Silver(I)-Catalyzed Iodination of Arenes: Tuning the Lewis Acidity of N-Iodosuccinimide Activation

The Journal of Organic Chemistry
Daugirdas T RacysAndrew Sutherland

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 [(125)I]-N-iodosuccinimide followed by the silver(I)-catalyzed iodination.

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Citations

Dec 6, 2016·Chemistry : a European Journal·Mohamed A B MostafaAndrew Sutherland
Dec 3, 2016·Angewandte Chemie·Xiaodong Xiong, Ying-Yeung Yeung
Jul 1, 2017·The Journal of Organic Chemistry·Mohamed A B MostafaAndrew Sutherland
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Nov 7, 2017·Chemistry : a European Journal·Stacey WebsterAi-Lan Lee
Aug 30, 2017·Chemical Communications : Chem Comm·Nikki L SloanAndrew Sutherland
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