通过电化学Appel反应合成腈

doi:10.6023/cjoc202202007

有机化学 ›› 2022, Vol. 42 ›› Issue (7): 2229-2235.DOI: 10.6023/cjoc202202007 上一篇下一篇

研究论文

通过电化学Appel反应合成腈

李海琼, 尹梦云, 谢芬芬, 张正兵^*(), 韩盼^*(), 敬林海^*()

西华师范大学化学化工学院化学合成与污染控制四川省重点实验室四川南充 637002

收稿日期:2022-02-06 修回日期:2022-03-11 发布日期:2022-08-09
通讯作者: 张正兵, 韩盼, 敬林海
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22001217); 四川省科技厅(2021ZYD0064); 西华师范大学英才基金(17YC020); 西华师范大学基本科研业务费(19D037); 西华师范大学基本科研业务费(19E034)

Synthesis of Nitrile via Electrochemical Appel Reaction

Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang(), Pan Han(), Linhai Jing()

Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, Sichuan 637002

Received:2022-02-06 Revised:2022-03-11 Published:2022-08-09
Contact: Zhengbing Zhang, Pan Han, Linhai Jing
About author:
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22001217); Science and Technology Program of Sichuan Province(2021ZYD0064); Meritocracy Research Funds of China West Normal University(17YC020); Fundamental Research Funds of China West Normal University(19D037); Fundamental Research Funds of China West Normal University(19E034)

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摘要/Abstract

探索了一种通过电化学Appel反应合成腈的方法. 该方法具有操作简单、反应条件温和、环境友好的优点, 可以合成一系列芳香腈和脂肪腈类化合物. 在循环伏安实验和控制实验基础上, 提出了电化学Appel反应机理用于解释反应过程.

关键词: 电化学合成, Appel反应, 肟的脱水, 腈的合成

An electrochemical Appel reaction was developed for the synthesis of nitriles. This protocol features operationally simplicity, mild reaction conditions and environmental friendliness, enabling synthesis of various aromatic and aliphatic nitriles. Based on the controlled experiments and cyclic voltammetry (CV) experimental results, an electrochemical Appel reaction mechanism was proposed to explain the reaction process.

Key words: electrochemical synthesis, Appel reaction, dehydration of oximes, synthesis of nitriles

引用此文

李海琼, 尹梦云, 谢芬芬, 张正兵, 韩盼, 敬林海. 通过电化学Appel反应合成腈[J]. 有机化学, 2022, 42(7): 2229-2235.

Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang, Pan Han, Linhai Jing. Synthesis of Nitrile via Electrochemical Appel Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2229-2235.

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Entry	Electrolyte	Solvent	Base	Yield^b/%
1	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	67
2^c	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	33
3^d	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	26
4^e	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	48
5	ⁿBu₄NBF₄	CH₃CN	NaHCO₃	41
6	Me₄NBF₄	CH₃CN	NaHCO₃	55
7	ⁿBu₄NClO₄	CH₃CN	NaHCO₃	60
8	LiClO₄	CH₃CN	NaHCO₃	11
9	TBAB	CH₃CN	NaHCO₃	85 (83)^f
10	TBAI	CH₃CN	NaHCO₃	60
11	TBAB	CH₃CN	Na₂CO₃	70
12	TBAB	CH₃CN	K₃PO₄	46
13	TBAB	CH₃CN	Cs₂CO₃	69
14	TBAB	CH₃CN	Et₃N	44
15	TBAB	THF	NaHCO₃	0
16	TBAB	DCM	NaHCO₃	48
17	TBAB	DMF	NaHCO₃	15
18	TBAB	Dioxane	NaHCO₃	0
19^g	TBAB	CH₃CN	NaHCO₃	64
20^h	TBAB	CH₃CN	NaHCO₃	57
21ⁱ	TBAB	CH₃CN	NaHCO₃	50
22^j	TBAB	CH₃CN	NaHCO₃	0

Entry	Electrolyte	Solvent	Base	Yield^b/%
1	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	67
2^c	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	33
3^d	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	26
4^e	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	48
5	ⁿBu₄NBF₄	CH₃CN	NaHCO₃	41
6	Me₄NBF₄	CH₃CN	NaHCO₃	55
7	ⁿBu₄NClO₄	CH₃CN	NaHCO₃	60
8	LiClO₄	CH₃CN	NaHCO₃	11
9	TBAB	CH₃CN	NaHCO₃	85 (83)^f
10	TBAI	CH₃CN	NaHCO₃	60
11	TBAB	CH₃CN	Na₂CO₃	70
12	TBAB	CH₃CN	K₃PO₄	46
13	TBAB	CH₃CN	Cs₂CO₃	69
14	TBAB	CH₃CN	Et₃N	44
15	TBAB	THF	NaHCO₃	0
16	TBAB	DCM	NaHCO₃	48
17	TBAB	DMF	NaHCO₃	15
18	TBAB	Dioxane	NaHCO₃	0
19^g	TBAB	CH₃CN	NaHCO₃	64
20^h	TBAB	CH₃CN	NaHCO₃	57
21ⁱ	TBAB	CH₃CN	NaHCO₃	50
22^j	TBAB	CH₃CN	NaHCO₃	0

通过电化学Appel反应合成腈

Synthesis of Nitrile via Electrochemical Appel Reaction

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