Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans-Metal-Trapping

Marina Uzelac; Alan R. Kennedy; Eva Hevia; Robert E. Mulvey

doi:10.1002/anie.201607284

Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans-Metal-Trapping

Marina Uzelac, Alan R. Kennedy, Eva Hevia, Robert E. Mulvey

Department of Chemistry

University of Strathclyde

Research output: Contribution to journal › Article › peer-review

37 Citations (SciVal)

Abstract

This study establishes a new trans-metal-trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH₂SiMe₃)₃, GaR₃] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydrocarbon solution, as illustrated through reactions of pyrazine, pyridazine, and pyrimidine, as well as through the N-S heterocycle benzothiazole. The metallo-activated complexes of all of these compounds were isolated and structurally defined.

Original language	English
Pages (from-to)	13147-13150
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	42
DOIs	https://doi.org/10.1002/anie.201607284
Publication status	Published - 10 Oct 2016

Keywords

diazines
gallium
heterocyclic chemistry
lithiation
structure elucidation

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201607284Licence: CC BY

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AU - Mulvey, Robert E.

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AB - This study establishes a new trans-metal-trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH2SiMe3)3, GaR3] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydrocarbon solution, as illustrated through reactions of pyrazine, pyridazine, and pyrimidine, as well as through the N-S heterocycle benzothiazole. The metallo-activated complexes of all of these compounds were isolated and structurally defined.

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Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans-Metal-Trapping

Abstract

Keywords

ASJC Scopus subject areas

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