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

Abstract

This report describes a net C–H radiocyanation reaction for the transformation of electron rich (hetero)aromatic substrates into ¹¹CN-labeled products. Electrophilic C(sp²)–H iodination of the (hetero)arene with N-iodosuccinimide is followed by Cu-mediated radiocyanation with K¹¹CN. 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.