Heterogeneous metallo-organocatalysis for the selective one-pot synthesis of 2-benzylidene-indoxyl and 2-phenyl-4-quinolone |
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Authors: | Marie Genelot Véronique Dufaud Laurent Djakovitch |
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Institution: | a Université de Lyon, CNRS, UMR 5256, IRCELYON, Institut de recherches sur la catalyse et l’environnement de Lyon, 2 avenue Albert Einstein, F-69626 Villeurbanne, France b Université de Lyon, CNRS, UMR 5182, Laboratoire de Chimie, Ecole Normale Supérieure de Lyon, 46 Allée d’Italie, F-69364 Lyon Cedex 07, France |
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Abstract: | One-pot tandem heterogeneously catalyzed procedures for the selective synthesis of 2-benzylidene-indoxyl and 2-phenyl-4-quinolone have been developed. For this purpose, heterogeneous palladium-, amine-, and phosphine-catalysts were prepared by post-synthetic grafting onto SBA silica. The state of the hybrid materials was characterized using a wide variety of molecular and solid-state techniques. These materials exhibit high activities as 2-benzylidene-indoxyl was obtained in 81% yields through {Pd]@SBA-15+PPh3} catalysis while 2-phenyl-4-quinolone was prepared by a fully heterogeneous {Pd]@SBA-15+AMINE]@SBA-3} protocol in 61-75% isolated yield. For the later, we demonstrated that the catalysts mixture could be reused up to three runs without strong deactivation. |
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Keywords: | Metallo-organocatalysis Heterogeneous catalysis One-pot synthesis 4-Quinolones Indoxyls Mesoporous supports |
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