The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles has been investigated. The success of the reaction is dramatically influenced by the choice of catalytic system: with nitrogen based nucleophiles the reaction works well with Pd2(dba)3/ dppf, while with sulfur, oxygen and carbo-nucleophiles [Pd(η3-C3H5)Cl]2/XPhos is more efficient. The regiochemical outcome shows that the nucleophilic substitution occurs only on the benzylic position of the η3-(benzofuryl)methyl complex. The high to excellent yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2-substituted benzo[b]furans.

Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles / Arcadi, Antonio; Fabrizi, Giancarlo; Fochetti, Andrea; Ghirga, Francesca; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Mazzoccanti, Giulia; Serraiocco, Andrea. - In: RSC ADVANCES. - ISSN 2046-2069. - (2021), pp. 909-917. [10.1039/d0ra09601f]

Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles

Antonio Arcadi;Giancarlo Fabrizi;Andrea Fochetti;Antonella Goggiamani
;
Antonia Iazzetti
;
Federico Marrone;Giulia Mazzoccanti;Andrea Serraiocco
2021

Abstract

The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles has been investigated. The success of the reaction is dramatically influenced by the choice of catalytic system: with nitrogen based nucleophiles the reaction works well with Pd2(dba)3/ dppf, while with sulfur, oxygen and carbo-nucleophiles [Pd(η3-C3H5)Cl]2/XPhos is more efficient. The regiochemical outcome shows that the nucleophilic substitution occurs only on the benzylic position of the η3-(benzofuryl)methyl complex. The high to excellent yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2-substituted benzo[b]furans.
Benzofuran; palladium catalysis; Tsuji–Trost-type reaction; organic synthesis
01 Pubblicazione su rivista::01a Articolo in rivista
Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles / Arcadi, Antonio; Fabrizi, Giancarlo; Fochetti, Andrea; Ghirga, Francesca; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Mazzoccanti, Giulia; Serraiocco, Andrea. - In: RSC ADVANCES. - ISSN 2046-2069. - (2021), pp. 909-917. [10.1039/d0ra09601f]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1492599
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