Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds

doi:10.6023/cjoc202210033

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 1115-1123.DOI: 10.6023/cjoc202210033 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑；中国女科学家专辑

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Ir(III)催化新型三组分串联三氟乙氧基化反应并一锅法构建复杂酰胺化合物

曾成富^a, 何媛^b, 李清^a^,^*(), 董琳^b^,^*()

a 四川师范大学化学与材料科学学院成都 610066
b 四川大学华西药学院成都 610041

收稿日期:2022-10-27 修回日期:2022-12-30 发布日期:2023-02-06
通讯作者: 李清, 董琳
基金资助:
四川省科技计划(2021YFG0111); 国家自然科学基金(22107082); 四川省中央引导地方科技发展专项(2021ZYD0058)

Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds

Chengfu Zeng^a, Yuan He^b, Qing Li^a(), Lin Dong^b()

a College of Chemistry and Material Science, Sichuan Normal University, Chengdu 610066
b West China School of Pharmacy, Sichuan University, Chengdu 610041

Received:2022-10-27 Revised:2022-12-30 Published:2023-02-06
Contact: Qing Li, Lin Dong
Supported by:
Sichuan Science and Technology Program(2021YFG0111); National Natural Science Foundation of China(22107082); Sichuan Science and Technology Development under the Central Government(2021ZYD0058)

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Abstract

Ir(III)-catalyzed three-component cascade reaction to construct unique trifluoroethoxylation amide compounds has been developed, meanwhile the fluorinated compounds could continue to react with alcohols to prepare complex spiro isoindolinone derivatives in one-pot. The highly efficient approaches produce various amide compounds by condition- controlled.

Key words: three-component cascade reaction, fluorination, spirocyclization, 2-aryloxazole

Cite this article

Chengfu Zeng, Yuan He, Qing Li, Lin Dong. Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1115-1123.

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Fig. & Tab. 7

References 11

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Entry	Oxidant	Ag/Additive	Solvent	Yield^b/%
Entry	Oxidant	Ag/Additive	Solvent	3aa	3aa'
1	AgOAc	AgSbF₆	TFE	ND	ND
2	Cu(OAc)₂•H₂O	AgSbF₆	TFE	ND	ND
3	Cu(acac)₂	AgSbF₆	TFE	Trace	ND
4	Cu(OTf)₂	AgSbF₆	TFE	37	Trace
5	Cu(OTf)₂	AgNTf₂	TFE	40	Trace
6	Cu(OTf)₂	AgBF₄	TFE	44	Trace
7	Cu(OTf)₂	CH₃SO₃Ag	TFE	38	Trace
8	Cu(OTf)₂	AgOTf	TFE	47	Trace
9^c	Cu(OTf)₂	AgOTf	TFE	72	Trace
10^c	Cu(OTf)₂	AgOTf	MeOH	ND	ND
11^c	Cu(OTf)₂	AgOTf	EtOH	ND	ND
12^c	Cu(OTf)₂	AgOTf	DCE	ND	ND
13^c	Cu(OTf)₂	AgOTf	CCl₃CH₂OH	ND	ND
14^c	Cu(OTf)₂	AgOTf/PivOH	TFE	66	Trace
15^c	Cu(OTf)₂	AgOTf/NaOAc	TFE	Trace	ND
16^c	Cu(OTf)₂	AgOTf/Ag₂O	TFE	40	Trace
17^c,d	Cu(OTf)₂	AgOTf/CuO	TFE	74	Trace
18^c,e	Cu(OTf)₂	AgOTf/CuO	TFE	35	Trace
19^f	—	AgNTf₂/1-AdCOOH	TFE	ND	79

Entry	Oxidant	Ag/Additive	Solvent	Yield^b/%
Entry	Oxidant	Ag/Additive	Solvent	3aa	3aa'
1	AgOAc	AgSbF₆	TFE	ND	ND
2	Cu(OAc)₂•H₂O	AgSbF₆	TFE	ND	ND
3	Cu(acac)₂	AgSbF₆	TFE	Trace	ND
4	Cu(OTf)₂	AgSbF₆	TFE	37	Trace
5	Cu(OTf)₂	AgNTf₂	TFE	40	Trace
6	Cu(OTf)₂	AgBF₄	TFE	44	Trace
7	Cu(OTf)₂	CH₃SO₃Ag	TFE	38	Trace
8	Cu(OTf)₂	AgOTf	TFE	47	Trace
9^c	Cu(OTf)₂	AgOTf	TFE	72	Trace
10^c	Cu(OTf)₂	AgOTf	MeOH	ND	ND
11^c	Cu(OTf)₂	AgOTf	EtOH	ND	ND
12^c	Cu(OTf)₂	AgOTf	DCE	ND	ND
13^c	Cu(OTf)₂	AgOTf	CCl₃CH₂OH	ND	ND
14^c	Cu(OTf)₂	AgOTf/PivOH	TFE	66	Trace
15^c	Cu(OTf)₂	AgOTf/NaOAc	TFE	Trace	ND
16^c	Cu(OTf)₂	AgOTf/Ag₂O	TFE	40	Trace
17^c,d	Cu(OTf)₂	AgOTf/CuO	TFE	74	Trace
18^c,e	Cu(OTf)₂	AgOTf/CuO	TFE	35	Trace
19^f	—	AgNTf₂/1-AdCOOH	TFE	ND	79

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Ir(III)催化新型三组分串联三氟乙氧基化反应并一锅法构建复杂酰胺化合物

Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds

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