S,O‐Ligand Promoted meta ‐C−H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis
Abstract: Reversing the conventional site‐selectivity of C−H activation processes provides new retrosynthetic disconnections to otherwise unreactive bonds. Here, we report a new catalytic system based on palladium/norbornene and an S,O‐ligand for the meta‐C−H arylation of aryl ethers that significantly outperforms previously reported systems. We demonstrate the unique ability of this system to employ alkoxyarene substrates bearing electron donating and withdrawing substituents. Additionally, ortho‐substituted aryl ethers are well tolerated, overcoming the “ortho constraint”, which is the necessity to have a meta‐substituent on the alkoxyarene to achieve high reaction efficiency, by enlisting novel norbornene mediators. Remarkably, for the first time the monoarylation of alkoxyarenes is achieved efficiently enabling the subsequent introduction of a second, different aryl coupling partner to rapidly furnish unsymmetrical terphenyls. Further insight into the reaction mechanism was achieved by isolation and characterization of some Pd‐complexes—before and after meta C−H activation—prior to evaluation of their respective catalytic activities.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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S,O‐Ligand Promoted meta ‐C−H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis ; day:21 ; month:06 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (21.06.2022) (gesamt 1)
- Creator
- DOI
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10.1002/anie.202201750
- URN
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urn:nbn:de:101:1-2022062115125792977446
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:31 AM CEST
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Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Sukowski, Verena
- van Borselen, Manuela
- Mathew, Simon
- Fernández‐Ibáñez, M. Ángeles
Other Objects (12)
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S,O‐Ligand Promoted meta ‐C−H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis
meta ‐C−H Arylation of Aniline Derivatives via Palladium/S,O‐Ligand/Norbornene Cooperative Catalysis
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Non‐Directed C−H Arylation of Anisole Derivatives via Pd/S,O‐Ligand Catalysis
Non‐Directed C−H Arylation of Anisole Derivatives via Pd/S,O‐Ligand Catalysis
Double Mizoroki–Heck Arylation of Terminal Alkenes in the Presence of “Ligand-Free” Palladium Catalytic Systems
Palladium-Catalyzed Enantioselective Arylation of α-Imino Esters
Palladium-Catalyzed β-Arylation of α-Amino Esters
C (sp 3)−H Arylation Promoted by a Heterogeneous Palladium‐N‐Heterocyclic Carbene Complex in Batch and Continuous Flow
Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation
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S,O‐Ligand Promoted meta ‐C−H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis
meta ‐C−H Arylation of Aniline Derivatives via Palladium/S,O‐Ligand/Norbornene Cooperative Catalysis
meta ‐C−H Arylation of Aniline Derivatives via Palladium/S,O‐Ligand/Norbornene Cooperative Catalysis
Palladium-Catalyzed Benzylic Arylation
Non‐Directed C−H Arylation of Anisole Derivatives via Pd/S,O‐Ligand Catalysis
Non‐Directed C−H Arylation of Anisole Derivatives via Pd/S,O‐Ligand Catalysis
Double Mizoroki–Heck Arylation of Terminal Alkenes in the Presence of “Ligand-Free” Palladium Catalytic Systems
Palladium-Catalyzed Enantioselective Arylation of α-Imino Esters
Palladium-Catalyzed β-Arylation of α-Amino Esters
C (sp 3)−H Arylation Promoted by a Heterogeneous Palladium‐N‐Heterocyclic Carbene Complex in Batch and Continuous Flow
Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation