Expedient Mechanosynthesis of N,N-Dialkyl Imidazoliums and Silver(I)-Carbene Complexes in a Ball-Mill.
The absence of solvent, associated with intensive mechanical agitation, allowed the first mechanosynthesis of high-value silver(I)-carbene complexes and the corresponding N,N-dialkylimidazolium precursors. This procedure gave outstanding results in terms of yield and reaction time, when compared to solution-based conditions previously described in literature, and was generalized to unprecedented compounds. Silver(I)-carbene complexes could either be obtained from N,N-dialkylimidazolium salts or directly from imidazole and alkyl halides in a one-pot two-step procedure without isolating the imidazolium intermediate. Additionally, an efficient one-pot three-step sequence, including imidazole alkylation, silver metalation, and transmetalation is reported.
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Place Eugène Bataillon, 34095 Montpellier cedex 5 (France).
Audrey
A
Beillard
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Place Eugène Bataillon, 34095 Montpellier cedex 5 (France).
Ethan
E
Golliard
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Place Eugène Bataillon, 34095 Montpellier cedex 5 (France).
Valentin
V
Gillet
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Place Eugène Bataillon, 34095 Montpellier cedex 5 (France). xavier.bantreil@umontpellier.fr.
Xavier
X
Bantreil
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Place Eugène Bataillon, 34095 Montpellier cedex 5 (France). txmetro@umontpellier.fr.
Thomas-Xavier
TX
Métro
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Place Eugène Bataillon, 34095 Montpellier cedex 5 (France).
Jean
J
Martinez
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Place Eugène Bataillon, 34095 Montpellier cedex 5 (France). frederic.lamaty@umontpellier.fr.
Frédéric
F
Lamaty
N-heterocylic carbenes; ball-mill; green chemistry; mechanochemical reactions; silver; solvent-free reactions