Reaction Conditions
The Sonogashira reaction is typically run under mild conditions. The cross-coupling is carried out at room temperature with a base, typically an amine, such as diethylamine, that also acts as the solvent. The reaction medium must be basic to neutralize the hydrogen halide produced as the byproduct of this coupling reaction, so alkylamine compounds such as triethylamine and diethylamine are sometimes used as solvents, but also DMF or ether can be used as solvent. Other bases such as potassium carbonate or cesium carbonate are occasionally used. In addition, deaerated conditions are formally needed for Sonogashira coupling reactions because the palladium(0) complexes are unstable in the air, and oxygen promotes the formation of homocoupled acetylenes. Recently, development of air-stable organopalladium catalysts enable this reaction to be conducted in the ambient atmosphere.
Depending on the sp2-carbon halide-or triflate used, these reaction conditions have varying results.
Read more about this topic: Sonogashira Coupling
Famous quotes containing the words reaction and/or conditions:
“An actor must communicate his author’s given message—comedy, tragedy, serio- comedy; then comes his unique moment, as he is confronted by the looked-for, yet at times unexpected, reaction of the audience. This split second is his; he is in command of his medium; the effect vanishes into thin air; but that moment has a power all its own and, like power in any form, is stimulating and alluring.”
—Eleanor Robson Belmont (1878–1979)
“Mankind always sets itself only such tasks as it can solve; since, looking at the matter more closely, we will always find that the task itself arises only when the material conditions necessary for its solution already exist or are at least in the process of formation.”
—Karl Marx (1818–1883)