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New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation

Baillie, Sharon E. and Blair, Victoria L. and Blakemore, David C. and Hay, Duncan and Kennedy, Alan and Pryde, David C. and Hevia, Eva (2012) New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation. Chemical Communications, 48 (14). pp. 1985-1987. ISSN 1359-7345

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Abstract

Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)Bu-t(2)] (1) and [(PMDETA)(LiZnBu3)-Bu-t] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.