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In(OTf)<sub>3</sub>-Catalyzed Synthesis of 2,3-Dihydro-1<i>H</i>-benzo[<i>e</i>]indoles and 2,3-Dihydrobenzofurans via [3 + 2] Annulation

Shuxuan Liu, Yu Zang, Hai Huang, Jianwei Sun

2020Organic Letters29 citationsDOI

Abstract

An In(OTf) 3 -catalyzed intermolecular [3 + 2] annulation for the synthesis of 2,3-dihydro-1 H -benzo[ e ]indoles and 2,3-dihydrobenzofurans from readily available substrates has been achieved. This approach takes advantage of oxetane and para -quinone methide as important functional units in the key intermediate. β-Naphthylamines and phenols have been demonstrated as excellent reaction partners.

Topics & Concepts

AnnulationChemistryOxetaneCatalysisPhenolsIntermolecular forceStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryMoleculeSynthesis of Indole DerivativesCatalytic C–H Functionalization MethodsAxial and Atropisomeric Chirality Synthesis
In(OTf)<sub>3</sub>-Catalyzed Synthesis of 2,3-Dihydro-1<i>H</i>-benzo[<i>e</i>]indoles and 2,3-Dihydrobenzofurans via [3 + 2] Annulation | Litcius