Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation. Issue 13 (4th March 2019)

• Record Type: Journal Article
• Authors: Allouche, Emmanuelle M. D.; Charette, André B.
• Is Part Of: Chemical science. Volume 10:Issue 13(2019)
• Page Start: 3802
• Page End: 3806
• Publication Date: 2019-03-04
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8sc05558k
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Highly reactive non-stabilized diazo compounds are generated from free hydrazones using iodosylbenzene. In situ MIRC cyclopropanations were performed on a wide array of substrates. Abstract : 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.