Scalable and selective deuteration of (hetero)arenes

Wu Li, Jabor Rabeah, Florian Bourriquen, Dali Yang, Carsten Kreyenschulte, Nils Rockstroh, Henrik Lund, Stephan Bartling, Annette Enrica Surkus, Kathrin Junge, Angelika Brückner, Aiwen Lei, Matthias Beller

Research output: Contribution to journalArticlepeer-review

46 Scopus citations

Abstract

Isotope labelling, particularly deuteration, is an important tool for the development of new drugs, specifically for identification and quantification of metabolites. For this purpose, many efficient methodologies have been developed that allow for the small-scale synthesis of selectively deuterated compounds. Due to the development of deuterated compounds as active drug ingredients, there is a growing interest in scalable methods for deuteration. The development of methodologies for large-scale deuterium labelling in industrial settings requires technologies that are reliable, robust and scalable. Here we show that a nanostructured iron catalyst, prepared by combining cellulose with abundant iron salts, permits the selective deuteration of (hetero)arenes including anilines, phenols, indoles and other heterocycles, using inexpensive D2O under hydrogen pressure. This methodology represents an easily scalable deuteration (demonstrated by the synthesis of deuterium-containing products on the kilogram scale) and the air- and water-stable catalyst enables efficient labelling in a straightforward manner with high quality control. [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)334-341
Number of pages8
JournalNature Chemistry
Volume14
Issue number3
DOIs
StatePublished - Mar 2022
Externally publishedYes

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