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
Keywords
palladium - copper - alkynes - cross-coupling
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.
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.
