Copper-Promoted Trifluoromethylthiolation of Anilines with CF3SO2Na

doi:10.6023/cjoc202203031

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (2): 679-685.DOI: 10.6023/cjoc202203031 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

铜促进的苯胺类化合物与CF₃SO₂Na的三氟甲硫基化反应

Yasir Mumtaz^a,†, 刘杰^a^,^*,†(), 黄鑫^b

a 南京理工大学化学与化工学院南京 210094
b 浙江师范大学先进催化材料教育部重点实验室浙江金华 321004

收稿日期:2022-07-03 修回日期:2022-08-30 发布日期:2022-10-24
作者简介:
†共同第一作者
基金资助:
国家自然科学基金(21776138); 国家自然科学基金(22078161); 国家自然科学基金(22108124); 国家自然科学基金(21901232); 中央高校基本科研业务费专项资金(30918011314); 中央高校基本科研业务费专项资金(30922010403); 江苏省自然科学基金(BK20141394); 江苏省青蓝计划和六大高峰人才资助项目

Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na

Yasir Mumtaz^a,†, Jie Liu^a,†(), Xin Huang^b

a School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094
b Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Normal University, Jinhua, Zhejiang 321004

Received:2022-07-03 Revised:2022-08-30 Published:2022-10-24
Contact: *E-mail: Liu-J@njust.edu.cn
About author:
†(These authors contributed equally to this work).
Supported by:
National Natural Science Foundation of China(21776138); National Natural Science Foundation of China(22078161); National Natural Science Foundation of China(22108124); National Natural Science Foundation of China(21901232); Fundamental Research Funds for the Central Universities(30918011314); Fundamental Research Funds for the Central Universities(30922010403); Natural Science Foundation of Jiangsu Province(BK20141394); Qing Lan and Six Talent Peaks in Jiangsu Province

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Abstract

An inexpensive and easily accessible sodium trifluoromethyl sulfinate (CF₃SO₂Na) was employed as the trifluoromethylthio source, while anilines were used as the starting materials in a process for the synthesis of copper-promoted aryl(trifluoromethyl)sulfanes. Trifluoromethylthiolation of aromatic rings in one pot over two steps is made possible by the presence of a phosphine reducing agent. In the reaction, the copper salt promotes the conversion of trifluoromethylthio anion, and the reaction offers an effective and practical way to create derivatives of trifluoromethylthio substituted benzene.

Key words: aniline, sodium trifluoromethanesulfinate, phosphine reducing agent, trifluoromethylthiolation

Cite this article

Yasir Mumtaz, Jie Liu, Xin Huang. Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 679-685.

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Fig. & Tab. 7

References 30

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Entry	[P]	Cu salt	Solvent	Temp./℃	Yield/%^b
1	PPh₃	CuI	MeCN	50	23
2	PMe₃	CuI	MeCN	50	10
3	PPh₂Me	CuI	MeCN	50	0
4	PCy₃	CuI	MeCN	50	0
5	PPh₂Cl	CuI	MeCN	50	38
6	PPh₂Cl	CuBr	MeCN	50	30
7	PPh₂Cl	Cu(MeCN)₄PF₆	MeCN	50	35
8	PPh₂Cl	CuSCN	MeCN	50	30
9	PPh₂Cl	CuCl₂	MeCN	50	45
10	PPh₂Cl	CuSO₄	MeCN	50	60
11	PPh₂Cl	CuSO₄	DCM	50	32
12	PPh₂Cl	CuSO₄	THF	50	20
13	PPh₂Cl	CuSO₄	DCE	50	36
14	PPh₂Cl	CuSO₄	DMSO	50	15
15	PPh₂Cl	CuSO₄	MeCN	25	5
16	PPh₂Cl	CuSO₄	MeCN	60	68
17	PPh₂Cl	CuSO₄	MeCN	70	80 (75^c)
18	PPh₂Cl	CuSO₄	MeCN	80	78
19	PPh₂Cl	CuSO₄(10 mol%)	MeCN	70	43
20	PPh₂Cl	CuSO₄(5 mol%)	MeCN	70	16
21	PPh₂Cl	-	MeCN	70	0
22	PPh₂Cl	CuSO₄	MeCN	70	43% ^d

Entry	[P]	Cu salt	Solvent	Temp./℃	Yield/%^b
1	PPh₃	CuI	MeCN	50	23
2	PMe₃	CuI	MeCN	50	10
3	PPh₂Me	CuI	MeCN	50	0
4	PCy₃	CuI	MeCN	50	0
5	PPh₂Cl	CuI	MeCN	50	38
6	PPh₂Cl	CuBr	MeCN	50	30
7	PPh₂Cl	Cu(MeCN)₄PF₆	MeCN	50	35
8	PPh₂Cl	CuSCN	MeCN	50	30
9	PPh₂Cl	CuCl₂	MeCN	50	45
10	PPh₂Cl	CuSO₄	MeCN	50	60
11	PPh₂Cl	CuSO₄	DCM	50	32
12	PPh₂Cl	CuSO₄	THF	50	20
13	PPh₂Cl	CuSO₄	DCE	50	36
14	PPh₂Cl	CuSO₄	DMSO	50	15
15	PPh₂Cl	CuSO₄	MeCN	25	5
16	PPh₂Cl	CuSO₄	MeCN	60	68
17	PPh₂Cl	CuSO₄	MeCN	70	80 (75^c)
18	PPh₂Cl	CuSO₄	MeCN	80	78
19	PPh₂Cl	CuSO₄(10 mol%)	MeCN	70	43
20	PPh₂Cl	CuSO₄(5 mol%)	MeCN	70	16
21	PPh₂Cl	-	MeCN	70	0
22	PPh₂Cl	CuSO₄	MeCN	70	43% ^d

铜促进的苯胺类化合物与CF₃SO₂Na的三氟甲硫基化反应

Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na

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铜促进的苯胺类化合物与CF3SO2Na的三氟甲硫基化反应