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

Mami Horikawa; Stephen T. Joy; Liam S. Sharninghausen; Xia Shao; Anna K. Mapp; Peter J. H. Scott; Melanie S. Sanford

doi:10.1039/D3SC03948J

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

Mami Horikawa,

^a Stephen T. Joy,^a Liam S. Sharninghausen,^a Xia Shao,^b Anna K. Mapp,*^a Peter J. H. Scott

*^b and Melanie S. Sanford

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, USA
E-mail: amapp@umich.edu, mssanfor@umich.edu

^b Department of Radiology, University of Michigan, 1301 Catherine, Ann Arbor, Michigan 48109, USA
E-mail: pjhscott@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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Article information

DOI: https://doi.org/10.1039/D3SC03948J
Article type: Edge Article
Submitted: 30 Jul 2023
Accepted: 20 Oct 2023
First published: 20 Oct 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2023,14, 12068-12072

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

M. Horikawa, S. T. Joy, L. S. Sharninghausen, X. Shao, A. K. Mapp, P. J. H. Scott and M. S. Sanford, Chem. Sci., 2023, 14, 12068 DOI: 10.1039/D3SC03948J

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Chemical Science

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

Abstract

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

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