ArticleAngewandte Chemie (International ed. in English)2021
Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange.
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 7 papers.
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7 citing papers in PubMed.
- P-Directed and Lewis Acid-Assisted Pd-Catalyzed Si─Me Bond Activation Enabling Alkyl Exchange at Silicon.Angewandte Chemie (International ed. in English) · 2026Article
- 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
- Formation of C(spJournal of the American Chemical Society · 2023Article
- Rhodium-Catalyzed Anti-Markovnikov Transfer Hydroiodination of Terminal Alkynes.Angewandte Chemie (International ed. in English) · 2023Article
- Nickel-catalysed diversification of phosphine ligands by formal substitution at phosphorus.Chemical science · 2022Article
- Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange.Angewandte Chemie (International ed. in English) · 2021Article
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5 authors.
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Abstract
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C-P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
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