Heterogeneous metallo-organocatalysis for the selective one-pot synthesis of 2-benzylidene-indoxyl and 2-phenyl-4-quinolone

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+ PPh 3 } 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. [Display omitted]