The Ketene-Surrogate Coupling: Catalytic Conversion of Aryl Iodides into Aryl Ketenes through Ynol Ethers
作者:Wenhan Zhang、Joseph M. Ready
DOI:10.1002/anie.201405036
日期:2014.8.18
tert‐Butoxyacetylene is shown to undergo Sonogashira coupling with aryliodides 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
Synthesis of Alkyl-Ynol-Ethers by “Anti-Michael Addition” of Metal Alkoxides to β-Substituted Alkynylsulfones
作者:Leyre Marzo、Alejandro Parra、María Frías、José Alemán、José Luis García Ruano
DOI:10.1002/ejoc.201300395
日期:2013.7
alkoxides with β-substituted 2-(p-tolylsulfonyl)acetylenes, involving an anti-Michael addition reaction followed by the in situ elimination of the sulfonyl moiety, provides a direct method for the synthesis of alkyl alkynyl ethers bearing aryl or TIPS groups joined to the triple bond. Arylalkynyl ethers derived from primary alkoxides are in situ hydrolyzed into arylacetic esters.