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Synfacts 2025; 21(01): 56
DOI: 10.1055/a-2467-6312
DOI: 10.1055/a-2467-6312
Metals in Synthesis
Copper-Accelerated Palladium-Catalyzed Cross-Coupling of Terminal Alkynes and sp2 C–X Bonds
Sonogashira K,
Tohda Y,
Hagihara N.
Osaka University, Japan
A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes, and Bromopyridines.
Tetrahedron Lett. 1975;
16: 4467-4470
DOI: 10.1016/S0040-4039(00)91094-3
A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes, and Bromopyridines.
Tetrahedron Lett. 1975;
16: 4467-4470
DOI: 10.1016/S0040-4039(00)91094-3
Significance
Three decades ago Sonogashira et al. reported the cross-coupling of terminal alkynes with sp2 C–X bonds. They reported the coupling of various vinylic bromides and (hetero)aryl iodides and bromides with acetylene, phenylacetylene, and propargyl alcohol.
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Comment
The authors build upon previous work coupling copper acetylides with iodoarenes and iodoalkenes. They were able to generate a copper acetylide in situ from a terminal alkyne, copper iodide, and diethylamine. The reaction is very efficient for the synthesis of internal alkynes.
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Publication History
Article published online:
20 December 2024
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