Expedient Mechanosynthesis of N, N‐Dialkyl Imidazoliums and Silver(I)–Carbene Complexes in a Ball‐Mill. Issue 49 (22nd October 2015)

• Record Type: Journal Article
• Authors: Beillard, Audrey; Golliard, Ethan; Gillet, Valentin; Bantreil, Xavier; Métro, Thomas‐Xavier; Martinez, Jean; Lamaty, Frédéric
• Is Part Of: Chemistry. Volume 21:Issue 49(2015)
• Page Start: 17614
• Page End: 17617
• Publication Date: 2015-10-22
• Subjects: ball‐mill -- green chemistry -- mechanochemical reactions -- N‐heterocylic carbenes -- silver -- solvent‐free reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503472
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : You only hit twice! Solvent‐free mechanochemical conditions enabled the rapid synthesis of high‐value N, N ‐dialkyl‐substituted NHC silver(I) complexes and the corresponding N, N ‐dialkylimidazolium precursors. Mechano‐metalation and transmetalation are performed in a highly user‐ and eco‐friendly approach. By using this strategy, up to three consecutive chemical steps, leading to organometallic complexes, could be performed in a ball‐mill with high efficiency.