1. Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids
- Author
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Andrea Calcaterra, Antonia Iazzetti, Vincenzo Marsicano, Giancarlo Fabrizi, Antonella Goggiamani, Andrea Serraiocco, Andrea Fochetti, Federico Marrone, Antonio Arcadi, and Marco Chiarini
- Subjects
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 - Abstract
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.
- Published
- 2021
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