TY - JOUR
T1 - Efficient synthetic approach to heterocycles possessing the 3,3-disubstituted-2,3-dihydrobenzofuran skeleton via diverse palladium-catalyzed tandem reactions
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.
PY - 2007/4/16
Y1 - 2007/4/16
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=33947109930&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.02.035
DO - 10.1016/j.tet.2007.02.035
M3 - Article
AN - SCOPUS:33947109930
SN - 0040-4020
VL - 63
SP - 3340
EP - 3349
JO - Tetrahedron
JF - Tetrahedron
IS - 16
ER -