硫化物还原硝基在胺类合成中的应用

doi:10.6023/cjoc202207029

有机化学 ›› 2023, Vol. 43 ›› Issue (2): 491-502.DOI: 10.6023/cjoc202207029 上一篇下一篇

综述与进展

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)

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摘要/Abstract

苯胺及其衍生物作为最基础的芳香胺类化合物, 广泛应用于化学、生物、医学、染料、高分子材料和农业等不同领域, 其最简单的合成方法是通过硝基苯加氢还原. 根据质子供体和电子供体的差异可将硝基苯的还原方法分为Bechamp还原、催化氢化、催化氢转移和Zinin还原. Zinin还原是一种以硫化物为电子供体, 质子性溶剂为氢源还原硝基制备苯胺的方法, 广泛应用于实验室研究及工业生产. 系统总结了Zinin还原方法, 介绍了硫化物类还原剂, 硫化物还原硝基的反应机理和硫化物还原硝基的应用, 重点阐明了单质硫、硫化物、多硫化物与硫氢化物还原硝基的原理, 并详细分析了OH^-和H₂O在硫化物还原硝基过程中的调控机制, 最后在原子经济性方面对比分析了不同硫化物作为还原剂还原硝基的能力及应用效果.

关键词: 还原机理, Zinin还原, 硫化物, 硫磺

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

引用此文

时广辉, 杜云哲, 高媛媛, 贾慧劼, 洪海龙, 韩利民, 竺宁. 硫化物还原硝基在胺类合成中的应用[J]. 有机化学, 2023, 43(2): 491-502.

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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图/表 16

图1. 胺类化合物的应用

Figure 1. Application of amine compounds

图2. 硝基还原的历史

Figure 2. History of nitro reduction

图3. 硝基还原过程示意图

Figure 3. Diagram of nitro reduction process

图4. 常见的硝基类化合物

Figure 4. Common nitro compounds

图5. 含硫试剂还原硝基的概括图

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

图6. 硫的解离过程及其解离中间体

Figure 6. Dissociation process of sulfur and its dissociation intermediates

图式1. 硝基还原总机理图

Scheme 1. Diagram for the mechanism of nitro reduction

图式2. 硫化物还原能力的考察

Scheme 2. Investigating the reduction ability of sulfide

图式3. 硫化物还原能力的考察

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

图7. 光催化硝基苯还原成苯胺的历程

Figure 7. Photocatalytic reduction of nitrobenzene to aniline

图式4. 单质硫还原硝基的反应机理图

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

图式5. 硫化钠还原硝基的反应机理图

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

图式6. 二硫化钠还原硝基的反应机理图

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

图式7. 硫氢化钠还原硝基的反应机理图

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

图式8. 硫化物取代与硝基还原的多步串联反应

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	-

表1. 不同硫源还原硝基性能的对比a

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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