The palladium-catalyzed synthesis of indole/benzofurancontaining 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.

Synthesis of indole/benzofuran-containing diarylmethanes through palladium-catalyzed reaction of indolylmethyl or benzofuranylmethyl acetates with boronic acids / Arcadi, A.; Calcaterra, A.; Chiarini, M.; Fabrizi, G.; Fochetti, A.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Marsicano, V.; Serraiocco, A.. - In: SYNTHESIS. - ISSN 0039-7881. - 54:3(2021), pp. 741-753. [10.1055/s-0041-1737275]

Synthesis of indole/benzofuran-containing diarylmethanes through palladium-catalyzed reaction of indolylmethyl or benzofuranylmethyl acetates with boronic acids

Calcaterra A.;Chiarini M.;Fabrizi G.;Fochetti A.;Goggiamani A.;Iazzetti A.;Marrone F.;Serraiocco A.
2021

Abstract

The palladium-catalyzed synthesis of indole/benzofurancontaining 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.
benzofurans; boronic acids; diarylmethanes; indoles; palladium; suzuki-miyaura reaction
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Synthesis of indole/benzofuran-containing diarylmethanes through palladium-catalyzed reaction of indolylmethyl or benzofuranylmethyl acetates with boronic acids / Arcadi, A.; Calcaterra, A.; Chiarini, M.; Fabrizi, G.; Fochetti, A.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Marsicano, V.; Serraiocco, A.. - In: SYNTHESIS. - ISSN 0039-7881. - 54:3(2021), pp. 741-753. [10.1055/s-0041-1737275]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1620388
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