Metal-catalyzed dealkoxylative Caryl-C sp 3 cross-coupling - Replacement of aromatic methoxy groups of aryl ethers by employing a functionalized nucleophile

Matthias Leiendecker, Chien Chi Hsiao, Lin Guo, Nurtalya Alandini, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

91 Scopus citations

Abstract

The direct replacement of aromatic methoxy groups with activated carbon nucleophiles would give rise to novel synthetic pathways for targeted and diversity-oriented syntheses. We demonstrate here that this transformation can be achieved in a one-step reaction involving a bifunctional organolithium nucleophile in combination with a CAr-OMe bond-cleaving nickel catalyst. The resulting products are stable, α-CH active, and suitable for various further modifications. The direct replacement of aromatic methoxy groups with activated carbon nucleophiles would give rise to novel synthetic pathways for targeted and diversity-oriented syntheses. The use of a bifunctional nucleophile in a nickel-catalyzed cross-coupling reaction has resulted in diverse aryl methyl ethers being transformed into α-carbon-activated products.

Original languageEnglish (US)
Pages (from-to)12912-12915
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number47
DOIs
StatePublished - Nov 1 2014
Externally publishedYes

Keywords

  • aryl ethers
  • C-O bond cleavage
  • cross-coupling
  • methoxy functionalization
  • nickel

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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