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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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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Abstract 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.
AbstractList 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.
Author Hay, Duncan
Baillie, Sharon E
Blair, Victoria L
Blakemore, David C
Hevia, Eva
Kennedy, Alan R
Pryde, David C
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Snippet 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...
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StartPage 1985
SubjectTerms Alkylation
Heterocyclic Compounds - chemistry
Lithium - chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Protons
Pyrazines - chemistry
Temperature
Zirconium - chemistry
Title New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation
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