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Issue 86, 2017
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Late stage iodination of biologically active agents using a one-pot process from aryl amines

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Abstract

A simple and effective one-pot tandem procedure that generates aryl iodides from readily available aryl amines via stable diazonium salts has been developed. The operationally simple procedure and mild conditions allow late-stage iodination of a wide range of aryl compounds bearing various functional groups and substitution patterns. A novel synthetic strategy involving the preparation of nitroaryl compounds followed by a chemoselective tin(II) dichloride reduction and the use of the one-pot diazotisation–iodination transformation was also developed. The general applicability of this approach was demonstrated with the preparation of a number of medicinally important compounds including CNS1261, a SPECT imaging agent of the N-methyl-D-aspartate (NMDA) receptor and IBOX, a compound used to detect amyloid plaques in the brain.

Graphical abstract: Late stage iodination of biologically active agents using a one-pot process from aryl amines

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Publication details

The article was received on 27 Oct 2017, accepted on 26 Nov 2017 and first published on 01 Dec 2017


Article type: Paper
DOI: 10.1039/C7RA11860K
Citation: RSC Adv., 2017,7, 54881-54891
  • Open access: Creative Commons BY license
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    Late stage iodination of biologically active agents using a one-pot process from aryl amines

    Nikki L. Sloan, S. K. Luthra, G. McRobbie, S. L. Pimlott and A. Sutherland, RSC Adv., 2017, 7, 54881
    DOI: 10.1039/C7RA11860K

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