ArticleAngewandte Chemie (International ed. in English)2021
Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters.
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 9 papers.
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9 citing papers in PubMed, 59 citations in OpenAlex.
- Regio- and Enantioselective Alkoxycarbonylation of Unactivated Terminal Alkenes under Palladium-Bromide-Monophosphine Catalysis.Journal of the American Chemical Society · 2026Article
- Switchable annulation paths to diverse N-bridged bicyclic scaffolds via ligand-directed dicarbonylation.Nature communications · 2026Article
- Synthesis of α-Substituted β,γ-Unsaturated Cyclobutanecarboxamides via Palladium-Catalyzed Aminocarbonylation of Vinylcyclobutanols.Organic letters · 2025Article
- Iron-Catalyzed Carbonylation Reactions with Carbon Monoxide.Angewandte Chemie (International ed. in English) · 2025Review
- Enantioconvergent synthesis of axially chiral amides enabled by Pd-catalyzed dynamic kinetic asymmetric aminocarbonylation.Nature communications · 2024Article
- Identification of a potent palladium-aryldiphosphine catalytic system for high-performance carbonylation of alkenes.Nature communications · 2024Article
- A Selective and General Cobalt-Catalyzed Hydroaminomethylation of Olefins to Amines.Angewandte Chemie (International ed. in English) · 2022Article
- A general strategy for the synthesis of α-trifluoromethyl- and α-perfluoroalkyl-β-lactamsChemical science · 2021Article
- Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters.Angewandte Chemie (International ed. in English) · 2021Article
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10 authors at 2 institutions in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
The dicarbonylation of 1,3-butadiene to adipic acid derivatives offers the potential for a more cost-efficient and environmentally benign industrial process. However, the complex reaction network of regioisomeric carbonylation and isomerization pathways, make a selective and direct transformation particularly difficult. Here, we report surprising solvent effects on this palladium-catalysed process in the presence of 1,2-bis-di-tert-butylphosphin-oxylene (dtbpx) ligands, which allow adipate diester formation from 1,3-butadiene, carbon monoxide, and methanol with 97 % selectivity and 100 % atom-economy under scalable conditions. Under optimal conditions a variety of di- and triesters from 1,2- and 1,3-dienes can be obtained in good to excellent yields.
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