ArticleJournal of the American Chemical Society2020
Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Alkyne migratory functionalization via C(spNature communications · 2026Article
- Stereoselective Photoenzymatic Hydroarylation for the Construction of Quaternary Stereocenters.Journal of the American Chemical Society · 2025Article
- Facile construction of distal and diversified tertiary and quaternary stereocenters.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Remote Functionalization by Pd-Catalyzed Isomerization of Alkynyl Alcohols.Journal of the American Chemical Society · 2024Article
- Arylazo Sulfones as Nonionic Visible-Light Photoacid Generators.The Journal of organic chemistry · 2023Article
- Biocatalytic control of site-selectivity and chain length-selectivity in radical amino acid halogenases.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Parts-per-million of ruthenium catalyze the selective chain-walking reaction of terminal alkenes.Nature communications · 2022Article
- Catalytic Enantioselective Birch-Heck Sequence for the Synthesis of Phenanthridinone Derivatives with an All-Carbon Quaternary Stereocenter.The Journal of organic chemistry · 2022Article
- Palladium-catalyzed regio- and enantioselective migratory allylic C(spNature communications · 2021Article
- Stereoselective tandem iridium-catalyzed alkene isomerization-cope rearrangement of ω-diene epoxides: efficient access to acyclic 1,6-dicarbonyl compounds.Chemical science · 2021Article
- Rate Profiling the Impact of Remote Functional Groups on the Redox-Relay Heck Reaction.Organic letters · 2021Article
- Article
- Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
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Authors and funding
3 authors.
Funding
Abstract
The formation of alkyl-palladium complexes via the nucleopalladation of alkenes is the entry point for a wide range of diverse reactions. One possibility is that the intermediate alkyl-Pd complexes can undergo a "chain-walking" event, to allow for remote functionalization through various termination processes. However, there are few methods to selectively interrupt the chain-walking process at a prescribed location. Herein, we demonstrate that a variety of homoallylic protected amines undergo an interrupted enantioselective relay Heck reaction to give enantioenriched allylic amine products. The selectivity of this process can be diverted to exclusively yield the ene-amide products by virtue of changing the nature of the amine protecting group. To rationalize this observation, we combine experiment and computation to investigate the mechanism of the chain-walking process and termination events. Isotopic labeling experiments and the computed reaction pathways suggest that the system is likely under thermodynamic control, with the selectivity being driven by the relative stability of intermediates encountered during chain-walking. These results illustrate that the chain-walking of alkyl-palladium complexes can be controlled through the alteration of thermodynamic processes and provides a roadmap for exploiting these processes in future reaction development.
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