Carbon-Carbon Cross-Coupling Reactions under Continuous Flow Conditions Using Poly(vinylpyridine) Doped with Palladium

Abstract

Coordinative immobilization of an oxime-based palladacycle to poly(vinylpyridine)/glass composite materials shaped as Raschig rings or placed within the PASSflow^TM microreactor affords technical devices that are well suited for performing palladium-catalyzed carbon-carbon cross-coupling reactions in the flow-through mode. Reusability of the immobilized precatalyst as well as applications in the microwave field were investigated. Experiments with thiol- and pyridine-based scavengers were carried out, which revealed that the active palladium species is likely to be composed of nanoparticles of unknown nature and that the poly(vinylpyridine) carrier has scavenging properties for these particles.

Key words

palladium catalyst - immobilization - microreactor - microwave - C-C cross-coupling reactions

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29

de Vries has demonstrated that Pd nanoparticles can act as active species in solution at extremely low concentrations so that the results presented in Scheme [4] only reflects a kinetic effect.