Premium
Mild and Efficient Copper‐Catalyzed Cyanation of Aryl Iodides and Bromides
Author(s) -
Cristau HenriJean,
Ouali Armelle,
Spindler JeanFrancis,
Taillefer Marc
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400979
Subject(s) - cyanation , chemistry , aryl , catalysis , copper , iodide , combinatorial chemistry , organic chemistry , alkyl
An efficient copper‐catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen‐ and/or oxygen‐binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper‐catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110 °C) compared with the Rosenmund–von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper‐mediated cyanation reactions.