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Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds

✍ Scribed by Yanina Moglie; Cristian Vitale; Gabriel Radivoy

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 305 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.01.053

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✦ Synopsis

Treatment of a variety of aromatic nitro compounds with the active-iron based reducing system composed of FeCl 2 Á4H 2 O, an excess of lithium powder and a catalytic amount of 4,4 0 -di-tert-butylbiphenyl (DTBB, 5 mol %) in THF at room temperature, led to the formation of the corresponding symmetrically substituted azo compounds in good yield, resulting from a reductive coupling process. Some other functionalities including carbonyl, halogen, amino and hydroxyl groups, demonstrated to be compatible with the reaction conditions, giving none reduced or coupled by-products. In all cases, the azo compounds formed have not experienced over-reduction to the corresponding hydrazo or amino derivatives even upon prolonged heating or using an excess of the reducing system.

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