New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylationThis article is part of the ChemCom Frontiers in Molecular Main Group Chemistry web themed issue.Electronic supplementary information (ESI) available: Experimental procedures and NMR spectra. CCDC 853494853496. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c2cc16959b

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 CH alkylation of this sensitive heterocycle. Two new ligand-dep...

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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
Online Access:Get full text
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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 CH alkylation of this sensitive heterocycle. Two new ligand-dependent lithium-zincate methodologies ( via two-fold deprotonation or CH alkylation) are disclosed for the selective functionalisation of pyrazine.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc16959b