Synthesis of 1,2-Diketones via a Metal-Free, Visible-Light-Induced Aerobic Photooxidation of Alkynes

1,2-Diketones were synthesized by the oxidation of corresponding alkynes using air as the oxidant under metal-free conditions upon irradiation of blue light. A cheap and readily available organic dye, eosin Y, was used as the photocatalyst. For various substituents on the aryl ring, the reaction pro...

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Veröffentlicht in:Journal of organic chemistry 2016-08, Vol.81 (16), p.7256-7261
Hauptverfasser: Liu, Xu, Cong, Tiantian, Liu, Ping, Sun, Peipei
Format: Artikel
Sprache:eng
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Zusammenfassung:1,2-Diketones were synthesized by the oxidation of corresponding alkynes using air as the oxidant under metal-free conditions upon irradiation of blue light. A cheap and readily available organic dye, eosin Y, was used as the photocatalyst. For various substituents on the aryl ring, the reaction proceeded smoothly to give the dicarbonylation products in moderate to good yields. Some oxidation-sensitive groups, such as formyl and the carbon–carbon double bond, were tolerated under the developed reaction conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00097