Reduction of Nitro Group by Sulfide and Its Applications in Amine Synthesis

doi:10.6023/cjoc202207029

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (2): 491-502.DOI: 10.6023/cjoc202207029 Previous Articles Next Articles

硫化物还原硝基在胺类合成中的应用

时广辉^†, 杜云哲^†, 高媛媛^*(), 贾慧劼, 洪海龙, 韩利民, 竺宁^*()

内蒙古工业大学化工学院二氧化碳资源化利用自治区高等学校重点实验室内蒙古自治区CO₂捕集与资源化工程技术研究中心呼和浩特 010051

收稿日期:2022-07-23 修回日期:2022-09-19 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(21865020); 国家自然科学基金(21362019); 内蒙古自然科学基金重大项目(2021ZD02); 鄂尔多斯市科技计划(2022YY011); 内蒙古自治区“草原英才”和内蒙古自治区高等学校CO2资源化利用创新团队(NMGIRT2212)

Reduction of Nitro Group by Sulfide and Its Applications in Amine Synthesis

Guanghui Shi^†, Yunzhe Du^†, Yuanyuan Gao(), Huijie Jia, Hailong Hong, Limin Han, Ning Zhu()

Key Laboratory of CO₂ Resource Utilization at Universities of Inner Mongolia Autonomous Region, Inner Mongolia Engineering Research Center for CO₂ Capture and Utilization, Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051

Received:2022-07-23 Revised:2022-09-19 Published:2022-10-24
Contact: *E-mail: gaoyuanyuan@imut.edu.cn;zhuning@imut.edu.cn
About author:
†(The authors contributed equally to this work).
Supported by:
National Natural Science Foundation of China(21865020); National Natural Science Foundation of China(21362019); Natural Science Foundation of Inner Mongolia(2021ZD02); Ordos Science and Technology Projects(2022YY011); Program for Grassland Excellent Talents of Inner Mongolia Autonomous Region, and the Innovation Research Team of CO2 Resource Utilization in Universities of Inner Mongolia Autonomous Region(NMGIRT2212)

Aniline and its derivatives, as the basic aromatic amine compounds, are widely used in different fields such as chemistry, biology, medicine, dyes, polymer materials and agriculture. Moreover, hydrogenation reduction of nitrobenzene is a simple method for the synthesis of aniline. According to the difference of proton/electron donor, the reduction of nitrobenzene can be divided into Bechamp reduction, catalytic hydrogenation, catalytic hydrogen transfer and Zinin reduction. Zinin reduction is a method for preparing aniline by reducing nitro group by using sulfide as electron donor and protic solvent as hydrogen source, which is widely used in the laboratory research and industrial production. In this review, Zinin reduction method is systematically summarized. The principle of reduction of nitro group by sulfide is clarified from the types of sulfide reductants, the reduction mechanism of nitro group, and the application of nitro group reduction. Additionally, the reduction mechanism of nitro group by elemental sulfur, sulfide, polysulfide and hydrosulfide is detailly elucidated, and the regulatory mechanism of OH^- and H₂O in the reduction of nitro group by sulfide is explained in detail. Finally, the ability and application effect of different sulfides as reductants to reduce nitro group are analyzed in terms of atom economy.

Key words: reduction mechanism, Zinin reduction, sulfides, elemental sulfur

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Guanghui Shi, Yunzhe Du, Yuanyuan Gao, Huijie Jia, Hailong Hong, Limin Han, Ning Zhu. Reduction of Nitro Group by Sulfide and Its Applications in Amine Synthesis[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 491-502.

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Fig. & Tab. 16

Figure 1. Application of amine compounds

Figure 2. History of nitro reduction

Figure 3. Diagram of nitro reduction process

Figure 4. Common nitro compounds

Figure 5. General diagram of the nitro group reduced by sulfur-containing reagent

Figure 6. Dissociation process of sulfur and its dissociation intermediates

Scheme 1. Diagram for the mechanism of nitro reduction

Scheme 2. Investigating the reduction ability of sulfide

Scheme 3. Reduction of nitrobenzene with elemental sulfur or sodium sulfide

Figure 7. Photocatalytic reduction of nitrobenzene to aniline

Scheme 4. Reaction mechanism of nitro group reduced by elemental sulfur

Scheme 5. Reaction mechanism of nitro group reduced by sodium sulfide

Scheme 6. Reaction mechanism of nitro group reduced by sodium disulfide

Scheme 7. Reaction mechanism of nitro group reduced by sodium hydrosulfide

Scheme 8. Tandem reaction of sulfide substitution and nitro reduction

硫源	投料比	硫用量/equiv.	氧化产物	活化剂
S₈	3.0/8.0	3	${{\text{S}}_{2}}\text{O}_{3}^{2-}$	Base
S^2-	1.5	1.5	${{\text{S}}_{2}}\text{O}_{3}^{2-}$	-
$S_{2}^{2-}$	1.0	2	${{\text{S}}_{2}}\text{O}_{3}^{2-}$	Base
HS^-	3.0	3	S₈	-

Table 1. Compared the nitro reduction capacity of different sulfur sources

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硫化物还原硝基在胺类合成中的应用

Reduction of Nitro Group by Sulfide and Its Applications in Amine Synthesis

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