Collect. Czech. Chem. Commun.
1999, 64, 649-672
https://doi.org/10.1135/cccc19990649
Coupling Reactions of ortho-Substituted Halobenzenes with Alkynes. The Synthesis of Phenylacetylenes and Symmetrical or Unsymmetrical 1,2-Diphenylacetylenes
Irena G. Stará*, Ivo Starý*, Adrian Kollárovič, Filip Teplý, David Šaman and Pavel Fiedler
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6, Czech Republic
Abstract
The Pd- or Pd/Cu-catalyzed coupling reactions of halobenzenes bearing the methyl, hydroxymethyl, acetoxymethyl, methoxycarbonyl, or both methoxy and 4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl groups in the ortho-position with gaseous or metallated acetylene, (trialkylsilyl)acetylenes, and arylacetylenes have been systematically studied. Various functionalized aryl- or diarylacetylenes have been synthesized in good to excellent yields. Whereas additional fluoro, nitro, or methoxy group attached to the benzene ring does not interfere in the coupling reactions, the presence of a methoxycarbonyl requires a careful optimization of reaction conditions to achieve moderate yields.
Keywords: Halobenzenes; Phenylacetylenes; Diphenylacetylenes; Cross-coupling reactions; Palladium catalysis; Arenes; Alkynes.
