ArticleJournal of the American Chemical Society2025
Ligand Design Enables the Palladium-Catalyzed Intermolecular Carbochlorocarbonylation of Alkynes and Cyclopentenone Formation.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Amide synthesis via molecular shuffling of carboxylic acids.Nature communications · 2026Article
- Intermolecular Synthesis of Coumarins from Acid Chlorides and Unactivated Alkynes through Palladium Catalysis.Organic letters · 2025Article
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Herein, we demonstrate that ligand design enables the direct addition of acid chlorides across alkynes in a single step with complete atom economy to afford α,β-unsaturated acid chloride products. This carbochlorocarbonylation reaction, which proceeds through the formal cleavage and reassembly of C-COCl bonds, was developed and explored for a range of acid chlorides and alkynes. During the course of this work, the formation of synthetically useful cyclopentenones through a formal C-H functionalization step was serendipitously observed at elevated temperatures. After optimizing for this divergent reactivity, we explored the substrate scope and undertook experiments to investigate the underlying mechanistic pathway for the formation of this product. Overall, this work expands the carbochlorocarbonylation reaction from activated substrates to alkynes. Further, it provides insight into ligand design for the exploration of fundamental reactivity.
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Registered trials
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