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Synthesis 2008(20): 3351-3355  
DOI: 10.1055/s-0028-1083161
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© Georg Thieme Verlag Stuttgart ˙ New York

A Bio-inspired Copper Catalyst System for Practical Catalytic Cyanation of Aryl Bromides

Thomas Schareinaa, Alexander Zapfa, Alain Cottéb, Nikolaus Müllerb, Matthias Beller*a
a Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29A, 18059 Rostock, Germany
b Saltigo GmbH, Building Q 18-2, 51369 Leverkusen, Germany
Fax: +49(381)12815000; e-Mail: matthias.beller@catalysis.de;
Further Information

Publication History

Received 4 June 2008
Publication Date:
25 September 2008 (online)

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Abstract

A general and environmentally improved protocol for the cyanation of aryl halides with the nontoxic cyanide source potassium hexacyanoferrate(II) {K4[Fe(CN)6]} using copper catalysis and a ligand system based on 1-alkyl-1H-imidazoles is presented. The advantages of this system are a wide substrate range, high selectivity, easy handling, and inexpensive reagents.

Key words

copper(I) - cyanation - alkylimidazoles - bromoarenes - nitriles

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14

The price per mol CN- is 1.6 for K4[Fe(CN)6]˙3 H2O (5 kg, 99%, technical grade) and 2.0 for KCN (6 kg, 96%, technical grade); source Sigma-Aldrich Chemicals Catalogue 2008.