The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers

Wenhan Zhang, Joseph M. Ready

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.

Original languageEnglish (US)
Pages (from-to)8980-8984
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number34
DOIs
StatePublished - Aug 18 2014

Fingerprint

Quinolines
Naphthols
Nucleophiles
Ethers
Iodides
Hydrides
Extrusion
ketene
isobutylene

Keywords

  • arenes
  • cross-coupling
  • ketenes
  • palladium
  • synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

The ketene-surrogate coupling : Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers. / Zhang, Wenhan; Ready, Joseph M.

In: Angewandte Chemie - International Edition, Vol. 53, No. 34, 18.08.2014, p. 8980-8984.

Research output: Contribution to journalArticle

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