ArticleNature chemistry2017
CO- and HCl-free synthesis of acid chlorides from unsaturated hydrocarbons via shuttle catalysis.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 106 citations in OpenAlex.
- Direct Regioselective para-Fluorination via I(I)/I(III) Catalysis.Angewandte Chemie (International ed. in English) · 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
- A metal-catalysed functional group metathesis approach to the carbon isotope labelling of carboxylic acids.Nature chemistry · 2024Article
- Mechanistic Investigation of the Rhodium-Catalyzed Transfer Hydroarylation Reaction Involving Reversible C-C Bond Activation.Journal of the American Chemical Society · 2023Article
- Late-Stage Molecular Editing Enabled by Ketone Chain-Walking Isomerization.Journal of the American Chemical Society · 2023Article
- Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides.Nature communications · 2023Article
- Controlling Selectivity in Shuttle Hetero-difunctionalization Reactions: Electrochemical Transfer Halo-thiolation of Alkynes.Angewandte Chemie (International ed. in English) · 2023Article
- Enantioselective Hydrocarbamoylation of Alkenes.Angewandte Chemie (International ed. in English) · 2022Article
- NHC-BIAN-Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water.The Journal of organic chemistry · 2022Article
- Transaminase-Mediated Amine BorrowingOrganic letters · 2022Article
- Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones.Journal of the American Chemical Society · 2021Article
- Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C-COCl Bond Cleavage*.Angewandte Chemie (International ed. in English) · 2021Article
- Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange.Angewandte Chemie (International ed. in English) · 2021Article
- Fragmentation and reassembly.Nature chemistry · 2021Article
- Palladium-catalysed carboformylation of alkynes using acid chlorides as a dual carbon monoxide and carbon source.Nature chemistry · 2021Article
- Palladium catalyzed synthesis of indolizinesChemical science · 2020Article
- Palladium catalyzed carbonylative generation of potent, pyridine-based acylating electrophiles for the functionalization of arenes to ketones.Chemical science · 2020Article
- Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The synthesis of carboxylic acid derivatives from unsaturated hydrocarbons is an important process for the preparation of polymers, pharmaceuticals, cosmetics and agrochemicals. Despite its industrial relevance, the traditional Reppe-type carbonylation reaction using pressurized CO is of limited applicability to laboratory-scale synthesis because of: (1) the safety hazards associated with the use of CO, (2) the need for special equipment to handle pressurized gas, (3) the low reactivity of several relevant nucleophiles and (4) the necessity to employ different, often tailor-made, catalytic systems for each nucleophile. Herein we demonstrate that a shuttle-catalysis approach enables a CO- and HCl-free transfer process between an inexpensive reagent, butyryl chloride, and a wide range of unsaturated substrates to access the corresponding acid chlorides in good yields. This new transformation provides access to a broad range of carbonyl-containing products through the in situ transformation of the reactive acid chloride intermediate. In a broader context, this work demonstrates that isodesmic shuttle-catalysis reactions can unlock elusive catalytic reactions.
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