期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 58, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202201897
关键词
amides; calcium; calcocenes; in situ Grignard metalation method; metalation reactions
资金
- German Environment Foundation (Deutsche Bundesstiftung Umwelt, DBU) [20018/578]
- Projekt DEAL
The in situ Grignard Metalation Method (iGMM) is a straightforward strategy to synthesize alkaline-earth metal amides in high yields. It offers advantages such as no need for calcium activation and the ability to prepare large amounts of reagents. However, steric factors limit its applicability, and bulky amidines cannot be converted directly using this method.
The in situ Grignard Metalation Method (iGMM) is a straightforward one-pot strategy to synthesize alkaline-earth metal amides in multi-gram scale with high yields via addition of bromoethane to an ethereal suspension of a primary or secondary amine and magnesium (Part I) or calcium (Part II). This method is highly advantageous because no activation of calcium is required prior to the reaction. Contrary to the magnesium-based iGMM, there are some limitations, the most conspicuous one is the large influence of steric factors. The preparation of Ca(hmds)(2) succeeds smoothly within a few hours with excellent yields opening the opportunity to prepare large amounts of this reagent. Side reactions and transfer of the iGMM to substituted anilines and N-heterocycles as well as other H-acidic substrates such as cyclopentadienes are studied. Bulky amidines cannot be converted directly to calcium amidinates via the iGMM but stoichiometric calciation with Ca(hmds)(2) enables their preparation.
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