Issue 45, 2022

A metal-free approach to highly functionalized 3-substituted-3-arylbenzofuran-2(3H)-ones

Abstract

A novel metal-free approach to the synthesis of a variety of 3-substituted-3-arylbenzofuran-2(3H)-ones is developed via H2SO4-mediated dehydrative substitution of 3-hydroxy-3-phenylbenzofuran-2(3H)-ones with electron-rich arenes/1,3-diones/alcohols/thiols as nucleophiles in moderate to good yields. Mechanistically, the substitution with the alkoxy group proceeds via a phenolic–hydroxyester intermediate, and forms the desired product via cascade dehydration–relactonization steps.

Graphical abstract: A metal-free approach to highly functionalized 3-substituted-3-arylbenzofuran-2(3H)-ones

Supplementary files

Article information

Article type
Paper
Submitted
12 Jul 2022
Accepted
18 Oct 2022
First published
25 Oct 2022

New J. Chem., 2022,46, 21906-21910

A metal-free approach to highly functionalized 3-substituted-3-arylbenzofuran-2(3H)-ones

B. B. Dhotare, S. Kumar, A. Wadawale, S. K. Nayak, M. Kumar and D. Goswami, New J. Chem., 2022, 46, 21906 DOI: 10.1039/D2NJ03404B

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