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

doi:10.1016/j.tet.2007.02.035

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

CNRS

Research output: Contribution to journal › Article › peer-review

53 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 language	English
Pages (from-to)	3340-3349
Number of pages	10
Journal	Tetrahedron
Volume	63
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2007.02.035
State	Published - Apr 16 2007

Funding

We thank Galderma S. A. (Sophia-Antipolis) and the CNRS for financial support. We thank Yann Brouillette for his help in proof-reading the manuscript.

Funders
Galderma

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10.1016/j.tet.2007.02.035

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

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.",

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AU - Szlosek-Pinaud, Magali

AU - Diaz, Philippe

AU - Martinez, Jean

AU - Lamaty, Frédéric

N1 - Funding Information: We thank Galderma S. A. (Sophia-Antipolis) and the CNRS for financial support. We thank Yann Brouillette for his help in proof-reading the manuscript.

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AB - 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.

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DO - 10.1016/j.tet.2007.02.035

M3 - Article

AN - SCOPUS:33947109930

SN - 0040-4020

VL - 63

SP - 3340

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JO - Tetrahedron

JF - Tetrahedron

IS - 16

ER -

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

Abstract

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