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Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes

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Abstract

An electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes for the synthesis of C3-functionalized 2-aryl-2,3-dihydrobenzofuran derivatives was achieved. The ring construction starts by a unique α-addition of carbon radicals derived from anodic oxidation of phenols to electron-deficient alkenes. The subsequent anodic oxidation of the resulting alkyl radical intermediates followed by trapping with the phenolic hydroxy group assembles the 2,3-dihydrobenzofuran core. Such a pathway enables the installation of various electrophilic functionalities including alkoxycarbonyl, alkylaminocarbonyl, trifluoromethyl, and cyano groups at the C-3 of the 2,3-dihydrobenzofuran framework, which is unattainable by other intermolecular reactions. The application of this method for a rapid synthesis of a bioactive natural product is demonstrated.

Graphical abstract: Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes

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Article information


Submitted
22 Feb 2020
Accepted
21 Mar 2020
First published
23 Mar 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes

Q. Zhao, J. Jin, J. Wang, F. Zhang and Y. Wang, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC01078B

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