Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 20, Pages 5777-5782Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802092
Keywords
continuous flow; cycloaddition; diazo compounds; esterification; hydrazones
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation
- Canada Research Chair Program
- FRQNT Centre in Green Chemistry and Catalysis (CGCC)
- Universite de Montreal
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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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