4.8 Article

Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation

期刊

CHEMICAL SCIENCE
卷 10, 期 13, 页码 3802-3806

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc05558k

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资金

  1. Natural Science and Engineering Research Council of Canada (NSERC) [RGPIN-06438]
  2. Canada Foundation for Innovation Leaders Opportunity Funds [227346]
  3. Canada Research Chair Program [CRC-227346]
  4. FRQNT Centre in Green Chemistry and Catalysis (CGCC) Strategic Cluster [RS-171310]
  5. Universite de Montreal

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Electron-rich alkyl diazo compounds are powerful reagents in organic synthesis, but the risks associated with their toxicity and instability often limit their uses. Herein we describe an efficient, easy-to-handle and safe batch protocol for the in situ generation and cyclopropanation of these highly reactive non-stabilized diazoalkanes through the oxidation of free hydrazones using iodosylbenzene. Numerous substituted cyclopropanes have been synthesized using this methodology, including various gem-dimethylcyclopropanes of particular interest in medicinal chemistry.

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