ArticleAngewandte Chemie (International ed. in English)2021
Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling.
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, 92 citations in OpenAlex.
- Access to 2,5-Disubstituted Thiazoles Via Cyclization of N-Substituted α-Amino Acids.Organic letters · 2025Article
- Metal-free highly chemo-selective bisphosphorylation and deoxyphosphorylation of carboxylic acids.Chemical science · 2023Article
- Divergent Acyl and Decarbonylative Liebeskind-Srogl Cross-Coupling of Thioesters by Cu-Cofactor and Pd-NHC (NHC = N-Heterocyclic Carbene) Catalysis.ACS catalysis · 2023Article
- Heterocyclic Suzuki-Miyaura coupling reaction of metalla-aromatics and mechanistic analysis of site selectivity.Chemical science · 2023Article
- Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls.Organic letters · 2022Article
- Decarbonylative Sonogashira Cross-Coupling: Fruitful Marriage of Alkynes with Carboxylic Acid Electrophiles.Organic chemistry frontiers : an international journal of organic chemistry · 2022Article
- Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids.Organic letters · 2021Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
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Abstract
Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper-aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.
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