Herein we report the design and application of a tube-in-tube packed-bed flow reactor for the first time for the development of a heterogeneous palladium catalysed oxidative C-C bond formation process. In particular, we have defined an innovative tube-in-tube protocol for the Fujiwara-Moritani C-H alkenylation reaction in biomass-derived γ-valerolactone. Thanks to this novel flow system, the oxidative C-H activation process has been conducted using a sub-stoichiometric amount of an external organic oxidant (benzoquinone) in the presence of molecular oxygen as a benign sacrificial oxidant. The protocol features very limited metal leaching and high stability of the catalyst over time. In this study, the applicability of the protocol to a range of substituted acetanilides and N-methoxybenzamides and various electron-poor alkenes has been demonstrated. The practical utility of the tube-in-tube reactor has also been proved by performing the flow methodology on a multi-gram scale.

Aerobic waste-minimized Pd-catalysed C-H alkenylation in GVL using a tube-in-tube heterogeneous flow reactor

Ferlin F.;Anastasiou I.;Carpisassi L.;Vaccaro L.
2021

Abstract

Herein we report the design and application of a tube-in-tube packed-bed flow reactor for the first time for the development of a heterogeneous palladium catalysed oxidative C-C bond formation process. In particular, we have defined an innovative tube-in-tube protocol for the Fujiwara-Moritani C-H alkenylation reaction in biomass-derived γ-valerolactone. Thanks to this novel flow system, the oxidative C-H activation process has been conducted using a sub-stoichiometric amount of an external organic oxidant (benzoquinone) in the presence of molecular oxygen as a benign sacrificial oxidant. The protocol features very limited metal leaching and high stability of the catalyst over time. In this study, the applicability of the protocol to a range of substituted acetanilides and N-methoxybenzamides and various electron-poor alkenes has been demonstrated. The practical utility of the tube-in-tube reactor has also been proved by performing the flow methodology on a multi-gram scale.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/1505883
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