Efficient synthetic approach to heterocycles possessing the 3,3-disubstituted-2,3-dihydrobenzofuran skelton via diverse palladium-catalyzed tandem reactions - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2007

Efficient synthetic approach to heterocycles possessing the 3,3-disubstituted-2,3-dihydrobenzofuran skelton via diverse palladium-catalyzed tandem reactions

Résumé

Various palladium-catalyzed cascade reactions of O-alkylated 2-iodophenol were explored in order to synthesize novel dihydrobenzofurans. An efficient tandem cyclization/anion capture reaction was developed to yield 3,3-disubstituted-2,3-dihidrobenzofurans. A small library of these compounds was prepared with a parallel organic synthesizer. A multi-component version of this reaction involving 2-iodophenol, an alkylating agent and a nucleophile, provided the same products. The methoxycarbonyl-substituted heterocyclic ring was hydrolyzed to a free acid, which could be used to further transformations.

Domaines

Chimie organique
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Dates et versions

hal-00136689 , version 1 (02-02-2021)

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Magali Sklosek-Pinaud, Philippe Diaz, Jean Martinez, Frédéric Lamaty. Efficient synthetic approach to heterocycles possessing the 3,3-disubstituted-2,3-dihydrobenzofuran skelton via diverse palladium-catalyzed tandem reactions. Tetrahedron, 2007, 63 (16), pp.3340-3349. ⟨10.1016/j.tet.2007.02.035⟩. ⟨hal-00136689⟩
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