Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp

Laia Davin, Ross McLellan, Alberto Hernán-Gómez, Bill Clegg, A R Kennedy, Iain Stepek, Maria Mertens, Eva Hevia

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Abstract

Using a specially designed magnesium metallating manifold, combining kinetically activated TMP amide base with a sterically amplified β-diketiminate ligand, this study has established a new regioselective strategy for magnesiation of challenging N-heterocyclic molecules. The broad scope of the approach is illustrated through reactions of pyrazine, triazoles and substituted pyridines through isolation and structural elucidation of their magnesiated intermediates.
Original languageEnglish
Number of pages4
JournalChemical Communications
Early online date1 Sep 2017
DOIs
Publication statusE-pub ahead of print - 1 Sep 2017

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Keywords

  • magnesium metallating manifold
  • regioselective strategy
  • magnesiation
  • N-heterocyclic molecules
  • synthesis
  • chrage density
  • deprotonative metalation

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