Journal article

Authors list: Brand, Raoul D.; Busche, Steffen A.; Boerner, Hans G.; Smarsly, Bernd M.

Publication year: 2023

Journal: ChemCatChem

Volume number: 15

Issue number: 19

ISSN: 1867-3880

eISSN: 1867-3899

Open access status: Hybrid

DOI Link: https://doi.org/10.1002/cctc.202300778

Publisher: Wiley

Abstract: 

Organocatalysis 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.

Harvard Citation style: Brand, R., Busche, S., Boerner, H. and Smarsly, B. (2023) Peptide-based Organocatalyst on Stage: Functionalizing Mesoporous Silica by Tetrazine-Norbornene Ligation, ChemCatChem, 15(19), Article e202300778. https://doi.org/10.1002/cctc.202300778

APA Citation style: Brand, R., Busche, S., Boerner, H., & Smarsly, B. (2023). Peptide-based Organocatalyst on Stage: Functionalizing Mesoporous Silica by Tetrazine-Norbornene Ligation. ChemCatChem. 15(19), Article e202300778. https://doi.org/10.1002/cctc.202300778