4.8 Article

A simple ketone as an efficient metal-free catalyst for visible-light-mediated Diels-Alder and aza-Diels-Alder reactions

Journal

GREEN CHEMISTRY
Volume 21, Issue 8, Pages 1916-1920

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9gc00485h

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Funding

  1. Fonds der Chemischen Industrie (FCI, Liebig-Fellowship)
  2. Chinese Scholarship Council (CSC funding)

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Diels-Alder reactions are highly effective between electron-rich dienes and electron-poor dienophiles. However, these reactions with electron-rich dienophiles are limited and require forcing conditions. Based on this, an efficient metal-free homogeneous system has been developed for the Diels-Alder reactions between electron-rich dienophiles and dienes under visible-light conditions. Additionally, this catalyst has shown excellent reactivity for aza-Diels-Alder reactions. This simple catalyst is commercially available, non-toxic, and cheap and has shown excellent reactivity which is comparable to and in some cases even better than the reported metal-based catalysts. Finally, the mechanism of this reaction has been proposed based on the experimental evidence.

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