Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water

doi:10.6023/cjoc202111010

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4712-4717.DOI: 10.6023/cjoc202111010 Previous Articles Next Articles

Special Issue: 有机电合成虚拟专辑；绿色合成化学专辑；热点论文虚拟合集

ARTICLES

α-酮酸、异腈和水的电化学三组分合成α-酮酰胺

吴红谕^a, 于贤勇^b^,^*(), 曹忠^a^,^*()

a 长沙理工大学化学化工学院电力与交通材料保护湖南省重点实验室&细胞化学湖南省重点实验室长沙 410114
b 湖南科技大学化学化工学院理论有机化学与功能分子教育部重点实验室湖南湘潭 411201

收稿日期:2021-11-04 修回日期:2021-12-09 发布日期:2021-12-15
通讯作者: 于贤勇, 曹忠
基金资助:
国家自然科学基金(21545010); 湖南省自然科学基金(2020JJ4599); 湖南省科技创新计划(2021RC5028)

Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water

Hongyu Wu^a, Xianyong Yu^b(), Zhong Cao^a()

a Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Hunan Provincial Key Laboratory of Cytochemistry, School of Chemistry and Chemical Engineering, Changsha University of Science and Technology, Changsha 410114
b Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201

Received:2021-11-04 Revised:2021-12-09 Published:2021-12-15
Contact: Xianyong Yu, Zhong Cao
Supported by:
National Natural Science Foundation of China(21545010); Natural Science Foundation of Hunan Province(2020JJ4599); Science and Technology Innovation Program of Hunan Province(2021RC5028)

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Abstract

Electrochemical organic synthesis is considered as an environmentally benign method because it employs traceless electrons as redox agents, thereby avoiding the need for chemical oxidants. The electrochemical decarboxylative acylation of isocyanides and relay hydration reaction for the synthesis of α-ketoamides was developed. This reaction can be carried out under mild conditions in the absence of a chemical oxidant and a transition-metal catalyst.

Key words: electrochemical synthesis, decarboxylative acylation, hydration reaction, isocyanide, α-ketoamides

Cite this article

Hongyu Wu, Xianyong Yu, Zhong Cao. Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4712-4717.

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References 15

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Entry	Variation from the standard reaction conditions	Yield^b/%
1	None	86
2	RVC(+)\|Al(–) instead of RVC(+)\|Pt(–)	74
3	RVC(+)\|Ag(–) instead of RVC(+)\|Pt(–)	78
4	RVC(+)\|RVC (–) instead of RVC(+)\|Pt(–)	73
5	Pt(+)\|Pt(–) instead of RVC(+)\|Pt(–)	80
6	C(+)\|Pt(–) instead of Pt(+)\|Pt(–)	81
7	NH₄I instead of KI	64
8	ⁿBu₄NI instead of KI	79
9	LiBF₄ instead of KI	N.R.
10	ⁿBu₄NBF₄ instead of KI	N.R.
11	Et₄NClO₄ instead of KI	N.R.
12	LiClO₄ instead of KI	N.R.
13	KI (10 mol%) instead of KI (20 mol%), 12 h	23
14	HFIP/H₂O instead of MeCN/H₂O	70
15	DMF/H₂O instead of MeCN/H₂O	26
16	THF/H₂O instead of MeCN/H₂O	21
17	DMSO/H₂O instead of MeCN/H₂O	Trace
18	EtOH/H₂O instead of MeCN/H₂O	Trace
19	DMA/H₂O instead of MeCN/H₂O	Trace
20	MeCN/H₂O=8 mL/1 mL	76
21	MeCN/H₂O=8 mL/3 mL	80
22	10 mA instead of 6 mA, 12 h	34
23	3 mA instead of 6 mA, 12 h	81
24	No electricity	N.R.
25	Under N₂ atmosphere	87

Entry	Variation from the standard reaction conditions	Yield^b/%
1	None	86
2	RVC(+)\|Al(–) instead of RVC(+)\|Pt(–)	74
3	RVC(+)\|Ag(–) instead of RVC(+)\|Pt(–)	78
4	RVC(+)\|RVC (–) instead of RVC(+)\|Pt(–)	73
5	Pt(+)\|Pt(–) instead of RVC(+)\|Pt(–)	80
6	C(+)\|Pt(–) instead of Pt(+)\|Pt(–)	81
7	NH₄I instead of KI	64
8	ⁿBu₄NI instead of KI	79
9	LiBF₄ instead of KI	N.R.
10	ⁿBu₄NBF₄ instead of KI	N.R.
11	Et₄NClO₄ instead of KI	N.R.
12	LiClO₄ instead of KI	N.R.
13	KI (10 mol%) instead of KI (20 mol%), 12 h	23
14	HFIP/H₂O instead of MeCN/H₂O	70
15	DMF/H₂O instead of MeCN/H₂O	26
16	THF/H₂O instead of MeCN/H₂O	21
17	DMSO/H₂O instead of MeCN/H₂O	Trace
18	EtOH/H₂O instead of MeCN/H₂O	Trace
19	DMA/H₂O instead of MeCN/H₂O	Trace
20	MeCN/H₂O=8 mL/1 mL	76
21	MeCN/H₂O=8 mL/3 mL	80
22	10 mA instead of 6 mA, 12 h	34
23	3 mA instead of 6 mA, 12 h	81
24	No electricity	N.R.
25	Under N₂ atmosphere	87

α-酮酸、异腈和水的电化学三组分合成α-酮酰胺

Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water

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