Sonogashira coupling is one of the cornerstone Palladium mediated cross coupling reactions, giving a direct and high yield access to symmetric and non-symmetric alkynes with high tolerance of substituents. The method generally requires the use of CuI as a cocatalyst, an inert atmosphere to protect palladium catalyst, somewhat harsh conditions like prolonged heating and the use of organic solvents due to the hydrophobicity of reagents and products. Leveraging on the opportunities offered by micellar catalysis, we here present a general methodology to perform Sonogashira coupling in water, with moderate or no heating, under air, without copper co-catalysts and at very low catalyst loading. The method offers the same generality and scope of organic solvents based couplings, but strongly improves sustainability while offering excellent yields.

Ghiglietti, E., Incarbone, E., Mattiello, S., Beverina, L. (2024). Efficient Copper-Free Sonogashira Coupling in Water and under Ambient Atmosphere. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY [10.1002/ejoc.202400223].

Efficient Copper-Free Sonogashira Coupling in Water and under Ambient Atmosphere

Ghiglietti, E;Incarbone, EA;Mattiello, S
;
Beverina, L.
2024

Abstract

Sonogashira coupling is one of the cornerstone Palladium mediated cross coupling reactions, giving a direct and high yield access to symmetric and non-symmetric alkynes with high tolerance of substituents. The method generally requires the use of CuI as a cocatalyst, an inert atmosphere to protect palladium catalyst, somewhat harsh conditions like prolonged heating and the use of organic solvents due to the hydrophobicity of reagents and products. Leveraging on the opportunities offered by micellar catalysis, we here present a general methodology to perform Sonogashira coupling in water, with moderate or no heating, under air, without copper co-catalysts and at very low catalyst loading. The method offers the same generality and scope of organic solvents based couplings, but strongly improves sustainability while offering excellent yields.
Articolo in rivista - Articolo scientifico
copper-free; micellar reactions; Sonogashira coupling; surfactant;
English
5-apr-2024
2024
e202400223
reserved
Ghiglietti, E., Incarbone, E., Mattiello, S., Beverina, L. (2024). Efficient Copper-Free Sonogashira Coupling in Water and under Ambient Atmosphere. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY [10.1002/ejoc.202400223].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/475202
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