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Synthesis 2010(13): 2313-2318  
DOI: 10.1055/s-0029-1220008
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© Georg Thieme Verlag Stuttgart ˙ New York

Preparation of Heterocyclic Amines via a Copper(I)-Mediated Oxidative Cross-Coupling of Organozinc Reagents with Lithium Amides

Cora Dunst, Marcel Kienle, Paul Knochel*
Ludwig-Maximilians-Universität München, Department Chemie, Butenandtstrasse 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
Further Information

Publication History

Received 14 April 2010
Publication Date:
20 May 2010 (online)

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Abstract

Functionalized heteroaromatic amines are readily prepared by the oxidative coupling of polyfunctional zinc amidocuprates using PhI(OAc)2 as oxidant. Various sensitive heterocyclic organometallics undergo this oxidative cross-coupling reaction furnishing aminated heteroaromatics. A high functional group tolerance and relative insensibility to steric hindrance characterize this general amination reaction. A practical procedure for the preparation of protected primary and secondary as well as tertiary heteroaryl amines is described.

Key words

amination - amidocuprates - C-N bond formation - lithium amides - polyfunctional zinc reagents

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