Elaboration of Diaryl Ketones into Naphthalenes Fused on Two or Four Sides: A Naphthoannulation Procedure
- 24 February 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (10) , 3108-3112
- https://doi.org/10.1021/ja038254i
Abstract
Transition metal-catalyzed double ring closures of 1,1-diaryl-2,2-diethynylethylenes yield polycyclic aromatic hydrocarbons and heterocycles that contain a newly formed naphthalene ring system embedded in a larger polycyclic network. The diynes required for this procedure are readily synthesized from diaryl ketones by the Corey−Fuchs olefination and subsequent Sonogashira coupling with trimethylsilylacetylene followed by desilylation. This procedure provides easy access to new compounds such as 3,11-di-tert-butyl[4]helicene and 1,8,9-perinaphthothioxanthene. Double naphthoannulation of 9,10-anthraquinone by this procedure closes four new benzene rings in a single operation to give coronene, although the yield in this case is presently low.Keywords
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