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The Ketene‐Surrogate Coupling: Catalytic Conversion of Aryl Iodides into Aryl Ketenes through Ynol Ethers
Author(s) -
Zhang Wenhan,
Ready Joseph M.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405036
Subject(s) - aryl , ketene , chemistry , nucleophile , ketenimine , isobutylene , catalysis , photochemistry , medicinal chemistry , organic chemistry , polymer chemistry , alkyl , polymer , copolymer
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.