Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide

doi:10.6023/cjoc202104021

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3668-3674.DOI: 10.6023/cjoc202104021 Previous Articles Next Articles

Special Issue: 镍催化有机反应虚拟合辑

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非均相含镍层状双金属氧化物催化异色满与芳伯胺的高效氧化偶联

钱俊峰, 田晓婷, 吴中, 姚杰, 王慧, 周维友^*()

常州大学石油化工学院江苏省绿色催化材料与技术重点实验室江苏常州 213164

收稿日期:2021-04-10 修回日期:2021-06-07 发布日期:2021-06-17
通讯作者: 周维友
基金资助:
江苏省绿色催化材料与技术重点实验室基金(BM2012110); 江苏省高等学校自然科学研究重大项目(20KJA530003); 江苏省生物质能源与材料重点实验室基金(JSBEM202018)

Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide

Junfeng Qian, Xiaoting Tian, Zhong Wu, Jie Yao, Hui Wang, Weiyou Zhou()

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Changzhou University, Changzhou, Jiangsu 213164

Received:2021-04-10 Revised:2021-06-07 Published:2021-06-17
Contact: Weiyou Zhou
Supported by:
Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology(BM2012110); Natural Science Foundation for Colleges and Universities in Jiangsu Province(20KJA530003); Jiangsu Key Laboratory of Biomass Energy and Material(JSBEM202018)

An efficient heterogeneous catalytic system based on NiGa layered double oxide (Ni₃Ga-LDO) for the C—N coupling between isochroman and primary arylamines has been described. Various primary arylamines were tolerated by the catalytic system, and good to excellent yields for the corresponding coupled products could be obtained. The results indicated that Ni species played the key role in the oxidative cross-coupling process, and the catalyst had good catalytical and structural stability. The protocol provides an effective alternative approach to construct C—N bond.

Key words: oxidative coupling, isochroman, primary arylamine, NiGa layered double oxide, C—N construction

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Junfeng Qian, Xiaoting Tian, Zhong Wu, Jie Yao, Hui Wang, Weiyou Zhou. Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3668-3674.

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Fig. & Tab. 5

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非均相含镍层状双金属氧化物催化异色满与芳伯胺的高效氧化偶联

Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide

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Entry	Catalyst	Solvent	Oxidant	2a/1	Temp./℃	Conv.^b/%	Sel.^b/%
1	Ni₃Ga-LDH	Toluene	TBHP	1	80	42	50
2	Ni₃Ga-LDO	Toluene	TBHP	1	80	65	58
3	Ni₃Al-LDO	Toluene	TBHP	1	80	60	34
4	Ni₃In-LDO	Toluene	TBHP	1	80	44	25
5	Ni₃Ga-LDO	Acetonitrile	TBHP	1	80	80	28
6	Ni₃Ga-LDO	Dioxane	TBHP	1	80	79	37
7	Ni₃Ga-LDO	Methanol	TBHP	1	80	60	28
8	Ni₃Ga-LDO	H₂O	TBHP	1	80	Trace	—
9	Ni₃Ga-LDO	DMSO	TBHP	1	80	Trace	—
10	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	1	80	73	60
11	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	DTBP	1	80	Trace	—
12	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	Na₂S₂O₈	1	80	Trace	—
13	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	O₂	1	80	Trace	—
14	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	2	80	77	70
15	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	4	80	82	48
16	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	2	60	60	40
17	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	2	100	72	64
18^c	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	2	80	82	75
19^d	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	2	80	94	34
20^c^,^e	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	2	80	86	77
21^c^,^f	Ni₃Ga-LDO	1,1,2,2-Tetrachloroethane	TBHP	2	80	92	70

Entry	Catalyst	Additive	Conv.^b/%	Sel.^b/%
1	Ni₃Ga-LDO	—	86	77
2	—	—	52	38
3^c	Ni₃Ga-LDO (air)	—	79	13
4	Mg₃Ga-LDO	—	Trace	—
5^d	Ni₂(AcO)₂	—	76	39
6	Ni₃Ga-LDO	BHT^e	13	63
7	Ni₃Ga-LDO	TEMPO^e	82	52