Copper-catalysed low-temperature water-gas shift reaction for selective deuteration of aryl halides

Wu Li, Ruiyang Qu, Weiping Liu, Florian Bourriquen, Stephan Bartling, Nils Rockstroh, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The introduction of deuterium atoms into organic compounds is of importance for basic chemistry, material sciences, and the development of drugs in the pharmaceutical industry, specifically for identification and quantification of metabolites. Hence, methodologies for the synthesis of selectively labelled compounds continue to be a major area of interest for many scientists. Herein, we present a practical and stable heterogeneous copper catalyst, which permits for dehalogenative deuterationviawater-gas shift reaction at comparably low temperature. This novel approach allows deuteration of diverse (hetero)aryl halides with good functional group tolerance, and no reduction of the aromatic rings or other easily reducible formyl and cyano groups. Multi-gram experiments show the potential of this method in organic synthesis and medicinal chemistry.

Original languageEnglish
Pages (from-to)14033-14038
Number of pages6
JournalChemical Science
Volume12
Issue number42
DOIs
StatePublished - 14 Nov 2021
Externally publishedYes

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