C–H Iodination of (Hetero)arenes

  • Author: ChemistryViews.org
  • Published: 15 June 2021
  • Copyright: Wiley-VCH GmbH
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: C–H Iodination of (Hetero)arenes

Aromatic compounds with iodine substituents are useful intermediates in organic synthesis. They can be prepared using electrophilic aromatic substitution reactions. However, this reaction can be hampered by a lack of regioselectivity. In addition, the substrate scope can be limited: When common iodinating reagents such as N-iodosuccinimide (NIS) are used, electron-deficient arenes and heterocycles can be difficult to convert.


Tobias Ritter, Max Planck Institute for Coal Research, Mülheim an der Ruhr, and RWTH Aachen University, both Germany, and colleagues have developed a regioselective (hetero)arene C–H iodination reaction with an improved substrate scope. The team used a combination of molecular iodine and silver mesylate. They propose that a sulfonyl hypoiodite (MeSO2–O–I) is formed from these compounds and then acts as a iodination reagent for different (hetero)arenes.


The desired iodinated products were obtained in mostly high to excellent yields. The reaction is selective and has a broad substrate scope and good functional group tolerance. With this protocol, electron-poor arenes can be iodinated—in contrast to approaches that use NIS as a reagent. The team also performed the reaction successfully on a gram scale.


 

 

Article Views: 1215

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH