ArticleJournal of the American Chemical Society2018
Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
26 citing papers in PubMed.
- Tropanes in natural products, syntheses, and drugs: some insights from the new millennium.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2026Review
- Understanding varenicline function via key receptor and ligand interactions.Cell reports. Physical science · 2025Article
- Regio- and Stereocontrolled-Synthesis of a Heterocycle Fragment Collection Using Palladium Catalyzed C-H Arylation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Article
- Transannular Functionalization of Multiple C(spOrganometallics · 2023Article
- PdACS catalysis · 2022Article
- Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.RSC advances · 2022Article
- Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(spChemical reviews · 2021Review
- Palladium-catalyzed C-H glycosylation and retro Diels-Alder tandem reactionChemical science · 2021Article
- Palladium-Mediated CAngewandte Chemie (International ed. in English) · 2021Article
- Emergent synthetic methods for the modular advancement of spChemical science · 2021Review
- C-H Activation: Toward Sustainability and Applications.ACS central science · 2021Review
- C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.SynOpen (2017) · 2021Article
- Diverse strategies for transition metal catalyzed distal C(spChemical science · 2020Review
- Rapid functionalization of multiple C-H bonds in unprotected alicyclic amines.Nature chemistry · 2020Article
- Functionalization of Piperidine Derivatives for the Site-Selective and Stereoselective Synthesis of Positional Analogues of Methylphenidate.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Efficient Stereoselective Carbocyclization toJournal of the American Chemical Society · 2020Article
- C─C Cleavage Approach to C─H Functionalization of Saturated Aza-Cycles.ACS catalysis · 2020Article
- Redox-Annulations of Cyclic Amines withOrganic letters · 2020Article
- Enantio- and Diastereoswitchable C-H Arylation of Methylene Groups in Cycloalkanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
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Authors and funding
3 authors.
Funding
Abstract
This article describes the development of a second-generation catalyst system for the transannular C-H functionalization of alicyclic amines. Pyridine- and quinoline-carboxylate ligands are shown to be highly effective for increasing the reaction rate, yield, and scope of Pd-catalyzed transannular C-H arylation reactions of azabicyclo[3.1.0]hexane, azabicyclo[3.1.1]heptane, azabicyclo[3.2.1]octane, and piperidine derivatives. Mechanistic studies reveal that the pyridine/quinoline-carboxylates play a role in impeding both reversible and irreversible catalyst decomposition pathways. These ligands enable the first reported examples of the transannular C-H arylation of the ubiquitous tropane, 7-azanorbornane, and homotropane cores. Finally, the pyridine/quinoline-carboxylates are shown to promote both transannular C-H arylation and transannular C-H dehydrogenation on a homotropane substrate.
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Registered trials
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