Copper-Catalyzedortho-Sulfonylation with 5-Chloro-8-aminoquinoline Group-Directed

doi:10.6023/cjoc202005021

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 384-393.DOI: 10.6023/cjoc202005021 Previous Articles Next Articles

Special Issue: 热点论文虚拟合集

Article

铜催化的5-氯-8-氨基喹啉导向的邻位磺酰化

王向阳^a, 高君青^a, 徐学涛^a^,^*(), 方萍^b^,^*(), 梅天胜^b

a 五邑大学生物科技与大健康学院广东江门 529020
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室分子合成卓越中心上海 200032

收稿日期:2020-05-09 修回日期:2020-07-28 发布日期:2020-08-06
通讯作者: 徐学涛, 方萍
作者简介:
* Corresponding authors. E-mail: wyuchemxxt@126.com; pfang@sioc.ac.cn
共同第一作者(These authors contributed equally to this work).
基金资助:
国家自然科学基金(21772222); 国家自然科学基金(21821002); 广东省教育厅基金(2017KSYS010); 广东省教育厅基金(2017KZDXM084); 广东省教育厅基金(2019KZDZX2003); 广东省教育厅基金(2019KZDXM035)

Copper-Catalyzedortho-Sulfonylation with 5-Chloro-8-aminoquinoline Group-Directed

Xiangyang Wang^a, Junqing Gao^a, Xuetao Xu^a^,^*(), Ping Fang^b^,^*(), Tiansheng Mei^b

a School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020
b Center for Excellence in Molecular Synthesis, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2020-05-09 Revised:2020-07-28 Published:2020-08-06
Contact: Xuetao Xu, Ping Fang
Supported by:
the National Natural Science Foundation of China(21772222); the National Natural Science Foundation of China(21821002); the Department of Education of Guangdong Province(2017KSYS010); the Department of Education of Guangdong Province(2017KZDXM084); the Department of Education of Guangdong Province(2019KZDZX2003); the Department of Education of Guangdong Province(2019KZDXM035)

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Abstract

Sulfone is a common structure in natural products and active molecules, and also an important intermediate in organic synthesis. Sulfonylation is one of the most basic and important reactions in organic synthesis. The direct sulfonylation of C(sp ²)—H bond has been successfully realized by copper catalysis using 5-chloro-8-aminoquinoline (AQ') as a bidentate guiding group and various substituted sodium arylsulfites as sulfonylation reagent. This reaction has high functional group tolerance and a wide scope of substrates, including substrates with double substituents or fused rings. AQ' bidentate guiding group can be removed easily, which provides a new method for the synthesis of sulfone compounds. The reaction could be scaled up to the gram scale with a good yield.

Key words: copper catalysis, carbon hydrogen functionalization, sulfonylation

Cite this article

Xiangyang Wang, Junqing Gao, Xuetao Xu, Ping Fang, Tiansheng Mei. Copper-Catalyzedortho-Sulfonylation with 5-Chloro-8-aminoquinoline Group-Directed[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 384-393.

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Entry	[M]	Additive	Base	Solvent	Yield ^b /%
1 ^c	CuCl	PhCOOH	KOPiv	DMF	38
2 ^c	Cu(OAc) ₂ •H ₂O	PhCOOH	KOPiv	DMF	46
3 ^c	CuBr ₂	PhCOOH	KOPiv	DMF	10
4 ^c	Cu(OTf) ₂	PhCOOH	KOPiv	DMF	46
5 ^c	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	59
6 ^c	—	PhCOOH	KOPiv	DMF	Trace
7 ^cd	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	45
8 ^e	Cu(OAc) ₂	3,4-Dimethylbenzoic acid	KOPiv	DMF	66
9 ^e	Cu(OAc) ₂	2,4,6-Trimethylbenzoic acid	KOPiv	DMF	57
10 ^e	Cu(OAc) ₂	4- tert-Butylbenzoic acid	KOPiv	DMF	58
11 ^e	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	72
12 ^f	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	62
13	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	71
14	Cu(OAc) ₂	PhCOOH	—	DMF	13
15	Cu(OAc) ₂	PhCOOH	KOAc	DMF	60
16	Cu(OAc) ₂	PhCOOH	NaOPiv •H ₂O	DMF	61
17	Cu(OAc) ₂	PhCOOH	K ₂CO ₃	DMF	36
18	Cu(OAc) ₂	PhCOOH	KOPiv	DMSO	66
19	Cu(OAc) ₂	PhCOOH	KOPiv	DCE	17
20	Cu(OAc) ₂	PhCOOH	KOPiv	CH ₃CN	46
21	Cu(OAc) ₂	PhCOOH	KOPiv	1,4-Dioxane	17
22	Cu(OAc) ₂ (10 mol%)	PhCOOH (20 mol%)	KOPiv	DMF	58
23	Cu(OAc) ₂ (20 mol%)	PhCOOH (30 mol%)	KOPiv	DMF	81 (79) ^g
24	Cu(OAc) ₂ (20 mol%)	PhCOOH (40 mol%)	KOPiv	DMF	73

Entry	[M]	Additive	Base	Solvent	Yield ^b /%
1 ^c	CuCl	PhCOOH	KOPiv	DMF	38
2 ^c	Cu(OAc) ₂ •H ₂O	PhCOOH	KOPiv	DMF	46
3 ^c	CuBr ₂	PhCOOH	KOPiv	DMF	10
4 ^c	Cu(OTf) ₂	PhCOOH	KOPiv	DMF	46
5 ^c	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	59
6 ^c	—	PhCOOH	KOPiv	DMF	Trace
7 ^cd	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	45
8 ^e	Cu(OAc) ₂	3,4-Dimethylbenzoic acid	KOPiv	DMF	66
9 ^e	Cu(OAc) ₂	2,4,6-Trimethylbenzoic acid	KOPiv	DMF	57
10 ^e	Cu(OAc) ₂	4- tert-Butylbenzoic acid	KOPiv	DMF	58
11 ^e	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	72
12 ^f	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	62
13	Cu(OAc) ₂	PhCOOH	KOPiv	DMF	71
14	Cu(OAc) ₂	PhCOOH	—	DMF	13
15	Cu(OAc) ₂	PhCOOH	KOAc	DMF	60
16	Cu(OAc) ₂	PhCOOH	NaOPiv •H ₂O	DMF	61
17	Cu(OAc) ₂	PhCOOH	K ₂CO ₃	DMF	36
18	Cu(OAc) ₂	PhCOOH	KOPiv	DMSO	66
19	Cu(OAc) ₂	PhCOOH	KOPiv	DCE	17
20	Cu(OAc) ₂	PhCOOH	KOPiv	CH ₃CN	46
21	Cu(OAc) ₂	PhCOOH	KOPiv	1,4-Dioxane	17
22	Cu(OAc) ₂ (10 mol%)	PhCOOH (20 mol%)	KOPiv	DMF	58
23	Cu(OAc) ₂ (20 mol%)	PhCOOH (30 mol%)	KOPiv	DMF	81 (79) ^g
24	Cu(OAc) ₂ (20 mol%)	PhCOOH (40 mol%)	KOPiv	DMF	73

铜催化的5-氯-8-氨基喹啉导向的邻位磺酰化

Copper-Catalyzedortho-Sulfonylation with 5-Chloro-8-aminoquinoline Group-Directed

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