无金属参与的电化学促进2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)介导的环胺α-氰化和膦酰化反应

doi:10.6023/cjoc202103049

有机化学 ›› 2021, Vol. 41 ›› Issue (8): 3223-3234.DOI: 10.6023/cjoc202103049 上一篇下一篇

所属专题：有机电合成虚拟专辑

研究论文

无金属参与的电化学促进2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)介导的环胺α-氰化和膦酰化反应

高君青^a, 翁信军^b, 马聪^b, 徐学涛^a^,^*(), 方萍^b^,^*(), 梅天胜^b^,^*()

a 五邑大学生物科技与大健康学院广东江门 529020
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室分子合成卓越中心上海 200032

收稿日期:2021-03-26 修回日期:2021-04-26 发布日期:2021-05-14
通讯作者: 徐学涛, 方萍, 梅天胜
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21772222); 国家自然科学基金(21821002); 广东省教育厅基金(2017KSYS010); 广东省教育厅基金(2017KZDXM084); 广东省教育厅基金(2019KZDZX2003); 广东省教育厅基金(2019KZDXM035)

Electrochemical 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO)-Mediated α-Cyanation and Phosphonylation of Cyclic Amines with Metal-Free Conditions

Junqing Gao^a, Xinjun Weng^b, Cong Ma^b, Xuetao Xu^a(), Ping Fang^b(), Tiansheng Mei^b()

a School of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020
b Center for Excellence in Molecular Synthesis, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2021-03-26 Revised:2021-04-26 Published:2021-05-14
Contact: Xuetao Xu, Ping Fang, Tiansheng Mei
About author:
† (These authors contributed equally to this work).
Supported by:
National Natural Science Foundation of China(21772222); National Natural Science Foundation of China(21821002); Department of Education of Guangdong Province(2017KSYS010); Department of Education of Guangdong Province(2017KZDXM084); Department of Education of Guangdong Province(2019KZDZX2003); Department of Education of Guangdong Province(2019KZDXM035)

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摘要/Abstract

探究了无金属电化学氧化氰化和膦酸酯基化反应, 其中2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)降低了底物的电极电位, 避免了某些富电子芳香胺在电化学条件下的过氧化反应. 该方法具有良好的官能团兼容性, 是在温和条件下合成α-氨基腈和α-氨基膦酸酯的一种有效且实用的方法, 通过研究表明产物通过Shono氧化形成亚胺物种来实现的.

关键词: 电化学, Shono氧化, 氰基化, 膦酸酯基化

Metal-free electrochemical oxidation cyanation and phosphonylation reactions had been developed, in which 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO) reduced the electrode potential of substrate and avoided over oxidation of some electron rich aromatic amines under electrochemical conditions. This protocol had good functional group compatibility, which made it to be a practical and efficient method to synthesize α-aminonitriles and α-amino phosphonates under mild conditions. Preliminary study indicated that the formation of the product was through the Shono oxidation of imine species.

Key words: electrochemistry, Shono oxidation, cyanation, phosphonylation

引用此文

高君青, 翁信军, 马聪, 徐学涛, 方萍, 梅天胜. 无金属参与的电化学促进2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)介导的环胺α-氰化和膦酰化反应[J]. 有机化学, 2021, 41(8): 3223-3234.

Junqing Gao, Xinjun Weng, Cong Ma, Xuetao Xu, Ping Fang, Tiansheng Mei. Electrochemical 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO)-Mediated α-Cyanation and Phosphonylation of Cyclic Amines with Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3223-3234.

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图/表 8

Scheme 1. Synthesize of α-aminonitriles

Entry	Variation from standard conditions	Yield^b/%
1	None	99 (97)^c
2	4-CN-TEMPO instead of TEMPO	71
3	4-COOH-TEMPO instead of TEMPO	48
4	ABNO instead of TEMPO	67
5	PhCO₂ABNO instead of TEMPO	42
6	Keto-ABNO instead of TEMPO	33
7	TBAOAc instead of TBAPF₆	46
8	TBAClO₄ instead of TBAPF₆	53
9	NaClO₄ instead of TBAPF₆	68
10	H₂O instead of CF₃CH₂OH	69
11	HFIP instead of CF₃CH₂OH	91
12	MeOH instead of CF₃CH₂OH	78
13	Isopropanol instead of CF₃CH₂OH	38
14	No current	N.R.
15	No TEMPO, no CH₃CH₂OH	29
16	No TEMPO	45

Table 1. Optimization of reaction conditionsa

Table 2. Substrate scope of cyanationa

Table 3. Substrate scope of phosphonylationa

Scheme 2. Gram-scale experiment

Scheme 3. Comparison experiments

Figure 1. Cyclic voltammograms (0.1 V/s) Recorded on a Pt electrode (area=0.03 cm2) in CH3CN (10 mL) and TBAPF6 (0.1 mol/L) of TEMPO (5 mmol/L) (black line); N-phenyl pyrrolidine (1a, 5 mmol/L) (red line); N-phenyl pyrrolidine (1a, 5 mmol/L) and TEMPO (5 mmol/L) (blue line)

Scheme 4. Proposed mechanistic pathway

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无金属参与的电化学促进2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)介导的环胺α-氰化和膦酰化反应

Electrochemical 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO)-Mediated α-Cyanation and Phosphonylation of Cyclic Amines with Metal-Free Conditions

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