C-H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling
Mami Horikawa1, Stephen T Joy1, Liam S Sharninghausen1
1Department of Chemistry, University of Michigan 930 North University Avenue Ann Arbor Michigan 48109 USA amapp@umich.edu mssanfor@umich.edu.
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.
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