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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

TMP-cadmiate: A Base for Efficient and Chemoselective Deprotonative Metallation Reactions of Aromatic Compounds

Author(s): Florence Mongin and Masanobu Uchiyama

Volume 15, Issue 14, 2011

Page: [2340 - 2361] Pages: 22

DOI: 10.2174/138527211796150651

Price: $65


Efficient deprotonative cadmiation reactions of functionalized aromatics including heterocycles have been realized using TMP-cadmiate, (TMP)3CdLi (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.

Keywords: Cadmium, lithium, deprotonative metallation, DFT calculations, aromatic, heterocycle, cross-coupling, electrophile, Halopyridines, deproto-metallation, Cyanopyridines, Pyridine Esters, Bare Diazines, FERROCENES, LITHIUM ARYLCADMIATES

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