Manganese‐Catalysed Deuterium Labelling of Anilines and Electron‐Rich (Hetero)Arenes

There is a constant need for deuterium‐labelled products for multiple applications in life sciences and beyond. Here, a new class of heterogeneous catalysts is reported for practical deuterium incorporation in anilines, phenols, and heterocyclic substrates. The optimal material can be conveniently s...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-07, Vol.61 (27), p.e202202423-n/a
Main Authors: Bourriquen, Florian, Rockstroh, Nils, Bartling, Stephan, Junge, Kathrin, Beller, Matthias
Format: Article
Language:English
Subjects:
Aniline
Aromatic compounds
Catalysts
Deuterium
Heavy water
Heterogeneous Catalysis
Hydrogen Isotope Exchange
Labeling
Manganese
Natural products
Phenols
Starch
Substrates
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Summary:There is a constant need for deuterium‐labelled products for multiple applications in life sciences and beyond. Here, a new class of heterogeneous catalysts is reported for practical deuterium incorporation in anilines, phenols, and heterocyclic substrates. The optimal material can be conveniently synthesised and allows for high deuterium incorporation using deuterium oxide as isotope source. This new catalyst has been fully characterised and successfully applied to the labelling of natural products as well as marketed drugs. A manganese biopolymer‐supported catalyst is reported for hydrogen/deuterium exchange in anilines, phenols, heterocycles, and electron‐rich arenes. Notably, taking advantage of deuterium oxide as easy‐to‐handle isotope source, deuterated compounds are obtained in high yields in a practical manner.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202202423