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

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

Angewandte Chemie (International ed. in English) (2014-07-01)
Wenhan Zhang, Joseph M Ready
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tetrakis(triphenylphosphine)palladium(0), 99%
Sigma-Aldrich
Tetrakis(triphenylphosphine)palladium(0), ≥99.99% trace metals basis