Split personality of lithium chloride: recent salt effects in organometallic recipes

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64 Citations (Scopus)

Abstract

Jekyll and Hyde: Pinches of LiCl can catalyze orthometalations of halogen-substituted arenes and addition reactions of unsaturated esters, mediated by lithium diisopropylamide. Larger salt portions can transform weak organometallic bases (e.g., Grignard reagents, zincates) into “turbo” reagents of high reactivity and functional group tolerance. But the presence of LiCl, especially as an overlooked metathesis by-product can be detrimental to other catalytic reactions.
Original languageEnglish
Pages (from-to)6448-6450
Number of pages3
JournalAngewandte Chemie
Volume50
Issue number29
Early online date22 Jun 2011
DOIs
Publication statusPublished - 11 Jul 2011

Keywords

  • amides
  • lithium chloride
  • metalation
  • organolithium
  • salt effect
  • grignard-reagents
  • diisopropylamide
  • bases
  • catalysis
  • autocatalysis
  • heteroarenes
  • zincation
  • arenes
  • zinc
  • aryl

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