Coupling Reactions of ortho-Substituted Halobenzenes with Alkynes. The Synthesis of Phenylacetylenes and Symmetrical or Unsymmetrical 1,2-Diphenylacetylenes

[img]PDF - Authorized users only
Language: English
190Kb
Title:Coupling Reactions of ortho-Substituted Halobenzenes with Alkynes. The Synthesis of Phenylacetylenes and Symmetrical or Unsymmetrical 1,2-Diphenylacetylenes
Creators:
Stará, Irena G.
Starý, Ivo
Kollárovič, Adrian
Teplý, Filip
Šaman, David
Fiedler, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 4, pp. 649-672
Uncontrolled Keywords:Diphenylacetylenes, Halobenzenes, Palladium catalysis, Phenylacetylenes, Alkynes, Cross-coupling reactions, Arenes

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 <i>ortho</i>-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. <p>

Title:Coupling Reactions of ortho-Substituted Halobenzenes with Alkynes. The Synthesis of Phenylacetylenes and Symmetrical or Unsymmetrical 1,2-Diphenylacetylenes
Creators:
Stará, Irena G.
Starý, Ivo
Kollárovič, Adrian
Teplý, Filip
Šaman, David
Fiedler, Pavel
Uncontrolled Keywords:Diphenylacetylenes, Halobenzenes, Palladium catalysis, Phenylacetylenes, Alkynes, Cross-coupling reactions, Arenes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:4
Page Range:pp. 649-672
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990649UNSPECIFIED
ID Code:1506
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Stará, Irena G.; Starý, Ivo; Kollárovič, Adrian; Teplý, Filip; Šaman, David; Fiedler, Pavel (1999) Coupling Reactions of ortho-Substituted Halobenzenes with Alkynes. The Synthesis of Phenylacetylenes and Symmetrical or Unsymmetrical 1,2-Diphenylacetylenes. Collection of Czechoslovak Chemical Communications, 64 (4). pp. 649-672. ISSN 0010-0765

Repository Staff Only: item control page