible and simple methodology are given. The reaction mechanism is analyzed in terms of an oxidative intramolecular...

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Bibliographic Details
Published in:Journal of organic chemistry 1996-03, Vol.61 (5), p.1677-1681
Main Authors: Alberti, Angelo, Canè, Francesco, Dembech, Pasquale, Lazzari, Dario, Ricci, Alfredo, Seconi, Giancarlo
Format: Article
Language:English
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Summary:Amidocuprates, derived from organocopper reagents and lithium amides upon exposure to oxygen at low temperature, provide new amine derivatives in satisfactory yields. Details of this flexible and simple methodology are given. The reaction mechanism is analyzed in terms of an oxidative intramolecular coupling of aminyl radicals with the ligands on Cu in the intermediate amidocuprate. This reaction is a mild and efficient method for N-alkylation, -vinylation, and -arylation by which a number of amines, not easily accessible by normal routes, can be synthesized. Once applied to lithium hydrazides, it also provides a new and straightforward entry to N-substituted hydrazines.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9512315