ArticleAngewandte Chemie (International ed. in English)2021
Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C-COCl Bond Cleavage*.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 28 citations in OpenAlex.
- 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
- Ligand Design Enables the Palladium-Catalyzed Intermolecular Carbochlorocarbonylation of Alkynes and Cyclopentenone Formation.Journal of the American Chemical Society · 2025Article
- The Divergent Reactivity of Acid Chlorides Under Transition Metal Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Review
- Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C-COCl Bond Cleavage*.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 2 countries.
Funding
Abstract
Here we report a palladium-catalysed difunctionalisation of unsaturated C-C bonds with acid chlorides. Formally, the C-COCl bond of an acid chloride is cleaved and added, with complete atom economy, across either strained alkenes or a tethered alkyne to generate new acid chlorides. The transformation does not require exogenous carbon monoxide, operates under mild conditions, shows a good functional group tolerance, and gives the isolated products with excellent stereoselectivity. The intermolecular reaction tolerates both aryl- and alkenyl-substituted acid chlorides and is successful when carboxylic acids are transformed to the acid chloride in situ. The reaction also shows an example of temperature-dependent stereodivergence which, together with plausible mechanistic pathways, is investigated by DFT calculations. Moreover, we show that benzofurans can be formed in an intramolecular variant of the reaction. Finally, derivatisation of the products from the intermolecular reaction provides a highly stereoselective approach for the synthesis of tetrasubstituted cyclopentanes.
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Registered trials
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