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

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.

SUBMITTER: Arcadi A

PROVIDER: S-EPMC8693365 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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

Arcadi Antonio A Fabrizi Giancarlo G Fochetti Andrea A Ghirga Francesca F Goggiamani Antonella A Iazzetti Antonia A Marrone Federico F Mazzoccanti Giulia G Serraiocco Andrea A

RSC advances 20201201 2

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 ...[more]

PMID: 35423668

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