Tuning the Reactivity of a Heterogeneous Catalyst using N‐Heterocyclic Carbene Ligands for C−H Activation Reactions
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 av...
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| Veröffentlicht in: | Angewandte Chemie International Edition Jg. 59; H. 47; S. 20879 - 20884 |
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16.11.2020
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| Abstract | 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.
The addition of N‐heterocyclic carbenes on Ru/C induces a catalytic activity switch to favor hydrogen isotope exchange over reductive deuteration. This catalyst modification led to an increase in regio‐ and chemoselectivity in the context of the C−H deuteration of pharmaceutically relevant substructures, as well as to the discovery of a novel reactivity for such heterogeneous Ru catalysts, namely selective C‐1 deuteration of aldehydes. |
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| AbstractList | 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. Heterogeneous CatalysisTuning the Reactivity of a Heterogeneous Catalyst usingN-Heterocyclic Carbene Ligands for CH Activation ReactionsAlberto Palazzolo, TimothØe Naret, Marion Daniel-Bertrand, David-Alexandre Buisson,Simon Tricard, Philippe Lesot, Yannick Coppel, Bruno Chaudret, Sophie Feuillastre, andGrØgory Pieters*Abstract:We report the dramatic impact of the addition of N-heterocyclic carbenes (NHCs) on the reactivity and selectivityof heterogeneous Ru catalysts in the context of CH activationreactions. Using a simple and robust method, we prepareda series of new air-stable catalysts starting from commerciallyavailable Ru on carbon (Ru/C) and differently substitutedNHCs. Associated with CH deuteration processes, dependingon Ru/C-NHC ratios, the chemical outcome can be controlledto a large extent. Indeed, tuning the reactivity of the Ru catalystwith NHC enabled: 1) increased chemoselectivity and theregioselectivity for the deuteration of alcohols in organicmedia; 2) the synthesis of fragile pharmaceutically relevantdeuterated heterocycles (azine, purine) that are otherwisecompletely reduced using unmodified commercial catalysts;3) the discovery of a novel reactivity for such heterogeneous Rucatalysts, namely the selective C-1 deuteration of aldehydes 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.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. 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. 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. The addition of N‐heterocyclic carbenes on Ru/C induces a catalytic activity switch to favor hydrogen isotope exchange over reductive deuteration. This catalyst modification led to an increase in regio‐ and chemoselectivity in the context of the C−H deuteration of pharmaceutically relevant substructures, as well as to the discovery of a novel reactivity for such heterogeneous Ru catalysts, namely selective C‐1 deuteration of aldehydes. |
| Author | Lesot, Philippe Coppel, Yannick Palazzolo, Alberto Daniel‐Bertrand, Marion Feuillastre, Sophie Pieters, Grégory Tricard, Simon Chaudret, Bruno Naret, Timothée Buisson, David‐Alexandre |
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| Keywords | SELECTIVE DEUTERATION deuteration isotopic exchange HYDROGENATION heterogeneous catalysis STABILIZATION BOND FUNCTIONALIZATION RU NANOPARTICLES SULFUR ALCOHOLS C-H activation REGIOSELECTIVE DEUTERATION N-heterocyclic carbenes |
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| Snippet | 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... 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... Heterogeneous CatalysisTuning the Reactivity of a Heterogeneous Catalyst usingN-Heterocyclic Carbene Ligands for CH Activation ReactionsAlberto Palazzolo,... |
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| SubjectTerms | Alcohols Aldehydes Carbenes Catalysts Chemical Sciences Chemistry Chemistry, Multidisciplinary C−H activation Deuteration heterogeneous catalysis isotopic exchange N-heterocyclic carbenes Organic chemistry Physical Sciences Reactivity Regioselectivity Science & Technology Selectivity Tuning |
| Title | Tuning the Reactivity of a Heterogeneous Catalyst using N‐Heterocyclic Carbene Ligands for C−H Activation Reactions |
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