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Expedient Mechanosynthesis of N , N ‐Dialkyl Imidazoliums and Silver(I)–Carbene Complexes in a Ball‐Mill
Author(s) -
Beillard Audrey,
Golliard Ethan,
Gillet Valentin,
Bantreil Xavier,
Métro ThomasXavier,
Martinez Jean,
Lamaty Frédéric
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503472
Subject(s) - mechanosynthesis , carbene , metalation , chemistry , transmetalation , imidazole , alkyl , alkylation , halide , yield (engineering) , medicinal chemistry , organic chemistry , solvent , mechanochemistry , polymer chemistry , ball mill , materials science , catalysis , metallurgy , composite material
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.