Tuning the basicity of synergic bimetallic reagents: switching the regioselectivity of the direct dimetalation of toluene from 2,5-to 3,5-positions

V.L. Blair, L.M. Carrella, W. Clegg, B. Conway, R.W. Harrington, L.M. Hogg, J. Klett, R.E. Mulvey, Eva Rentschler, Luca Russo

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Abstract

Meta-meta metalation: Remarkably, toluene can be directly dimanganated or dimagnesiated at the 3,5-positions using bimetallic bases with active Me3SiCH2 ligands (see scheme, blue). In contrast, n-butyl ligands lead to 2,5-metalation (red). tmp=2,2,6,6-tetramethylpiperidide.
Original languageEnglish
Pages (from-to)6208-6211
Number of pages4
JournalAngewandte Chemie
Volume47
Issue number33
DOIs
Publication statusPublished - 4 Aug 2008

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Keywords

  • alkali metals
  • inverse crown compounds
  • magnesium
  • manganese
  • metalation

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