Chinese Journal of Organic Chemistry >
Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt
Received date: 2021-11-07
Revised date: 2022-02-07
Online published: 2022-02-25
Supported by
Program for Changjiang Scholars and Innovative Research Team in University(IRT17R94); Natural Science Foundation of China(21762046); Natural Science Foundation of China(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 and the Program for the “Young Talent” in Yunnan University
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%~93% yields through a reaction sequence of nucleophilic addition/proton migration/nucleophilic substitution and deselenization of β-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.
Fei Yuan , Yan Zhao , Qingsong Guo , Fudan Yin , Jinrong Lai , Beifang Nian , Ming Zhang , E Tang . Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1759 -1769 . DOI: 10.6023/cjoc202111015
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