Supported Catalyst for Hydrogen/Deuterium Exchange

  • Author:
  • Published: 14 July 2016
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Advanced Synthesis & Catalysis/Wiley-VCH
thumbnail image: Supported Catalyst for Hydrogen/Deuterium Exchange

Replacing hydrogen atoms with the heavier isotope deuterium allows mechanistic investigations, is useful for mass spectrometry, and is important for metabolic and pharmacokinetics studies. Possible catalysts for this process are iridium(III) phosphine complexes, which can activate C–H bonds. However, they can decompose by ligand oxidation or dissociation, which limits their activity. N-heterocyclic carbene (NHC) ligands are more stable and show higher activity.

Christophe Boisson, Chloé Thieuleux, and colleagues, Université de Lyon, France, have developed a polyethylene-supported iridium(III)-NHC hydrogen/deuterium exchange catalyst with high activity, which can easily be recovered and reused due to its heterogeneous nature. The team prepared iodo-polyethylene (functionalized at the chain end) using catalyzed chain grow polymerization (CCG). The NHC was introduced by nucleophilic substitution of the iodide and addition of silver oxide to form Ag-NHC complexes. In a final step, a transmetallation was performed using [IrCp*Cl2]2 (Cp* = C5Me5) to give the finished PE-(NHC)IrCp*Cl2 catalyst (pictured).

The researchers tested the catalyst in a hydrogen/deuterium exchange reaction using different ketones as substrates. They found that it has the same high catalytic activity as a comparable homogeneous catalyst while being easy to reuse.


Article Views: 2216

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. more

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