ArticleAngewandte Chemie (International ed. in English)2022
S,O-Ligand Promoted meta-C-H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Functionalization of Heteroarenes via Palladium/Norbornene-Catalyzed Double C-H Activation.Accounts of chemical research · 2026Article
- A Generalized Approach for Distal C-H Arylation of Organic Building Blocks: Unveiling the Role of Counter Anion.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Fast Collective Hydrogen-Bond Dynamics in Hexafluoroisopropanol Related to its Chemical Activity.Angewandte Chemie (International ed. in English) · 2024Article
- Palladium/Norbornene-Catalyzed Direct Vicinal Di-Carbo-Functionalization of Indoles: Reaction Development and Mechanistic Study.Angewandte Chemie (International ed. in English) · 2023Article
- Mechanistic studies of the palladium-catalyzed S,O-ligand promoted C-H olefination of aromatic compounds.Chemical science · 2023Article
- S,O-Ligand Promoted meta-C-H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
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Authors and funding
4 authors.
Funding
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.
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