The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers
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.
Zhang, Wenhan,Ready, Joseph M.
supporting information
p. 8980 - 8984
(2014/11/07)
AN EFFICIENT SYNTHESIS OF tert-ALKOXYETHYNES
The synthesis of tert-butoxyethyne (1a) and (1-adamantyloxy)ethyne (1b) has been performed by a three step sequence starting from ethyl vinyl ether.Overall yields are 34 and 67percent, respectively.The process is insensitive to the steric hindrance of the tertiary alcohol used and can be conveniently modified for the preparation of 1-tert-alkoxy-1-alkynes in high yield, without isolation of the intermediate 1-tert-alkoxyethyne.
Pericas, Miquel A.,Serratosa, Felix,Valenti, Eduard
p. 2311 - 2316
(2007/10/02)
More Articles about upstream products of 89489-28-1