4.7 Article

N-Iodosuccinimide-Initiated Spirocyclopropanation of Styrenes with 1,3-Dicarbonyl Compound for the Synthesis of Spirocyclopropanes

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JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 15, 页码 6546-6553

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01163

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  1. National Natural Science Foundation of China [21102071, 21472082]
  2. Jiangsu 333 program
  3. Changzhou Jin-Feng-Huang program

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Herein is reported an N-iodosuccinimide-initiated spirocyclopropanation reaction of styrenes with 1,3-dicarbonyl compounds in the presence of white LED light. The reaction proceeds via two C-H and two C-I bond cleavage event, along with two C-C bond formation event, and formation of quaternary centers. These reactions could be carried out at room temperature and tolerated a wide range of substrates, resulting in good to excellent chemical yields. This developed radical reaction provides easy and practical access to spiro[2.4]heptane-4,7-dione derivatives.

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