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Research Article Open access CC BY 4.0

A New Rapid and Specific Iodination Reagent for Phenolic Compounds

Till Hauenschild, Dariush Hinderberger

Organics · pp. 137–145 · Published 4 Apr 2023

10.3390/org4020011

Abstract

A new rapid iodination reagent, N1,N3,N5-tris[(2,4,6-trimethylpyridine)iodo(I)]-2,4,6-triphenyl-s-triazine trihexafluorophosphate, was synthesized in a modification of the established synthesis of 2,4,6-triiodo-3,5-dimethylphenol in the presence of bis(2,4,6-trimethylpyridine)iodo(I) hexafluorophosphate and used for the precise post-modification of mono- and trisubstituted phenyl compounds. We performed triple iodinations with our new phenyl-based compounds as a proof of principle of selected types of phenols, ß-sympatholytic agents and their spin-labeled derivatives, which can be employed in electron paramagnetic resonance (EPR) spectroscopy. The new rapid iodination reagent can be employed with high reactivity and regioselectivity.

Reagent Halogenation Chemistry Hexafluorophosphate Regioselectivity Electron paramagnetic resonance Reactivity (psychology) Phenols

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