4.6 Article

Organoselenium-Catalyzed Oxidative Ring Expansion of Methylenecyclopropanes with Hydrogen Peroxide

Journal

CHEMCATCHEM
Volume 8, Issue 6, Pages 1033-1037

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201501309

Keywords

green chemistry; methylenecyclopropanes; selectivity control; selenium; small ring systems

Funding

  1. National Natural Science Foundation of China (NNSFC) [21202141, 21173182]
  2. Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions
  3. Yangzhou Nature Science Foundation [YZ2014040]
  4. Opening Foundation of the Key Laboratory of Environmental Materials and Engineering of Jiangsu Province [K14010]
  5. Open Project Program of Jiangsu Key Laboratory of Zoonosis [R1509]

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Catalyst screening and optimization of reaction conditions allowed control of the organoselenium-catalyzed oxidative ring expansion of highly active methylenecyclopropanes to give substituted cyclobutanones selectively. This protocol employs H2O2 as a clean oxidant and generates no waste and, therefore, provides green access to useful, but not readily available, substituted cyclobutanones under mild conditions.

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