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

Research output: Contribution to journalArticle

62 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.
LanguageEnglish
Pages6448-6450
Number of pages3
JournalAngewandte Chemie
Volume50
Issue number29
Early online date22 Jun 2011
DOIs
Publication statusPublished - 11 Jul 2011

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Lithium Chloride
Personality
Salts
Halogens
Esters
diisopropylamine

Keywords

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

Cite this

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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.",
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Split personality of lithium chloride : recent salt effects in organometallic recipes. / Hevia, Eva; Mulvey, Robert E.

In: Angewandte Chemie, Vol. 50, No. 29, 11.07.2011, p. 6448-6450.

Research output: Contribution to journalArticle

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