Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 9, Pages 3702-3705Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo026592g
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Catalytic alkynylation of diverse ketones and aldehydes using nonmetallic benzyltrimethylammonium hydroxide or a basic resin of the hydroxide type in DMSO is described. Aliphatic or alicyclic carbonyl partners gave satisfactory results, whereas aromatic ones afforded products with low yields. When aromatic aldehydes were reacted with phenylacetylene, enones such as chalcone derivatives were obtained in place of ynols. These organobase-catalyzed systems provide a practical nonmetallic protocol for C-C bond formation.
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