Tuning the Reactivity of a Heterogeneous Catalyst using N-Heterocyclic Carbene Ligands for C−H Activation Reactions
Dr. Alberto Palazzolo
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDr. Timothée Naret
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDr. Marion Daniel-Bertrand
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDavid-Alexandre Buisson
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDr. Simon Tricard
LPCNO, Université de Toulouse, UMR 5215 INSA-CNRS-UPS, 135, Avenue de Rangueil, 31077 Toulouse, France
Search for more papers by this authorDr. Philippe Lesot
ICMMO, RMN en Milieu Orienté, UMR CNRS 8182, Université Paris-Saclay, Bât. 410, 91405 Orsay cedex, France
Search for more papers by this authorDr. Yannick Coppel
Laboratoire de Chimie de Coordination (LCC), CNRS, 205 route de Narbonne, BP44099, 31077 Toulouse Cedex 4, France
Search for more papers by this authorDr. Bruno Chaudret
LPCNO, Université de Toulouse, UMR 5215 INSA-CNRS-UPS, 135, Avenue de Rangueil, 31077 Toulouse, France
Search for more papers by this authorDr. Sophie Feuillastre
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorCorresponding Author
Dr. Grégory Pieters
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDr. Alberto Palazzolo
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDr. Timothée Naret
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDr. Marion Daniel-Bertrand
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDavid-Alexandre Buisson
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorDr. Simon Tricard
LPCNO, Université de Toulouse, UMR 5215 INSA-CNRS-UPS, 135, Avenue de Rangueil, 31077 Toulouse, France
Search for more papers by this authorDr. Philippe Lesot
ICMMO, RMN en Milieu Orienté, UMR CNRS 8182, Université Paris-Saclay, Bât. 410, 91405 Orsay cedex, France
Search for more papers by this authorDr. Yannick Coppel
Laboratoire de Chimie de Coordination (LCC), CNRS, 205 route de Narbonne, BP44099, 31077 Toulouse Cedex 4, France
Search for more papers by this authorDr. Bruno Chaudret
LPCNO, Université de Toulouse, UMR 5215 INSA-CNRS-UPS, 135, Avenue de Rangueil, 31077 Toulouse, France
Search for more papers by this authorDr. Sophie Feuillastre
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorCorresponding Author
Dr. Grégory Pieters
Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, 91191 Gif-sur-Yvette, France
Search for more papers by this authorAbstract
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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