期刊
CURRENT ORGANIC CHEMISTRY
卷 15, 期 14, 页码 2340-2361出版社
BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/138527211796150651
关键词
Cadmium; lithium; deprotonative metallation; DFT calculations; aromatic; heterocycle; cross-coupling; electrophile
Efficient deprotonative cadmiation reactions of functionalized aromatics including heterocycles have been realized using TMP-cadmiate, (TMP)(3)CdLi (TMP = 2,2,6,6-tetramethylpiperidino). The reagent is compatible with reactive functional groups (amide, ester, nitrile and even ketone functions), heavy halogens (Br, I), five-membered aromatic heterocycles (furan, thiophene, oxazole, thiazole, and pyrrole derivatives) and even aromatic aza-heterocycles (pyridine, diazine compounds). Some heterocycles benefiting from doubly activated positions can be dimetallated at room temperature. The deprotonative cadmiation pathways/mechanisms have been studied using computational/theoretical techniques. Such generated lithium arylcadmiates have been evidenced using iodine. Alternative trappings of the species are palladium-catalyzed cross-coupling reactions or simple quench with acid chlorides.
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