286014-42-4Relevant articles and documents
Tuning the Reactivity of a Heterogeneous Catalyst using N-Heterocyclic Carbene Ligands for C?H Activation Reactions
Buisson, David-Alexandre,Chaudret, Bruno,Coppel, Yannick,Daniel-Bertrand, Marion,Feuillastre, Sophie,Lesot, Philippe,Naret, Timothée,Palazzolo, Alberto,Pieters, Grégory,Tricard, Simon
, p. 20879 - 20884 (2020)
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.
Regioselective hydrocarbamoylation of 1-alkenes
Miyazaki, Yosuke,Yamada, Yuuya,Nakao, Yoshiaki,Hiyama, Tamejiro
supporting information; experimental part, p. 298 - 300 (2012/05/20)
Nickel/Lewis acid cooperative catalysis derived from [Ni(cod)2], AlEt3, and N-heterocyclic carbene (NHC) effects highly regioselective hydrocarbamoylation of 1-alkenes. Variously substituted formamides and 1-alkenes can be employed to give a range of linear alkanamides regioselectively.
