摘要/Abstract

利用廉价易得的氘代试剂D₂O作为氘源,在无金属条件下实现了叔丁基亚磺酰胺类衍生物与B₂pin₂(联硼酸频那醇酯)的氘代还原反应. 通过对碱、溶剂、B₂pin₂的用量等进行筛选,在较优的反应条件下以中等到较好的收率得到了一系列相应的氘代二级胺. 该方法反应条件温和,操作简单,放大到克级规模也不影响反应收率. 通过脱除N-叔丁基亚磺酰基, 能以较高的收率得到环戊烷-1-d-1-胺.
关键词: 氘代还原, 叔丁基亚磺酰胺类衍生物, 联硼酸频那醇酯, 氘代二级胺
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.
Key words: deuteride reduction, N-tert-butanesulfinyl ketimines, bis(pinacolate)diboron, deuterated secondary amines


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