Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 6, Pages 4263-4272Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c03100
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Funding
- National Natural Science Foundation of China [22078084, 51874132]
- Scientific Research Fund of Hunan Provincial Education Department [20A224]
- Science and Technology Planning Project of Hunan Province [2020RC3056, 2018TP1017]
- Natural Science Foundation of Hunan Province [2020JJ5221, 2020JJ5212]
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Heterocyclic compounds, especially oxygen-containing heterocyclic compounds, play a crucial role in bioactive compounds and drug leads. This study presents a visible-light-induced dual acylation reaction of alkenes to construct 3-substituted chroman-4-ones, which involves a nitrogen-centered radical strategy for a radical tandem cyclization reaction through carbon-carbon bond cleavage of oxime esters. A series of 3-substituted chroman-4-ones were successfully prepared with high yields.
Heterocyclic compounds, especially oxygen-containing heterocyclic compounds, are crucial moieties in bioactive compounds and drug leads. Substituted chroman-4-ones are a kind of the most significant structural skeletons. Herein, we report a visible-light-induced dual acylation of alkenes for constructing 3-substituted chroman-4-ones, which undergoes a radical tandem cyclization reaction through carbon-carbon bond cleavage of oxime esters by a nitrogen-centered radical strategy. A series of 3-substituted chroman-4-ones were prepared with up to 86% yield.
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