Tuning the Reactivity of a Heterogeneous Catalyst using N‐Heterocyclic Carbene Ligands for C−H Activation Reactions

• DOI: 10.1002/anie.202009258
• Publication Date: 2020-07-28T17:04:58Z
• Authors: Alberto Palazzolo; Timothée Naret; Marion Daniel‐Ber...; David‐Alexandre B...; Simon Tricard; Philippe Lesot; Yannick Coppel; Bruno Chaudret; Sophie Feuillastre; Grégory Pieters
• Keywords: Reactivity; Chemoselectivity; Homogeneous Catalysis

We report the dramatic impact of addition N-heterocyclic carbenes (NHCs) on reactivity and selectivity heterogeneous Ru catalysts in context C-H activation reactions. Using a simple robust method, we prepared series new air-stable starting from commercially available carbon (Ru/C) differently substituted NHCs. Associated with deuteration processes, depending Ru/C-NHC ratios, chemical outcome can be controlled to large extent. Indeed, tuning catalyst NHC enabled: 1) increased chemoselectivity regioselectivity for alcohols organic media; 2) synthesis fragile pharmaceutically relevant deuterated heterocycles (azine, purine) that are otherwise completely reduced using unmodified commercial catalysts; 3) discovery novel such catalysts, namely selective C-1 aldehydes.