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

Sharon E. Baillie, Victoria L. Blair, David C. Blakemore, Duncan Hay, Alan Kennedy, David C. Pryde, Eva Hevia

Research output: Contribution to journalArticle

31 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1985-1987
Number of pages3
JournalChemical Communications
Volume48
Issue number14
DOIs
Publication statusPublished - 2012

Fingerprint

Thymidine Monophosphate
Pyrazines
Alkylation
Lithium
Temperature

Keywords

  • functionalisation
  • pyrazine
  • dideprotozincation
  • nucleophilic alkylation

Cite this

Baillie, Sharon E. ; Blair, Victoria L. ; Blakemore, David C. ; Hay, Duncan ; Kennedy, Alan ; Pryde, David C. ; Hevia, Eva. / New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation. In: Chemical Communications. 2012 ; Vol. 48, No. 14. pp. 1985-1987.
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New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation. / Baillie, Sharon E.; Blair, Victoria L.; Blakemore, David C.; Hay, Duncan; Kennedy, Alan; Pryde, David C.; Hevia, Eva.

In: Chemical Communications, Vol. 48, No. 14, 2012, p. 1985-1987.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Baillie, Sharon E.

AU - Blair, Victoria L.

AU - Blakemore, David C.

AU - Hay, Duncan

AU - Kennedy, Alan

AU - Pryde, David C.

AU - Hevia, Eva

PY - 2012

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AB - 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.

KW - functionalisation

KW - pyrazine

KW - dideprotozincation

KW - nucleophilic alkylation

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U2 - 10.1039/c2cc16959b

DO - 10.1039/c2cc16959b

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