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:
“Christianity was only a very strong and singularly well-timed Salvation Army movement that happened to receive help from an unusual and highly dramatic incident. It was a Puritan reaction in an age when, no doubt, a Puritan reaction was much wanted; but like all sudden violent reactions, it soon wanted reacting against.”
—Samuel Butler (1835–1902)
“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)