Gold-Catalyzed Selective Oxidation of 1,3-Diynamides to Access 4-Oxo-but-2-ynamides

doi:10.6023/cjoc202007019

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 376-383.DOI: 10.6023/cjoc202007019 Previous Articles Next Articles

Special Issue: 热点论文虚拟合集

Article

金催化选择性氧化共轭炔基炔酰胺合成4-羰基丁-2-炔酰胺

万万^a, 刘继兵^a, 黄学良^a^,^*()

a 中国科学院福建物质结构研究所中国科学院大学煤制乙二醇及相关技术中科院重点实验室福州 350002

收稿日期:2020-07-06 修回日期:2020-08-04 发布日期:2020-08-19
通讯作者: 黄学良
作者简介:
* Corresponding author. E-mail: huangxl@fjirsm.ac.cn
基金资助:
国家自然科学基金(21871259); 国家自然科学基金(2191244); 中国科学院战略性先导科技专项B类(XDB20000000)

Gold-Catalyzed Selective Oxidation of 1,3-Diynamides to Access 4-Oxo-but-2-ynamides

Wan Wan^a, Jibing Liu^a, Xueliang Huang^a^,^*()

a Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350002

Received:2020-07-06 Revised:2020-08-04 Published:2020-08-19
Contact: Xueliang Huang
Supported by:
the National Natural Science Foundation of China(21871259); the National Natural Science Foundation of China(2191244); the Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000)

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Abstract

A gold-catalyzed selective oxidation of 1,3-diynamides has been developed to provide a novel approach to 4-oxo-but-2-ynamides. The products possess activated C—C triple bond, and often serve as versatile building blocks in synthetic community. This gold-catalyzed selective oxidation of 1,3-diynamides to provide 4-oxo-but-2-ynamides is noteworthy, since the traditional 1,2-dicarbonyl type products were not observed. Under standard conditions, a range of 4-oxo-but-2-yna- mide derivatives were obtained in moderate to high yields.

Key words: 3-diynamides, gold catalysis, selective oxidation, dicarbonyl compounds

Cite this article

Wan Wan, Jibing Liu, Xueliang Huang. Gold-Catalyzed Selective Oxidation of 1,3-Diynamides to Access 4-Oxo-but-2-ynamides[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 376-383.

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References 10

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金催化选择性氧化共轭炔基炔酰胺合成4-羰基丁-2-炔酰胺

Gold-Catalyzed Selective Oxidation of 1,3-Diynamides to Access 4-Oxo-but-2-ynamides

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Entry	Variation from standard condition	Time/h	Yield ^b /%
1	—	1.5	85
2	Oxidant (R=H)	10	trace
3	Oxidant (R=Br)	6	63
4	Oxidant (R=Me)	7	trace
5	Quinoline- N-oxide as oxidant	5	19
6	DMSO as oxidant	22	21
7	Diphenyl sulfoxide as oxidant	22	72
8	JohnphosAuNTf ₂as catalyst	2	19
9	JohnphosAuOMs as catalyst	9	46
10	BrettphosAu(MeCN)SbF ₆ as catalyst	2	78
11	^t BuXphosAu(MeCN)SbF ₆ as catalyst	8	55
12	Cu(OTf) ₂ as catalyst	5.5	40
13	Zn(OTf) ₂ as catalyst	6	8
14	AgOTf as catalyst	3	30
15	DCE as solvent	2	73
16	THF as solvent	15	32
17	React at 30 ℃	9	85
18	React at 60 ℃	2	85