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 seque...

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Detalles Bibliográficos
Autores principales: Horikawa, Mami, Joy, Stephen T., Sharninghausen, Liam S., Shao, Xia, Mapp, Anna K., Scott, Peter J. H., Sanford, Melanie S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10631240/
https://www.ncbi.nlm.nih.gov/pubmed/37969612
http://dx.doi.org/10.1039/d3sc03948j
Descripción
Sumario: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.

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