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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| Veröffentlicht in: | Nature catalysis Jg. 3; H. 12; S. 1002 - 1009 |
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| Abstract | 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. |
|---|---|
| AbstractList | 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. 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. |
| Author | Neale, Sam Bocus, Massimo Tomkins, Patrick Van Minnebruggen, Sam Bugaev, Aram Van Speybroeck, Véronique Hajek, Julianna E. De Vos, Dirk Mali, Gregor Krajnc, Andraž Soldatov, Alexander Vercammen, Jannick |
| Author_xml | – sequence: 1 givenname: Jannick orcidid: 0000-0003-4472-330X surname: Vercammen fullname: Vercammen, Jannick organization: Centre for Membrane Separations, Adsorption, Catalysis, and Spectroscopy for Sustainable Solutions (cMACS) – sequence: 2 givenname: Massimo surname: Bocus fullname: Bocus, Massimo organization: Center for Molecular Modeling (CMM), Ghent University – sequence: 3 givenname: Sam surname: Neale fullname: Neale, Sam organization: Center for Molecular Modeling (CMM), Ghent University – sequence: 4 givenname: Aram orcidid: 0000-0001-8273-2560 surname: Bugaev fullname: Bugaev, Aram organization: The Smart Materials Research Institute, Southern Federal University – sequence: 5 givenname: Patrick surname: Tomkins fullname: Tomkins, Patrick organization: Centre for Membrane Separations, Adsorption, Catalysis, and Spectroscopy for Sustainable Solutions (cMACS) – sequence: 6 givenname: Julianna surname: Hajek fullname: Hajek, Julianna organization: Center for Molecular Modeling (CMM), Ghent University – sequence: 7 givenname: Sam surname: Van Minnebruggen fullname: Van Minnebruggen, Sam organization: Centre for Membrane Separations, Adsorption, Catalysis, and Spectroscopy for Sustainable Solutions (cMACS) – sequence: 8 givenname: Alexander orcidid: 0000-0001-8411-0546 surname: Soldatov fullname: Soldatov, Alexander organization: The Smart Materials Research Institute, Southern Federal University – sequence: 9 givenname: Andraž surname: Krajnc fullname: Krajnc, Andraž organization: Department of Inorganic Chemistry and Technology, National Institute of Chemistry – sequence: 10 givenname: Gregor orcidid: 0000-0002-9012-2495 surname: Mali fullname: Mali, Gregor organization: Department of Inorganic Chemistry and Technology, National Institute of Chemistry – sequence: 11 givenname: Véronique orcidid: 0000-0003-2206-178X surname: Van Speybroeck fullname: Van Speybroeck, Véronique email: Veronique.vanspeybroeck@ugent.be organization: Center for Molecular Modeling (CMM), Ghent University – sequence: 12 givenname: Dirk orcidid: 0000-0003-0490-9652 surname: E. De Vos fullname: E. De Vos, Dirk email: dirk.devos@kuleuven.be organization: Centre for Membrane Separations, Adsorption, Catalysis, and Spectroscopy for Sustainable Solutions (cMACS) |
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| Snippet | 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... |
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| SubjectTerms | 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 |
| Title | Shape-selective C–H activation of aromatics to biarylic compounds using molecular palladium in zeolites |
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