Racys, D. T., Sharif, S. A.I., Pimlott, S. L. and Sutherland, A. (2016) Silver(I)-catalyzed iodination of Arenes: Tuning the Lewis acidity of N-iodosuccinimide activation. Journal of Organic Chemistry, 81(3), pp. 772-780. (doi: 10.1021/acs.joc.5b02761) (PMID:26795534)
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Abstract
A mild and rapid method for the iodination of arenes that utilizes silver(I) triflimide as a catalyst for activation of N-iodosuccinimide has been developed. The transformation was found to be general for a wide range of anisole, aniline, acetanilide, and phenol derivatives and allowed the late-stage iodination of biologically active compounds such as PIMBA, a SPECT imaging agent of breast cancer, and (−)-IBZM, a dopamine D2 receptor antagonist. The method was also modified for the radioiodination of arenes using a one-pot procedure involving the in situ generation of [125I]-N-iodosuccinimide followed by the silver(I)-catalyzed iodination.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Pimlott, Dr Sally and Sutherland, Professor Andrew and Racys, Dr Daugirdas |
| Authors: | Racys, D. T., Sharif, S. A.I., Pimlott, S. L., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Copyright Holders: | Copyright © 2016 The Authors |
| First Published: | First published in Journal of Organic Chemistry 81(3):772-780 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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