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Synlett 2010(14): 2101-2105  
DOI: 10.1055/s-0030-1258523
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Selective Copper-Promoted Cross-Coupling of Aromatic Amines with Alkyl Boronic Acids

Marta Larrosa, César Guerrero, Ramón Rodríguez, Jacobo Cruces*
GalChimia, S.L., R&D Department, Cebreiro s/n, 15823 O Pino, A Coruña, Spain
Fax: +34(981)814507; e-Mail: jacobo.cruces@galchimia.com;
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Publication History

Received 23 March 2010
Publication Date:
27 July 2010 (online)

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Abstract

A simple copper-promoted N-monoalkylation of anilines that utilizes alkyl boronic acids as the alkylating partner is presented. The reaction is carried out in refluxing dioxane, and it allows a number of structurally and electronically diverse anilines to be functionalized in a single step. A broad study was carried out to demonstrate the utility of this new methodology for the preparation of phenethylanilines.

Key words

alkylation - copper - cross-coupling - boron - amines

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