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

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.

SUBMITTER: Zhang W

PROVIDER: S-EPMC4134717 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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

Zhang Wenhan W Ready Joseph M JM

Angewandte Chemie (International ed. in English) 20140627 34

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. ...[more]

PMID: 24975840

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