Journal
CHEMICAL SCIENCE
Volume 10, Issue 13, Pages 3802-3806Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc05558k
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC) [RGPIN-06438]
- Canada Foundation for Innovation Leaders Opportunity Funds [227346]
- Canada Research Chair Program [CRC-227346]
- FRQNT Centre in Green Chemistry and Catalysis (CGCC) Strategic Cluster [RS-171310]
- Universite de Montreal
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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.
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