1436595-58-2Relevant academic research and scientific papers
The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers
Zhang, Wenhan,Ready, Joseph M.
supporting information, p. 8980 - 8984 (2014/11/07)
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.
Transition-metal-free synthesis of aryl-substituted tert-butyl ynol ethers through addition/elimination substitution at an sp centre
Gray, Vincent J.,Slater, Ben,Wilden, Jonathan D.
, p. 15582 - 15585 (2013/01/16)
Nucleophilic attack of an alkoxide on an alkynyl sulfonamide leads to displacement of the sulfonamide at the sp centre and isolation of the ynol ether in good yield in a single operation (see scheme). The mechanistic pathway has been probed by the use of coordinating additives, 13C-labelling experiments and ab initio calculations, which indicated that an addition/elimination mechanism is in operation. Copyright
