Chinese Journal of Organic Chemistry >
Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B2pin2/D2O System
Received date: 2020-12-12
Revised date: 2021-03-02
Online published: 2021-03-22
Supported by
National Natural Science Foundation of China(21172200); National Natural Science Foundation of China(21702191)
A transition metal-free deuteride reduction protocol of N-tert-butanesulfinyl ketimines with B2pin2 has been developed. After screening of reaction parameters, such as base, solvent, and the amount of B2pin2, a series of deuterated secondary amines were obtained in reasonable yields with excellent deuterium purity by using D2O as the deuterium source. Mild reaction conditions, operational simplicity, and easily scaled up to gram scale are the considerable advantages of this methodology. After deprotection of tert-butanesulfinyl, cyclopentan-1-d-amine is obtained in high yield.
Linlin Li , Xiaoyu Chen , Congcong Pei , Jingya Li , Dapeng Zou , Yangjie Wu , Yusheng Wu . Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B2pin2/D2O System[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2319 -2325 . DOI: 10.6023/cjoc202012020
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