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

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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)13147-13150
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number42
DOIs
Publication statusPublished - 10 Oct 2016

Keywords

  • diazines
  • gallium
  • heterocyclic chemistry
  • lithiation
  • structure elucidation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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