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DOI: 10.1055/sos-SD-019-00127

Subramanian, L. R.Science of Synthesis, (200419182.

Both 13C- and 14C-labeled aryl cyanides are of interest because they can be converted into versatile labeled synthetic intermediates such as carboxylic acids, primary amides, benzylamines, and aldehydes. To avoid having to prepare the labeled copper(I) cyanide, readily available labeled potassium cyanide is used as the cyano transfer reagent for aryl iodides to afford labeled aryl cyanides.[‌47‌] This works well in the presence of 0.5 equivalents of copper(I) iodide in refluxing 1-methylpyrrolidin-2-one, e.g. the preparation of 9-benzyl-7-fluoro-9H-carbazole-2-(1-13C)-carbonitrile (31) from the iodide 30 (Scheme 12).[‌47‌] Dimethylformamide and dimethylacetamide have also been used as solvents in certain cases. Fluorine substituents are not affected, and in one example the iodo group is selectively cyanated even when a bromo substituent is present. Otherwise, in compounds with mixed halogen substituents, each halide is replaced by cyano groups in differing proportions.

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