4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 16, Pages 7256-7261

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00097

Keywords

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Funding

  1. National Natural Science Foundation of China [21272117, 21502097]
  2. Key International (Regional) Joint Research Program of NSFC [21420102002]
  3. Natural Science Foundation of the Education Department of Jiangsu province [15KJB150015]
  4. Priority Academic Program Development of Jiangsu Higher Education Institutions

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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.

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