Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 42, Issue 6, Pages 1759-1769Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202111015
Keywords
high valent selenium salt; 1-(1-(amino)cyclopropyl)ketones; one-pot method; tandem reaction
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Funding
- Program for Changjiang Scholars and Innovative Research Team in University [IRT17R94]
- Natural Science Foundation of China [21762046, 22161050]
- Program for Yunnan Provincial Department of Science and Technology-Yunnan University Double First-Class Construction Joint Fund [2018FY001]
- Innovative Research Team (in Science and Technology) in University of Yunnan Province
- Program for the Young Talent in Yunnan University
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A new one-pot method for the efficient synthesis of 1-(1-(amino)cyclopropyl)ketone compounds has been developed. This method features mild reaction conditions, simple experiment operation, and good functional group compatibility.
A new one-pot method for the efficient synthesis of 1-(1-(amino)cyclopropyl)ketone compounds has been developed. Under the mediation of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1-(1-(amino)cyclopropyl)ketones were obtained in 70%similar to 93% yields through a reaction sequence of nucleophilic addition/proton migration/nucleophilic substitution and deselenization of beta-amino ketones and methyl phenyl vinyl selenium tetrafluoroborate. This method features mild reaction conditions, simple experiment operation, good functional group compatibility. Diphenyl diselenide, the general substrate of the selenium salt reagents, can be prepared by the simple treatment of the by-product methyl phenyl selenide with bromine and hydrazine. Therefore, the vinylselenide salts can be regenerated and reused, which improves the utilization of high-valent selenium reagents and improves the industrial application of this method.
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