无金属条件下叔丁基亚磺酰胺衍生物在B2pin2/D2O体系中的氘代还原

doi:10.6023/cjoc202012020

有机化学 ›› 2021, Vol. 41 ›› Issue (6): 2319-2325.DOI: 10.6023/cjoc202012020 上一篇下一篇

研究论文

无金属条件下叔丁基亚磺酰胺衍生物在B₂pin₂/D₂O体系中的氘代还原

李琳琳^a, 陈晓雨^a, 裴聪聪^a, 李敬亚^b, 邹大鹏^a^,^*(), 吴养洁^a^,^*(), 吴豫生^a^,^b^,^*()

a 郑州大学化学学院绿色催化中心郑州 450052
b 郑州泰基鸿诺医药股份有限公司郑州 450052

收稿日期:2020-12-12 修回日期:2021-03-02 发布日期:2021-03-22
通讯作者: 邹大鹏, 吴养洁, 吴豫生
基金资助:
国家自然科学基金(21172200); 国家自然科学基金(21702191)

Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B₂pin₂/D₂O System

Linlin Li^a, Xiaoyu Chen^a, Congcong Pei^a, Jingya Li^b, Dapeng Zou^a(), Yangjie Wu^a(), Yusheng Wu^a^,^b()

a College of Chemistry, Green Catalysis Center, Zhengzhou University, Zhengzhou 450052
b Tetranov Biopharm, Limited Liability Company, Zhengzhou 450052

Received:2020-12-12 Revised:2021-03-02 Published:2021-03-22
Contact: Dapeng Zou, Yangjie Wu, Yusheng Wu
Supported by:
National Natural Science Foundation of China(21172200); National Natural Science Foundation of China(21702191)

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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

引用此文

李琳琳, 陈晓雨, 裴聪聪, 李敬亚, 邹大鹏, 吴养洁, 吴豫生. 无金属条件下叔丁基亚磺酰胺衍生物在B₂pin₂/D₂O体系中的氘代还原[J]. 有机化学, 2021, 41(6): 2319-2325.

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.

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Entry	B₂pin₂ (equiv.)	Base (equiv.)	Solvent	Yield^b/%
1	B₂pin₂ (1.2)	K₃PO₄(1.0)	H₂O	33
2	B₂pin₂ (1.2)	KOH (1.0)	H₂O	Trace^c
3	B₂pin₂ (1.2)	NaOAc (1.0)	H₂O	ND^d
4	B₂pin₂ (1.2)	K₂CO₃ (1.0)	H₂O	64
5	B₂pin₂ (1.2)	Cs₂CO₃ (1.0)	H₂O	69
6	B₂pin₂ (1.2)	CsF (1.0)	H₂O	10
7	B₂pin₂ (1.2)	CsOAc (1.0)	H₂O	ND^d
8	B₂pin₂ (1.2)	Na₂CO₃ (1.0)	H₂O	62
9	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	H₂O	85
10	B₂pin₂ (1.2)	Cs₂CO₃ (1.5)	H₂O	78
11	B₂pin₂ (1.0)	Cs₂CO₃ (1.2)	H₂O	65
12	B₂pin₂ (1.5)	Cs₂CO₃ (1.2)	H₂O	69
13	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	DMF/H₂O (V∶V=1∶1)	56
14	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	Dioxane/H₂O (V∶V=1∶1)	33
15	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	MeOH/H₂O (V∶V=1∶1)	68
16	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	83 (91)
17^e	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O/H₂O (n∶n=1∶1)	88 (54)
18^f	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	93 (95)
19^f^,^g	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	93 (93)
20^f^,^h	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	93 (96)
21^f^,ⁱ^,^j	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	93 (98)

Entry	B₂pin₂ (equiv.)	Base (equiv.)	Solvent	Yield^b/%
1	B₂pin₂ (1.2)	K₃PO₄(1.0)	H₂O	33
2	B₂pin₂ (1.2)	KOH (1.0)	H₂O	Trace^c
3	B₂pin₂ (1.2)	NaOAc (1.0)	H₂O	ND^d
4	B₂pin₂ (1.2)	K₂CO₃ (1.0)	H₂O	64
5	B₂pin₂ (1.2)	Cs₂CO₃ (1.0)	H₂O	69
6	B₂pin₂ (1.2)	CsF (1.0)	H₂O	10
7	B₂pin₂ (1.2)	CsOAc (1.0)	H₂O	ND^d
8	B₂pin₂ (1.2)	Na₂CO₃ (1.0)	H₂O	62
9	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	H₂O	85
10	B₂pin₂ (1.2)	Cs₂CO₃ (1.5)	H₂O	78
11	B₂pin₂ (1.0)	Cs₂CO₃ (1.2)	H₂O	65
12	B₂pin₂ (1.5)	Cs₂CO₃ (1.2)	H₂O	69
13	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	DMF/H₂O (V∶V=1∶1)	56
14	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	Dioxane/H₂O (V∶V=1∶1)	33
15	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	MeOH/H₂O (V∶V=1∶1)	68
16	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	83 (91)
17^e	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O/H₂O (n∶n=1∶1)	88 (54)
18^f	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	93 (95)
19^f^,^g	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	93 (93)
20^f^,^h	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	93 (96)
21^f^,ⁱ^,^j	B₂pin₂ (1.2)	Cs₂CO₃ (1.2)	D₂O	93 (98)

无金属条件下叔丁基亚磺酰胺衍生物在B₂pin₂/D₂O体系中的氘代还原

Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B₂pin₂/D₂O System

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