Palladium-Catalyzed Carbonylative α-Arylation of tert-Butyl Cyanoacetate with (Hetero)aryl Bromides
| Autor: | Anders T. Lindhardt, Troels Skrydstrup, Mikkel F. Jacobsen, Dennis U. Nielsen, Mikkel T. Jensen, Martin Juhl |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Decarboxylation Aryl Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Deprotonation chemistry Functional group Organic chemistry Stoichiometry Palladium Carbon monoxide |
| Zdroj: | Jensen, M T, Juhl, M, Nielsen, D U, Jacobsen, M F, Lindhardt, A T & Skrydstrup, T 2016, ' Palladium-Catalyzed Carbonylative α-Arylation of tert-Butyl Cyanoacetate with (Hetero)aryl Bromides ', The Journal of Organic Chemistry, vol. 81, no. 4, pp. 1358-1366 . https://doi.org/10.1021/acs.joc.5b02897 |
| DOI: | 10.1021/acs.joc.5b02897 |
| Popis: | A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and dicyclohexylmethylamine for the deprotonation step, an excellent functional group tolerance was ensured for the methodology. Through the use of (13)C-labeled carbon monoxide generated from (13)COgen, the corresponding (13)C-isotopically labeled β-ketonitriles were obtained, and these products could subsequently be converted into cyanoalkynes and 3-cyanobenzofurans with site specific (13)C-isotope labeling. |
| Databáze: | OpenAIRE |
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