Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology. (19th April 2018)

• Record Type: Journal Article
• Authors: Rullière, Pauline; Benoit, Guillaume; Allouche, Emmanuelle M. D.; Charette, André B.
• Is Part Of: Angewandte Chemie. Volume 130:Number 20(2018)
• Page Start: 5879
• Page End: 5884
• Publication Date: 2018-04-19
• Subjects: Cycloadditionen -- Diazoverbindungen -- Flusschemie -- Hydrazone -- Veresterungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201802092
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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.