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Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping

Uzelac, Marina and Kennedy, Alan R. and Hevia, Eva and Mulvey, Robert E. (2016) Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping. Angewandte Chemie International Edition, 55. pp. 13147-13150. ISSN 1433-7851

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This study establishes a new trans-metal-trapping (TMT) protocol based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH2SiMe3)3, GaR3] (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 which have been isolated and structurally defined.