4.8 Article

Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 20, 页码 5777-5782

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802092

关键词

continuous flow; cycloaddition; diazo compounds; esterification; hydrazones

资金

  1. Natural Science and Engineering Research Council of Canada (NSERC)
  2. Canada Foundation for Innovation
  3. Canada Research Chair Program
  4. FRQNT Centre in Green Chemistry and Catalysis (CGCC)
  5. Universite de Montreal

向作者/读者索取更多资源

Despite the high synthetic potential of nonstabilized diazo compounds, their utilization has always been hampered by stability, toxicity, and safety issues. The present method opens up access to the most reactive nonstabilized diazoalkanes. Among diazo compounds, nonstabilized alkyl diazo compounds are the least represented because of their propensity to degrade during preparation. The continuous flow oxidation process of hydrazones on a silver oxide column afforded an output stream of base- and metal-free pure diazo solution in dichloromethane. Starting from innocuous ketones and aldehydes, this methodology allows the production of a broad range of unprecedented diazoalkanes compounds in excellent yields, while highlighting their synthetic potential and the possibility of safe large-scale diazo production.

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