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

Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)(t)Bu(2)] (1) and [(PMDETA)LiZn(t)Bu(3)] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2012-02, Vol.48 (14), p.1985-1987
Main Authors: Baillie, Sharon E, Blair, Victoria L, Blakemore, David C, Hay, Duncan, Kennedy, Alan R, Pryde, David C, Hevia, Eva
Format: Article
Language:English
Subjects:
Alkylation
Heterocyclic Compounds - chemistry
Lithium - chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Protons
Pyrazines - chemistry
Temperature
Zirconium - chemistry
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Summary:Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)(t)Bu(2)] (1) and [(PMDETA)LiZn(t)Bu(3)] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc16959b