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Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology
Author(s) -
Rullière Pauline,
Benoit Guillaume,
Allouche Emmanuelle M. D.,
Charette André B.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201802092
Subject(s) - diazo , chemistry , dichloromethane , alkyl , combinatorial chemistry , flow chemistry , continuous flow , organic chemistry , catalysis , solvent , biochemical engineering , engineering
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.