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 inChemical communications (Cambridge, England) Vol. 48; no. 14; pp. 1985 - 1987
Main Authors Baillie, Sharon E, Blair, Victoria L, Blakemore, David C, Hay, Duncan, Kennedy, Alan R, Pryde, David C, Hevia, Eva
Format Journal Article
LanguageEnglish
Published England 14.02.2012
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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc16959b