Fe-Catalyzed Synthesis of Sulfide-Based Aromatic Primary Amines in Water Promoted by Sodium-Ascorbate

doi:10.6023/cjoc202302008

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (8): 2800-2807.DOI: 10.6023/cjoc202302008 Previous Articles Next Articles

水相中抗坏血酸钠促进铁催化合成含硫芳香伯胺化合物

陈乡萍^a, 孟晨湘^b, 李梦娜^b, 楚尚敏^b, 朱欣欣^b, 许凯^b^,^*(), 刘澜涛^b^,^c^,^*(), 王涛^b, 张凤华^a, 李飞^a^,^*()

a 辽宁石油化工大学石油化工学院辽宁抚顺 113001
b 商丘师范学院化学化工学院药物绿色合成河南省工程实验室河南商丘 476000
c 郑州大学化学学院郑州 450001

收稿日期:2023-02-09 修回日期:2023-04-09 发布日期:2023-04-26
基金资助:
国家自然科学基金(21572126); 国家自然科学基金(21202095); 河南省科技创新团队建设计划(C20150030); 河南省高校科技创新人才支持计划(184100510011); 河南省自然科学基金(212300410379); 河南省科技攻关项目(192102110222); 河南省高等学校青年骨干教师培养计划(2021GGJS136); 河南省商丘市人才支持计划领军人才(SQRC202212004)

Fe-Catalyzed Synthesis of Sulfide-Based Aromatic Primary Amines in Water Promoted by Sodium-Ascorbate

Xiangping Chen^a, Chenxiang Meng^b, Mengna Li^b, Shangmin Chu^b, Xinxin Zhu^b, Kai Xu^b(), Lantao Liu^b^,^c(), Tao Wang^b, Fenghua Zhang^a, Fei Li^a()

a College of Petrochemical Engineering, Liaoning Petrochemical University, Fushun, Liaoning 113001
b Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000
c College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2023-02-09 Revised:2023-04-09 Published:2023-04-26
Contact: *E-mail: liult05@iccas.ac.cn; xuk1008@163.com; lnpulf@126.com
Supported by:
The National Natural Science Foundation of China(21572126); The National Natural Science Foundation of China(21202095); The Technicians Troop Construction Projects of Henan Province(C20150030); The Program of Science and Technology Innovation Talents of Henan Province(184100510011); The Natural Science Foundation of Henan Province(212300410379); The Key Scientific, Technological Project of Henan Province(192102110222); The Young Core Instructor Project from the Higher Education Institutions of Henan Province(2021GGJS136); The Leading Talent Funding Project of Shangqiu Talent Support Plan in Henan Province(SQRC202212004)

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Abstract

A practical method for Fe-catalyzed and sodium-ascorbate-promoted synthesis of sulfide-based aromatic primary amines in water from nitroaryl fluorides and thiols has been established. This protocol enables the construction of C—S bonds and the reduction of nitro groups in situ. The remarkable features of this one-pot two-step reaction in water include the direct usage of both a less toxic iron catalyst and naturally occurring sodium-ascorbate as the additive, mostly decent to excellent yields, good functional group tolerance as well as the ability to be scaled up.

Key words: aqueous phase reaction, reduction reaction, iron, catalysis, aromatic primary amine

Cite this article

Xiangping Chen, Chenxiang Meng, Mengna Li, Shangmin Chu, Xinxin Zhu, Kai Xu, Lantao Liu, Tao Wang, Fenghua Zhang, Fei Li. Fe-Catalyzed Synthesis of Sulfide-Based Aromatic Primary Amines in Water Promoted by Sodium-Ascorbate[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2800-2807.

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Fig. & Tab. 4

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水相中抗坏血酸钠促进铁催化合成含硫芳香伯胺化合物

Fe-Catalyzed Synthesis of Sulfide-Based Aromatic Primary Amines in Water Promoted by Sodium-Ascorbate

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Entry	Deviation from the model conditions	Yield ^b/%
1	None	88
2	Fe(acac)₃ (5 mol%), 2,2'-bpy (5 mol%)	83
3	No Fe(acac)₃, no 2,2'-bpy	17
4	FeCl₂ instead of Fe(acac)₃	75
5	FeCl₃ instead of Fe(acac)₃	45
6	Fe(OAc)₂ instead of Fe(acac)₃	72
7	1,10-Phenanthroline instead of 2,2'-bpy	76
8	Cs₂CO₃ instead of K₂CO₃	70
9	K₃PO₄ instead of K₂CO₃	53
10	KOAc instead of K₂CO₃	44
11	No Na-ascorbate	20
12	Na-erythorbate instead of Na-ascorbate	74
13	AscH₂ instead of Na-ascorbate	48
14	TBAI instead of TBAB	86
15	TBAC instead of TBAB	71
16	DMF, DMSO, toluene, 1,4-dioxane, CH₃CN, DCE, CH₃CH₂OH instead of H₂O	62/61/27/ 28/11/<5/8
17	Air atmosphere	69
18	Room temperature	<5

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