Palladium-Catalyzed Intramolecular Decarboxylative Allylic Amination of Aroyloxycarbamates

doi:10.6023/cjoc202104030

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3089-3096.DOI: 10.6023/cjoc202104030 Previous Articles Next Articles

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钯催化的芳酰氧基氨基甲酸酯的分子内脱羧烯丙基胺化反应

李晓颖, 李培贺, 王峥, 付辉, 戴啟谱^*()

北京理工大学化学与化工学院原子分子簇科学教育部重点实验室光电材料北京市重点实验室北京 100081

收稿日期:2021-04-15 修回日期:2021-05-15 发布日期:2021-06-02
通讯作者: 戴啟谱
基金资助:
北京理工大学优秀青年学者研究基金(3190012211808); 北京理工大学优秀青年学者研究基金(3190012331518); 北京理工大学优秀青年学者研究基金(3190012331523); 国家自然科学基金(21871026)

Palladium-Catalyzed Intramolecular Decarboxylative Allylic Amination of Aroyloxycarbamates

Xiaoying Li, Peihe Li, Zheng Wang, Hui Fu, Qipu Dai()

Beijing Key Laboratory of Photoelectronic/Electrophotonic, Key Laboratory of Cluster Science of Ministry of Education, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081

Received:2021-04-15 Revised:2021-05-15 Published:2021-06-02
Contact: Qipu Dai
Supported by:
Excellent Young Scholars Research Fund of Beijing Institute of Technology(3190012211808); Excellent Young Scholars Research Fund of Beijing Institute of Technology(3190012331518); Excellent Young Scholars Research Fund of Beijing Institute of Technology(3190012331523); National Natural Science Foundation of China(21871026)

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Abstract

Allylamine compounds are one of the important compounds in organic synthetic chemistry and pharmaceutical chemistry, the synthetic methods of which are concerned. Using aroyloxycarbamates as start material, which was prepared in situ by cheap and easy-available carboxylic acid and hydroxylamine, allylamine compounds were synthesized by decarboxylation in one step. The reaction conditions are mild and the substrate is generally applicable. Moreover, the reaction realized the synthesis of indole.

Key words: palladium-catalysis, aroyloxycarbamate, decarboxylation, allylic amination, allylamine

Cite this article

Xiaoying Li, Peihe Li, Zheng Wang, Hui Fu, Qipu Dai. Palladium-Catalyzed Intramolecular Decarboxylative Allylic Amination of Aroyloxycarbamates[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3089-3096.

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References 31

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Entry	Catalyst	Ligand	Solvent	T/℃	Yield^b/%
1	[Ir(cod)Cl]₂	XantPhos	MeCN	80	17
2	Pd(OAc)₂	XantPhos	MeCN	80	43
3	Pd(TFA)₂	XantPhos	MeCN	80	69
4	PdCl₂	XantPhos	MeCN	80	80
5	Pd(DPPF)Cl₂•CH₂Cl₂		MeCN	80	21
6	PdCl₂	L1	MeCN	80	12
7	PdCl₂	L2	MeCN	80	Trace
8	PdCl₂	XantPhos	Hexane	80	49
9	PdCl₂	XantPhos	Toluene	80	52
10	PdCl₂	XantPhos	THF	80	64
11	PdCl₂	XantPhos	DMF	80	75
12	PdCl₂	XantPhos	MeCN	100	65
13	PdCl₂	XantPhos	MeCN	90	70
14	PdCl₂	XantPhos	MeCN	70	65
15	PdCl₂	XantPhos	MeCN	60	62

Entry	Catalyst	Ligand	Solvent	T/℃	Yield^b/%
1	[Ir(cod)Cl]₂	XantPhos	MeCN	80	17
2	Pd(OAc)₂	XantPhos	MeCN	80	43
3	Pd(TFA)₂	XantPhos	MeCN	80	69
4	PdCl₂	XantPhos	MeCN	80	80
5	Pd(DPPF)Cl₂•CH₂Cl₂		MeCN	80	21
6	PdCl₂	L1	MeCN	80	12
7	PdCl₂	L2	MeCN	80	Trace
8	PdCl₂	XantPhos	Hexane	80	49
9	PdCl₂	XantPhos	Toluene	80	52
10	PdCl₂	XantPhos	THF	80	64
11	PdCl₂	XantPhos	DMF	80	75
12	PdCl₂	XantPhos	MeCN	100	65
13	PdCl₂	XantPhos	MeCN	90	70
14	PdCl₂	XantPhos	MeCN	70	65
15	PdCl₂	XantPhos	MeCN	60	62

钯催化的芳酰氧基氨基甲酸酯的分子内脱羧烯丙基胺化反应

Palladium-Catalyzed Intramolecular Decarboxylative Allylic Amination of Aroyloxycarbamates

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