Shape-selective C–H activation of aromatics to biarylic compounds using molecular palladium in zeolites

The selective activation of inert C–H bonds has emerged as a promising tool for avoiding the use of wasteful traditional coupling reactions. Oxidative coupling of simple aromatics allows for a cost-effective synthesis of biaryls. However, utilization of this technology is severely hampered by poor r...

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Published in:Nature catalysis Vol. 3; no. 12; pp. 1002 - 1009
Main Authors: Vercammen, Jannick, Bocus, Massimo, Neale, Sam, Bugaev, Aram, Tomkins, Patrick, Hajek, Julianna, Van Minnebruggen, Sam, Soldatov, Alexander, Krajnc, Andraž, Mali, Gregor, Van Speybroeck, Véronique, E. De Vos, Dirk
Format: Journal Article
Language:English
Published: London Nature Publishing Group UK 01.12.2020
Nature Publishing Group
Subjects:
639/638/298
639/638/77/887
Acids
Aromatic compounds
Catalysis
Catalysts
Chemical reactions
Chemistry
Chemistry and Materials Science
Confinement
Dehydrogenation
Ligands
Nanoparticles
Organic chemicals
Palladium
Porous materials
Regioselectivity
Selectivity
Toluene
Transition metals
Zeolites
ISSN:2520-1158, 2520-1158
Online Access:Get full text
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Summary:The selective activation of inert C–H bonds has emerged as a promising tool for avoiding the use of wasteful traditional coupling reactions. Oxidative coupling of simple aromatics allows for a cost-effective synthesis of biaryls. However, utilization of this technology is severely hampered by poor regioselectivity and by the limited stability of state-of-the-art homogeneous Pd catalysts. Here, we show that confinement of cationic Pd in the pores of a zeolite allows for the shape-selective C–H activation of simple aromatics without a functional handle or electronic bias. For instance, out of six possible isomers, 4,4′-bitolyl is produced with high shape selectivity (80%) in oxidative toluene coupling on Pd-Beta. Not only is a robust, heterogeneous catalytic system obtained, but this concept is also set to control the selectivity in transition-metal-catalysed arene C–H activation through spatial confinement in zeolite pores. Controlling the regioselectivity in the coupling of simple aromatics is challenging. Now, para – para selectivity is achieved during the aerobic dehydrogenative homocoupling of arenes through a shape-selective catalyst based on molecular palladium confined within the framework of zeolite materials.
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ISSN:2520-1158
2520-1158
DOI:10.1038/s41929-020-00533-6