Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide

W Clegg, S H Dale, E Hevia, G W Honeyman, R E Mulvey

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

The predator meets its prey in the structure of [{(iPr)2NC(Ph)(O)}Li(μ-tmp)(μ-tBu)Zn(tBu)] which reveals an aromatic amide–alkali metal zincate “precomplex” for directed ortho-metalation (DoM) that exists prior to the devouring (ortho-zincation) of the amide by the zincate. tmp=2,2,6,6-tetramethylpiperidide.
Original languageEnglish
Pages (from-to)2370-2374
Number of pages5
JournalAngewandte Chemie
Volume45
Issue number15
DOIs
Publication statusPublished - 2006

Keywords

  • alkali metals
  • amides
  • complex-induced proximity effect
  • metalation
  • zinc
  • lithiation

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