Atom Efficient Magnesiation of N-Substituted Alkyl Indoles with a Mixed Sodium-Magnesium Base

Michael A. Stevens, Victoria L. Blair

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This study presents the alkali metal mediated magnesiation (AMMMg) of three N-alkylated indoles with the mixed Na/Mg base [(TMEDA)Na(TMP)2Mg(CH2SiMe3)] 1 (TMEDA = N,N,N′,N′-tetramethylethylenediamine, TMP = 2,2,6,6-tetramethylpiperidine). All three magnesiated indoles have been successfully characterised by single-crystal X-ray diffraction and solution state NMR studies, whereas iodolysis and Pd-catalysed cross coupling have been investigated. The steric nature of the N-alkyl group changes the reactivity and efficiency of 1 to give either atom efficient disodium tetraindol-2-ylmagnesiates [(Na-TMEDA)2Mg(α-C9H8N)4] 2 and [(Na-TMEDA)2Mg(α-C10H11N)4] 3, or [(TMEDA)Na(TMP)(α-C11H12N)Mg(TMP)] 4, whereby only one indole molecule is selectively deprotonated.

Original languageEnglish
Pages (from-to)74-79
Number of pages6
JournalEuropean Journal of Inorganic Chemistry
Issue number1
Publication statusPublished - 10 Jan 2018


  • Cross-coupling
  • Functionalised indoles
  • Iodolysis
  • Magnesiation
  • Metallation

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