Issue 57, 2021

Copper-mediated construction of benzothieno[3,2-b]benzofurans by intramolecular dehydrogenative C–O coupling reaction

Abstract

An efficient method to synthesize benzothieno[3,2-b]benzofurans via intramolecular dehydrogenative C–H/O–H coupling has been developed. Good to excellent yields (64–91%) could be obtained no matter if the substituted group is electron-donating or electron-withdrawing. Notably, three-to-six fused ring thienofuran compounds could be constructed using this method. A reaction mechanism study showed that 1,1-diphenylethylene can completely inhibit the reaction. Therefore, it is a radical pathway initiated by single electron transfer between the hydroxyl of the substrate and the copper catalyst.

Graphical abstract: Copper-mediated construction of benzothieno[3,2-b]benzofurans by intramolecular dehydrogenative C–O coupling reaction

Supplementary files

Article information

Article type
Paper
Submitted
18 Sep 2021
Accepted
25 Oct 2021
First published
10 Nov 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 36305-36309

Copper-mediated construction of benzothieno[3,2-b]benzofurans by intramolecular dehydrogenative C–O coupling reaction

L. Ai, I. Y. Ajibola and B. Li, RSC Adv., 2021, 11, 36305 DOI: 10.1039/D1RA06985C

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