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

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      Chemical Science
      The Royal Society of Chemistry

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          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 deuteration via water–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.

          Abstract

          A practical and stable heterogeneous copper catalyst has been developed for dehalogenative deuteration via water–gas shift reaction at low temperature, allowing deuteration of diverse (hetero)aryl halides with good functional group tolerance.

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          Author and article information

          Journal
          Chem Sci
          Chem Sci
          SC
          CSHCBM
          Chemical Science
          The Royal Society of Chemistry
          2041-6520
          2041-6539
          17 September 2021
          3 November 2021
          17 September 2021
          : 12
          : 42
          : 14033-14038
          Affiliations
          [a] Leibniz-Institut für Katalyse e.V. Albert-Einstein-Straße 29a 18059 Rostock Germany Kathrin.Junge@ 123456catalysis.de matthias.beller@ 123456catalysis.de
          Author information
          https://orcid.org/0000-0001-7102-4630
          https://orcid.org/0000-0003-4029-1263
          https://orcid.org/0000-0002-1064-7276
          https://orcid.org/0000-0002-3895-7321
          https://orcid.org/0000-0001-5901-7235
          https://orcid.org/0000-0001-6925-8577
          https://orcid.org/0000-0001-7044-8888
          https://orcid.org/0000-0001-5709-0965
          Article
          d1sc04259a
          10.1039/d1sc04259a
          8565366
          93b0367d-9d72-45c7-b11f-098fbc6630c4
          This journal is © The Royal Society of Chemistry
          History
          : 4 August 2021
          : 17 September 2021
          Page count
          Pages: 6
          Funding
          Funded by: H2020 European Research Council, doi 10.13039/100010663;
          Award ID: NoNaCat 670986
          Award ID: Flix 862179
          Funded by: Alexander von Humboldt-Stiftung, doi 10.13039/100005156;
          Award ID: Unassigned
          Funded by: Bundesministerium für Bildung und Forschung, doi 10.13039/501100002347;
          Award ID: Unassigned
          Categories
          Chemistry
          Custom metadata
          Paginated Article

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