Photocatalysis 1,6‐Addition for Site‐Selective Alkylation of <i>para</i> ‐Quinone Methides ( <i>p</i> ‐QMs) <i>via</i> Amidyl Radical 1,2‐Hydrogen Atom Transfer

Under light irradiation, a novel photocatalytic reaction between para ‐quinone methides ( p ‐QMs) and N ‐benzoyloxyamides has been developed to synthesize substituted diarylmethane derivatives, which exhibit potential biological activities. This reaction proceeds under mild conditions, affording 39 compounds with good yields and broad substrate applicability. Mechanistic studies reveal that N ‐benzoyloxyamides undergo 1,2‐hydrogen atom transfer (1,2‐HAT) to generate carbon‐centered radicals, which subsequently undergo selective radical–radical coupling with p ‐QMs to form the diarylmethane framework.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-11-10
DOI
https://doi.org/10.1002/ejoc.202500819
Primary Topic
Synthesis of Indole Derivatives
Type
article
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article

Photocatalysis 1,6‐Addition for Site‐Selective Alkylation of para ‐Quinone Methides ( p ‐QMs) via Amidyl Radical 1,2‐Hydrogen Atom Transfer

Guanghui Lv, Liulin Jiao, Yong Wu, Shiyun He et al.
European Journal of Organic Chemistry
Synthesis of Indole Derivatives
article

Photocatalysis 1,6‐Addition for Site‐Selective Alkylation of para ‐Quinone Methides ( p ‐QMs) via Amidyl Radical 1,2‐Hydrogen Atom Transfer

Guanghui Lv, Liulin Jiao, Yong Wu, Shiyun He, Li Li, Li Hai, Zhongzhen Yang, Hongying Fan
article en

Abstract

Under light irradiation, a novel photocatalytic reaction between para ‐quinone methides ( p ‐QMs) and N ‐benzoyloxyamides has been developed to synthesize substituted diarylmethane derivatives, which exhibit potential biological activities. This reaction proceeds under mild conditions, affording 39 compounds with good yields and broad substrate applicability. Mechanistic studies reveal that N ‐benzoyloxyamides undergo 1,2‐hydrogen atom transfer (1,2‐HAT) to generate carbon‐centered radicals, which subsequently undergo selective radical–radical coupling with p ‐QMs to form the diarylmethane framework.

European Journal of Organic ChemistryVol. 28(48)
Hubei University of Medicine (CN), Sichuan University (CN), West China Hospital of Sichuan University (CN), Ministry of Education (KR), Taihe Hospital (CN)
Openalex Percentile: Top 74%
Synthesis of Indole Derivatives
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