title: 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.
authors: Department of Biochemistry, Division of Chemistry, UT Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, TX 75390-0938 (USA) http://www4.utsouthwestern.edu/readylab/index.htm.
authors: Wenhan
authors: W
authors: Zhang
authors: Joseph M
authors: JM
authors: Ready
mesh_terms: D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*
chemical_list: D004987:Ethers; D005030:Ethylenes; D007454:Iodides; D007659:Ketones; C008223:ketene
keywords: arenes; cross-coupling; ketenes; palladium; synthetic methods