Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping

This study establishes a new trans‐metal‐trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH(2)SiMe(3))(3), GaR(3)] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydro...

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Detalles Bibliográficos
Autores principales: Uzelac, Marina, Kennedy, Alan R., Hevia, Eva, Mulvey, Robert E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113679/
https://www.ncbi.nlm.nih.gov/pubmed/27647741
http://dx.doi.org/10.1002/anie.201607284
Descripción
Sumario:This study establishes a new trans‐metal‐trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH(2)SiMe(3))(3), GaR(3)] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydrocarbon solution, as illustrated through reactions of pyrazine, pyridazine, and pyrimidine, as well as through the N‐S heterocycle benzothiazole. The metallo‐activated complexes of all of these compounds were isolated and structurally defined.

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