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

doi:10.6023/cjoc202012020

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2319-2325.DOI: 10.6023/cjoc202012020 Previous Articles Next Articles

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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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Abstract

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

Cite this article

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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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