Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 47, Pages 20879-20884Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202009258
Keywords
C-H activation; deuteration; heterogeneous catalysis; isotopic exchange; N-heterocyclic carbenes
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Funding
- European Union's Horizon 2020 research and innovation program under the Marie Sklodowska-Curie grant [675071]
- ANR [ANR-17-CE11-0014]
- CEA
- CNRS
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We report the dramatic impact of the addition of N-heterocyclic carbenes (NHCs) on the reactivity and selectivity of heterogeneous Ru catalysts in the context of C-H activation reactions. Using a simple and robust method, we prepared a series of new air-stable catalysts starting from commercially available Ru on carbon (Ru/C) and differently substituted NHCs. Associated with C-H deuteration processes, depending on Ru/C-NHC ratios, the chemical outcome can be controlled to a large extent. Indeed, tuning the reactivity of the Ru catalyst with NHC enabled: 1) increased chemoselectivity and the regioselectivity for the deuteration of alcohols in organic media; 2) the synthesis of fragile pharmaceutically relevant deuterated heterocycles (azine, purine) that are otherwise completely reduced using unmodified commercial catalysts; 3) the discovery of a novel reactivity for such heterogeneous Ru catalysts, namely the selective C-1 deuteration of aldehydes.
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