Rhodium catalyzed cyanide-free cyanation of aryl halide by using formamide as a cyanide source

This work reports rhodium–xantphos as a new catalytic system for cyanide-free cyanation of aryl halides to aryl nitriles. The reaction takes place in the presence of phosphorous oxychloride as an acid and formamide as a cyanide source cum solvent. The developed protocol avoids the use of highly toxi...

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Bibliographic Details
Published in:Tetrahedron letters 2013-05, Vol.54 (21), p.2682-2684
Main Authors: Khemnar, Ashok B., Sawant, Dinesh N., Bhanage, Bhalchandra M.
Format: Article
Language:English
Subjects:
Aromatic compounds
Aryl halides
Cyanation
Cyanides
Formamide
Halides
Iodides
Rhodium
Solvents
Tetrahedrons
Toxicology
Xantphos
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Summary:This work reports rhodium–xantphos as a new catalytic system for cyanide-free cyanation of aryl halides to aryl nitriles. The reaction takes place in the presence of phosphorous oxychloride as an acid and formamide as a cyanide source cum solvent. The developed protocol avoids the use of highly toxic metal cyanides. This methodology is a simple, single step reaction involving formamide as a safe and nontoxic source of cyanation. A variety of aryl iodides/bromides were well tolerated under optimized reaction conditions providing moderate to excellent yield of corresponding cyanides.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.03.052