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Pd-catalyzed regiocontrolled Sonogashira and Suzuki cross-coupling reaction of 3,6-dihalogenoimidazo[1,2-a]pyridines: one-pot double-coupling approach |
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| Authors: | Ahmed El Akkaoui,Ibtissam Bassoude,Jamal Koubachi,Sabine Berteina-Raboin,Abderrahim MouaddibGé rald Guillaumet |
| Affiliation: | a Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 6005, BP 6759, 45067 Orleans Cedex 2, France b Faculté des Sciences et Téchniques, Université Sultan Moulay Slimane, BP 523, 23000 Beni-Mellal, Morocco c Laboratoire de Chimie Organique Hétérocyclique, Université Mohammed V-Agdal, Faculté des Sciences, avenue Ibn-Batouta, Rabat, Morocco |
| Abstract: | New and efficient regioselective Sonogashira and Suzuki-Miyaura palladium-catalyzed coupling reactions of 3,6-dihalogenoimidazo[1,2-a]pyridines followed by another cross-coupling has been successfully developed. Various solvents, palladium species and bases were tested. Scope and limitations of this regiocontrolled palladium-catalyzed reaction were investigated. The synthesis of 3,6-disubstituted imidazo[1,2-a]pyridine derivatives using one-pot regioselective double-coupling approach was developed. This procedure affords convergent syntheses of polysubstituted compounds in high yields in a very few steps. |
| Keywords: | Imidazo[1,2-a]pyridines One-pot Suzuki cross-coupling Sonogashira cross coupling |
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