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Gold‐Catalyzed Cascade Cyclizations of 1,6‐Diynyl Carbonates to Benzo[<i>b</i>]fluorenes Involving Arylation of Oxocarbenium Ion Intermediates and Decarboxylative Etherification
91
Citations
55
References
2012
Year
Chemical EngineeringCascade Cyclizations6-Endo-dig CyclizationFinal Ether ProductsEngineeringAlkene MetathesisOxocarbenium Ion IntermediatesNovel OrganocatalystsCross-coupling ReactionDecarboxylative EtherificationDescribed Gold-catalyzed CycloisomerizationsOrganic ChemistryOrganometallic CatalysisCatalysisChemistryBiomolecular Engineering
Rearranged: The described gold-catalyzed cycloisomerizations give access to highly substituted benzo[b]fluorenes under mild reaction conditions (see scheme). Experimental results indicate that the in situ formed oxocarbenium ion intermediates, derived from gold-catalyzed 3,3-rearrangement and 6-endo-dig cyclization, undergo intramolecular arylation and subsequent decarboxylative etherification to furnish the final ether products.
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