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- Title
Gold-Catalyzed Carbocyclization of Phenols with a Terminal Alkyne via an Intramolecular ipso-Friedel-Crafts Alkenylation.
- Authors
Nemoto, Tetsuhiro; Matsuo, Nobuaki; Hamada, Yasumasa
- Abstract
We have developed a novel synthetic method to furnish spiro[4.5]cyclohexadienones using an gold-catalyzed carbocyclization of phenols with a terminal alkyne via an intramolecular ipso-Friedel-Crafts alkenylation. Using 2-5 mol% of gold catalyst, 1 equiv. of methanesulfonic acid, and 1 equiv. of 2,6-di- tert-butylpyridine, a variety of spiro[4.5]cyclohexadienone derivatives with an exo-cyclic olefin unit was obtained in good to excellent yields. The divergent synthesis of dihydronaphthalene derivatives was also examined based on the newly developed gold catalysis.
- Subjects
GOLD catalysts; CARBOCYCLIC acids; PHENOLS; ALKENYLATION; CHEMICAL reactions; ALKENES
- Publication
Advanced Synthesis & Catalysis, 2014, Vol 356, Issue 11/12, p2417
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201400247