Issue 21, 2021

Bsi(OTf)3-mediated tandem annulation of 1-aryl isochroman-3-ones with oxygenated arenes: one-pot synthesis of polyoxygenated homotriptycenes

Abstract

Bi(OTf)3 (bismuth triflate)-mediated one-pot tandem annulation of oxygenated 1-aryl isochroman-3-ones with oxygenated arenes provides polyoxygenated homotriptycenes in moderate to good yields in MeNO2 at reflux (101 °C) for 10 h under an air atmosphere and easy-operational conditions via intermolecular and intramolecular Friedel–Crafts type procedures. A plausible mechanism is proposed and discussed. This protocol provides a highly effective ring-closure via three carbon–carbon (C–C) bond formations.

Graphical abstract: Bsi(OTf)3-mediated tandem annulation of 1-aryl isochroman-3-ones with oxygenated arenes: one-pot synthesis of polyoxygenated homotriptycenes

Supplementary files

Article information

Article type
Paper
Submitted
30 Mar 2021
Accepted
04 May 2021
First published
05 May 2021

Org. Biomol. Chem., 2021,19, 4733-4742

Bsi(OTf)3-mediated tandem annulation of 1-aryl isochroman-3-ones with oxygenated arenes: one-pot synthesis of polyoxygenated homotriptycenes

M. Chang, C. Lin, S. Chen and Y. Hsiao, Org. Biomol. Chem., 2021, 19, 4733 DOI: 10.1039/D1OB00606A

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