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

Magali Szlosek-Pinaud, Philippe Diaz, Jean Martinez, Frédéric Lamaty

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51 Scopus citations

Abstract

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-dihydrobenzofurans. 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 for further transformations.

Original languageEnglish
Pages (from-to)3340-3349
Number of pages10
JournalTetrahedron
Volume63
Issue number16
DOIs
StatePublished - Apr 16 2007

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