C-N bond activation and ring opening of a saturated N heterocyclic carbene via lateral alkali-metal-mediated metallation (AMMM)

Alberto Hernán-Gómez, Alan Kennedy, Eva Hevia

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Abstract

Combining alkali-metal mediated metalation (AMMM) and N-heterocyclic carbene (NHC) chemistry, a novel C-N bond activation and ring-opening process is described for these increasingly important NHC molecules, which are generally considered robust ancillary ligands. Here, mechanistic investigations on reactions of saturated NHC SIMes (SIMes = [:C{N(2,4,6-Me3C6H2)CH2}2]) with group 1 alkyl bases suggest this destructive process is triggered by lateral metallation of the carbene. Exploiting co-complexation and trans-metal-trapping strategies with lower polarity organometallic reagents (Mg(CH2SiMe3)2 and Al(TMP)iBu2), key intermediates in this process have been isolated and structurally defined.
Original languageEnglish
Number of pages4
JournalAngewandte Chemie International Edition
Publication statusAccepted/In press - 19 Apr 2017

Keywords

  • alkali-metal
  • C-N activation
  • metalation
  • mixed-metal chemistry
  • N-heterocyclic carbenes
  • SIMes

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