铜催化亚磺酸钠盐参与的萘胺远程磺酰化反应

doi:10.6023/cjoc202106030

有机化学 ›› 2021, Vol. 41 ›› Issue (11): 4370-4377.DOI: 10.6023/cjoc202106030 上一篇下一篇

研究论文

铜催化亚磺酸钠盐参与的萘胺远程磺酰化反应

周翔, 余茹鉴, 王金涛, 廖向文, 熊艳师^*()

江西科技师范大学药学院江西省药物分子设计与评价重点实验室南昌 330013

收稿日期:2021-06-15 修回日期:2021-07-21 发布日期:2021-08-17
通讯作者: 熊艳师
作者简介:
† 共同第一作者.
基金资助:
江西省教育厅青年项目(GJJ190619); 江西省教育厅青年项目(GJJ201143); 江西科技师范大学博士科研启动基金(2019BSQD016)

Copper-Catalyzed Remote Sulfonylation of 1-Naphthylamides with Sodium-Sulfinates

Xiang Zhou, Rujian Yu, Jiantao Wang, Xiangwen Liao, Yanshi Xiong()

Jiangxi Provincial Key Laboratory of Drug Design and Evaluation, School of Pharmacy, Jiangxi Science & Technology Normal University, Nanchang 330013

Received:2021-06-15 Revised:2021-07-21 Published:2021-08-17
Contact: Yanshi Xiong
About author:
† These authors contributed equally to this work.
Supported by:
Department Education Science and Technology Research Project of Jiangxi Province(GJJ190619); Department Education Science and Technology Research Project of Jiangxi Province(GJJ201143); PhD Research Startup Foundation of Jiangxi Science & Technology Normal University(2019BSQD016)

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摘要/Abstract

报道了一种简单且温和的铜催化萘-1-胺与亚磺酸钠和亚磺酸锂的磺酰化反应. 在反应以碘作为氧化剂, 在比较温和的反应条件下, 可以高选择性地实现萘环C(4)的磺酰化反应, 并且以中等至较高产率生成了各种砜类衍生物.

关键词: 铜催化, 磺酰化, 远程C—H官能团化

A simple and mild copper-catalyzed sulfonylation of naphthalen-1-amine with sodium and lithium sulfinates is reported. In the presence of iodine as oxidant a highly site-selective C—H functionalization at the C(4) position took place. The reaction proceeded readily mild conditions and various sulfones were synthesized in moderate to high yields.

Key words: copper-catalyzed, sulfonylation, remote C—H functionalization

引用此文

周翔, 余茹鉴, 王金涛, 廖向文, 熊艳师. 铜催化亚磺酸钠盐参与的萘胺远程磺酰化反应[J]. 有机化学, 2021, 41(11): 4370-4377.

Xiang Zhou, Rujian Yu, Jiantao Wang, Xiangwen Liao, Yanshi Xiong. Copper-Catalyzed Remote Sulfonylation of 1-Naphthylamides with Sodium-Sulfinates[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4370-4377.

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Entry	Catalyst	Oxidant (equiv.)	Solvent	Yield^b/%
1	CuBr₂	—	DCE	20
2	CuBr₂	I₂ (2.0)	DCE	55
3	CuBr₂	TBHP (2.0)	DCE	32
4	CuBr₂	DTBP (2.0)	DCE	27
5	CuBr₂	PhI(OAc)₂ (2.0)	DCE	40
6	CuBr₂	BQ (2.0)	DCE	17
7	CuBr₂	Ag₂CO₃ (2.0)	DCE	15
8	CuBr₂	I₂ (1.0)	DCE	37
9	CuBr₂	I₂ (3.0)	DCE	90
10	Cu(OAc)₂	I₂ (3.0)	DCE	35
11	CuCl₂	I₂ (3.0)	DCE	47
12	Cu(OTf)₂	I₂ (3.0)	DCE	27
13	Cu(OAc)₂•H₂O	I₂ (3.0)	DCE	35
14	CuO	I₂ (3.0)	DCE	Trace
15	—	I₂ (3.0)	DCE	Trace
16	CuBr₂	I₂ (3.0)	CH₃CN	57
17	CuBr₂	I₂ (3.0)	THF	33
18	CuBr₂	I₂ (3.0)	DMSO	67
19	CuBr₂	I₂ (3.0)	DMF	45
20	CuBr₂	I₂ (3.0)	Toluene	57
21	CuBr₂	I₂ (3.0)	MeOH	23
22^d	CuBr₂	I₂ (3.0)	DCE	66
23^e	CuBr₂	I₂ (3.0)	DCE	75

Entry	Catalyst	Oxidant (equiv.)	Solvent	Yield^b/%
1	CuBr₂	—	DCE	20
2	CuBr₂	I₂ (2.0)	DCE	55
3	CuBr₂	TBHP (2.0)	DCE	32
4	CuBr₂	DTBP (2.0)	DCE	27
5	CuBr₂	PhI(OAc)₂ (2.0)	DCE	40
6	CuBr₂	BQ (2.0)	DCE	17
7	CuBr₂	Ag₂CO₃ (2.0)	DCE	15
8	CuBr₂	I₂ (1.0)	DCE	37
9	CuBr₂	I₂ (3.0)	DCE	90
10	Cu(OAc)₂	I₂ (3.0)	DCE	35
11	CuCl₂	I₂ (3.0)	DCE	47
12	Cu(OTf)₂	I₂ (3.0)	DCE	27
13	Cu(OAc)₂•H₂O	I₂ (3.0)	DCE	35
14	CuO	I₂ (3.0)	DCE	Trace
15	—	I₂ (3.0)	DCE	Trace
16	CuBr₂	I₂ (3.0)	CH₃CN	57
17	CuBr₂	I₂ (3.0)	THF	33
18	CuBr₂	I₂ (3.0)	DMSO	67
19	CuBr₂	I₂ (3.0)	DMF	45
20	CuBr₂	I₂ (3.0)	Toluene	57
21	CuBr₂	I₂ (3.0)	MeOH	23
22^d	CuBr₂	I₂ (3.0)	DCE	66
23^e	CuBr₂	I₂ (3.0)	DCE	75

铜催化亚磺酸钠盐参与的萘胺远程磺酰化反应

Copper-Catalyzed Remote Sulfonylation of 1-Naphthylamides with Sodium-Sulfinates

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