Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene

D.R. Armstrong, L. Balloch, William Clegg, S.H. Dale, P. Garcia-Alvarez, E. Hevia, L.M. Hogg, A.R. Kennedy, R.E. Mulvey, Charles O'Hara

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15 Citations (Scopus)

Abstract

Double role for sodium: Within a synergic sodium TMP-zincate reagent, sodium mediates the direct ortho-zincation of chlorobenzene and delivers the TMEDA ligand to nucleophilically attack the benzene ring, thereby generating novel open and cyclic zinc zwitterions (example shown). TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N,N-tetramethylethylenediamine.
Original languageEnglish
Pages (from-to)8675-8678
Number of pages4
JournalAngewandte Chemie
Volume48
Issue number46
DOIs
Publication statusPublished - 2 Nov 2009

Keywords

  • alkali metals
  • cooperative effects
  • metallacyclic compounds
  • metalation
  • zinc

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