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Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light

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Abstract

The phenolate anion was discovered as a new photocatalyst with strong reduction potentials. Under visible light irradiation, the phenolate anion enabled the reduction of (hetero)aryl halides (including electron-rich aryl chlorides) to (hetero)aryl radicals through single electron transfer. Based on this new photocatalyst, a novel and efficient photocatalytic protocol for the intermolecular oxyarylation of olefins with aryl halides and TEMPOH was developed. The developed three-component coupling reaction proceeded under redox-neutral reaction conditions with stable and readily available synthons and exhibited broad substrate scope. The utility of this process was further highlighted by the diversified chemical manipulation of the resulting oxyarylation products and the late-stage modification of active pharmaceutical ingredients.

Graphical abstract: Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light

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Article information


Submitted
16 Apr 2020
Accepted
02 Jun 2020
First published
04 Jun 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

Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light

K. Liang, Q. Liu, L. Shen, X. Li, D. Wei, L. Zheng and C. Xia, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02160A

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