4.7 Article

Visible-Light Mediated Diarylselenylative Cyclization of 1,6-Enynes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 1, Pages 1273-1280

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02529

Keywords

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Funding

  1. National Natural Science Foundation of China [21702179]
  2. Priority Academic Program Development of Jiangsu Higher Education Institutions
  3. Natural Science Foundation of the Jiangsu Higher Education Institutions of China [17KJB150042]
  4. Lvyangjinfeng Talent Program of Yangzhou

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This study describes a selenylative cyclization reaction using diselenides as radical sources, with visible light irradiation generating selenium atom radical to trigger radical addition/cyclization/selenation sequences. Both terminal alkyne and internal alkyne derived 1,6-enynes were suitable for the synthetic protocol, leading to good yields of various selenium-containing cycles.
We herein described a selenylative cyclization reaction of enynes by the utilization of diselenides as radical sources. The visible-light irradiation of the reaction mixture enables the generation of the selenium atom radical to trigger the radical addition/cyclization/selenation sequences. Both terminal alkyne and internal alkyne derived 1,6-enynes were tested and suitable for the current synthetic protocol, delivering various kinds of selenium-containing cycles in good yields.

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