Late-Stage C–H Deuteration of Arenes

  • Author: ChemistryViews
  • Published: 08 October 2021
  • Copyright: Wiley-VCH GmbH
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Late-Stage C–H Deuteration of Arenes

Organic compounds in which hydrogen atoms are replaced with the heavier isotope deuterium are useful, e.g., in investigations of reaction mechanisms, mass spectrometry studies, or drug development. Synthesizing deuterated analogues of organic compounds "from scratch" can be labor-intensive, time-consuming, and costly. Postsynthetic modifications could be an alternative. However, methods for H/D exchange, e.g., at arenes often have problems such as limited substrate scopes.

Manuel van Gemmeren, University of Münster, Germany, and colleagues have developed a palladium-catalyzed, nondirected late-stage deuteration of arenes. The team used Pd(OAc)2 as a catalyst (together with a dual-ligand system) and a mixture of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) and D2O as the solvent and a deuterium source. The researchers observed a high degree of deuterium incorporation, even for complex substrates.

The method can be used for both electron-rich and electron-poor arenes and tolerates a wide range of functional groups. The team used the approach to isotopically label a wide variety of bioactive molecules and related structures. D2O serves as a cheap and convenient deuterium source in the reactions.



Article Views: 1034

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, 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