Issue 14, 2012
From the journal:

Chemical Communications

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

Sharon E. Baillie,a   Victoria L. Blair,a   David C. Blakemore,b   Duncan Hay,b   Alan R. Kennedy,a   David C. Prydeb  and  Eva Hevia*a  

* Corresponding authors

a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK
E-mail: eva.hevia@strath.ac.uk

b Worldwide Medicinal Chemistry, Pfizer Global Research and Development, Sandwich Laboratories, Ramsgate Road, Sandwich, Kent, UK

Abstract

Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)tBu2] (1) and [(PMDETA)LiZntBu3] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C–H alkylation of this sensitive heterocycle.

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

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Article information

DOI
https://doi.org/10.1039/C2CC16959B
Article type
Communication
Submitted
09 Nov 2011
Accepted
16 Dec 2011
First published
20 Dec 2011

Chem. Commun., 2012,48, 1985-1987

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

S. E. Baillie, V. L. Blair, D. C. Blakemore, D. Hay, A. R. Kennedy, D. C. Pryde and E. Hevia, Chem. Commun., 2012, 48, 1985 DOI: 10.1039/C2CC16959B

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