C-H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling.

This report describes a net C-H radiocyanation reaction for the transformation of electron rich (hetero)aromatic substrates into 11 CN-labeled products. Electrophilic C(sp 2 )-H iodination of the (hetero)arene with N -iodosuccinimide is followed by Cu-mediated radiocyanation with K 11 CN. This sequence is applied to a variety of substrates, including the nucleobases uracil and cytosine, the amino acids tyrosine and tryptophan, and the peptide LYRAGWRAFS, which undergoes selective C-H radiocyanation at the tryptophan (W) residue.