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Article . 2023 . Peer-reviewed
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Peptide‐based Organocatalyst on Stage: Functionalizing Mesoporous Silica by Tetrazine‐Norbornene Ligation

Authors: Raoul D. Brand; Steffen A. Busche; Hans G. Börner; Bernd M. Smarsly;

Peptide‐based Organocatalyst on Stage: Functionalizing Mesoporous Silica by Tetrazine‐Norbornene Ligation

Abstract

AbstractOrganocatalysis via the enamine mechanism developed to one of the most relevant tools in carbonyl chemistry and is widely used in asymmetric organic synthesis. In this work, a strategy is presented to conveniently immobilize a peptide‐based catalyst on silica supports for use in continuous flow catalysis reactions. A set of different porous silica supports is investigated spanning from mesoporous silica particles with defined pore sizes suitable for packed bed column reactors to silica monoliths with hierarchical meso‐macropore spaces. While the silica supports are functionalized with norbornene entities, the peptide‐based organocatalyst is modified with a tetrazine moiety, enabling the immobilization via inverse electron‐demand Diels‐Alder (IEDDA) reaction. The ligation results in catalyst loadings up to 0.2 mmol g‐1, without compromising the mesopore network. The catalytic activity of the materials is proven by the asymmetric C−C coupling reaction of n‐butanal to ß‐nitrostyrene proceeding in high yield and enantioselectivity in both batch and continuous flow setups.

Countries
Germany, Germany
Keywords

inverse electron-demand Diels-Alder reaction, 540 Chemie und zugeordnete Wissenschaften, mesoporous silica materials, ddc:540, organocatalysis, continuous flow catalysis, supported catalysis

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
10
Top 10%
Average
Top 10%
Green
hybrid