Visible-Light-Driven Synthesis of Dihydroaurones from Aromatic Diazo Compounds

Dihydroaurones, which are derivatives of aurones, exhibit similar biological activity. Although there are many synthetic methods for dihydroaurones, ecofriendly methodologies that circumvent the use of precious metals still need to be explored. In this work, a catalyst-free, visible-light-driven synthesis of dihydroaurones has been developed through the cyclization of aromatic diazo compounds. The reaction proceeded smoothly under mild conditions, resulting in a series of dihydroaurones in moderate to high yields. Mechanistic investigation suggests that this process involves a radical-pair Stevens rearrangement.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-06
DOI
https://doi.org/10.1021/acs.joc.4c01064
Citations
6
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
1.50

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article

Visible-Light-Driven Synthesis of Dihydroaurones from Aromatic Diazo Compounds

Guojun Zheng, Gang Xiao, Xiuyuan Duan
6 citations
The Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
1.50
article

Visible-Light-Driven Synthesis of Dihydroaurones from Aromatic Diazo Compounds

Guojun Zheng, Gang Xiao, Xiuyuan Duan
article en
6 citations

Abstract

Dihydroaurones, which are derivatives of aurones, exhibit similar biological activity. Although there are many synthetic methods for dihydroaurones, ecofriendly methodologies that circumvent the use of precious metals still need to be explored. In this work, a catalyst-free, visible-light-driven synthesis of dihydroaurones has been developed through the cyclization of aromatic diazo compounds. The reaction proceeded smoothly under mild conditions, resulting in a series of dihydroaurones in moderate to high yields. Mechanistic investigation suggests that this process involves a radical-pair Stevens rearrangement.

The Journal of Organic ChemistryVol. 89(18)
Beijing University of Chemical Technology (CN)
Beijing Municipal Natural Science Foundation, National Key Research and Development Program of China
Openalex Percentile: Top 19%
Cyclopropane Reaction Mechanisms
1.50
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