Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids
| Autor: | Andrea Calcaterra, Antonia Iazzetti, Vincenzo Marsicano, Giancarlo Fabrizi, Antonella Goggiamani, Andrea Serraiocco, Andrea Fochetti, Federico Marrone, Antonio Arcadi, Marco Chiarini |
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| Rok vydání: | 2021 |
| Předmět: |
Indole test
benzofurans boronic acids diarylmethanes indoles palladium suzuki-miyaura reaction Chemistry Settore CHIM/06 - CHIMICA ORGANICA Organic Chemistry chemistry.chemical_element Combinatorial chemistry palladium boronic acids Suzuki–Miyaura reaction indoles benzofurans diarylmethanes Catalysis Suzuki–Miyaura reaction chemistry.chemical_compound XPhos Benzofuran Palladium |
| Zdroj: | Synthesis. 54:741-753 |
| ISSN: | 1437-210X 0039-7881 |
| Popis: | The palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast. |
| Databáze: | OpenAIRE |
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