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

Daugirdas T. Racys | Zendy; Salaheddin Sharif | Zendy; Sally L. Pimlott | Zendy; Andrew Sutherland | Zendy

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

Author(s) -

Daugirdas T. Racys,

Salaheddin Sharif,

Sally L. Pimlott,

Andrew Sutherland

Publication year - 2016

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.5b02761

Subject(s) - halogenation , acetanilide , anisole , chemistry , aniline , catalysis , combinatorial chemistry , phenol , organic chemistry , medicinal chemistry

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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