碳基非金属催化剂在有机合成领域的应用及机理研究

doi:10.6023/cjoc202306010

有机化学 ›› 2024, Vol. 44 ›› Issue (1): 137-147.DOI: 10.6023/cjoc202306010 上一篇下一篇

综述与进展

碳基非金属催化剂在有机合成领域的应用及机理研究

赵茜帆^a^,^b^,^*(), 陈永正^a^,^b, 张世明^a^,^b

a 遵义医科大学药学院贵州省绿色制药工程研究中心贵州省仿制药工程研究中心贵州省生物催化与手性药物合成重点实验室贵州遵义 563000
b 遵义医科大学基础药理教育部重点实验室特色民族药教育部国际合作联合实验室贵州遵义 563000

收稿日期:2023-06-12 修回日期:2023-08-14 发布日期:2023-08-30
基金资助:
国家自然科学基金(21865040); 国家自然科学基金(22005356); 贵州省科学技术厅(QKHPTRC[2019]1463); 遵义市科技厅(ZSKRPT-2020-5); 遵义市科技厅(ZSKH-2018-3); 遵义市科技厅(ZSKRPT-2021-5); 遵义医科大学研究生科研基金(ZYK82)

Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis

Qianfan Zhao^a^,^b(), Yongzheng Chen^a^,^b, Shiming Zhang^a^,^b

a Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000
b Key Laboratory of Basic Pharmacology of Ministry of Education, and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou 563000

Received:2023-06-12 Revised:2023-08-14 Published:2023-08-30
Contact: *E-mail: zhaoqfya@163.com
Supported by:
National Natural Science Foundation of China(21865040); National Natural Science Foundation of China(22005356); Guizhou Provincial Science and Technology Program(QKHPTRC[2019]1463); Science and Technology Department of Zunyi(ZSKRPT-2020-5); Science and Technology Department of Zunyi(ZSKH-2018-3); Science and Technology Department of Zunyi(ZSKRPT-2021-5); Graduate Research Foundation of Zunyi Medical University(ZYK82)

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摘要/Abstract

碳基非金属催化剂是指包括碳纳米管(CNTs)、氧化石墨烯(GO)、石墨烯(G)、活性炭(AC)及其掺杂或修饰后得到的材料作为用于涉及能量转换等关键反应过程的催化剂. 碳基非金属催化剂由于具有来源丰富、成本低、对环境友好、后处理简单、可持续发展等优点, 近年来被成功应用于有机合成领域. 基于碳基非金属催化剂应用于氧化反应、还原反应、取代反应和偶联反应被成功报道, 但针对碳基非金属催化剂应用于有机合成领域进行催化的活性位点的研究目前仍处于早期发展阶段. 近年来, 科学家们针对其机理的研究主要集中于对催化剂的表征分析和第一性原理计算, 但未得出相对一致的实验结论. 对碳基非金属催化剂在有机合成领域的应用及机理研究进行了综述.

关键词: 碳基非金属催化剂, 有机合成, 机理研究

Carbon nanotubes (CNTs), graphite oxide (GO), graphene (G), activated carbon (AC), and materials generated by AC after doping or modification are examples of carbon-based metal-free catalysts. These catalysts are used in critical chemical processes like energy conversion. Due to its advantages of abundant materials, low cost, environmental friendliness, straightforward post-processing and sustainable development, carbon-based metal-free catalysts have been successfully used in the field of organic synthesis in recent years. The application of carbon-based metal-free catalysts in oxidation, reduction, substitution and coupling reactions has been successfully reported. However, the research on the active site of carbon-based metal-free catalysts used in organic synthesis is still in its early stage of development. Recent research has mostly concentrated on the characterization and study of catalysts as well as first-principles predictions for their mechanisms, but generally consistent experimental conclusions have not been reached. Therefore, the application and mechanism research of carbon-based metal-free catalysts in the field of organic synthesis are reviewed.

Key words: carbon-based metal-free catalyst, organic synthesis, mechanism research

引用此文

赵茜帆, 陈永正, 张世明. 碳基非金属催化剂在有机合成领域的应用及机理研究[J]. 有机化学, 2024, 44(1): 137-147.

Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.

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图/表 22

图式1. 基于P-oCNTs催化的丁烷的氧化脱氢[24]

Scheme 1. Oxidative dehydrogenation of butane based on P-oCNTs[24]

图式2. P-oCNTs催化丁烷氧化脱氢机理示意图[24]

Scheme 2. Mechanism of oxidative dehydrogenation of butane catalyzed by P-oCNTs[24]

图式3. 丙烷在端氧扶手椅式结构的BN边缘脱氢的自由基历程

Scheme 3. Proposed radical rebound mechanism for hydrogen atom abstraction from propane to the O-terminated armchair BN edge site Hermans’s model suggests that this O-terminated edge site (one-dimensional, 1D) may lead to the observed favorable olefin selectivity[39]. This is drastically different from a 0D site[40], or a 2D site.

图式4. 基于氮掺杂石墨烯(NG)催化的醇的选择性氧化[38]

Scheme 4. Selective oxidation of alcohol based on N-doped Graphene (NG)[38]

图式5. 基于CCG催化的苯的氧化[33]

Scheme 5. Oxidation of benzene based on CCG[33]

图式6. 苯在CCG上的氧化机理[33]

Scheme 6. Proposed mechanism of the oxidation of benzene on CCG[33]

图式7. 基于碳基非金属催化剂催化的芳香族烷烃的选择性氧化[44-45]

Scheme 7. Selective oxidation of aromatic alkanes based on carbon-based metal-free catalysts[44-45]

图式8. 基于PINs催化的芳香族硫化物的氧化[46]

Scheme 8. Oxidation of aromatic sulfide based on PINs[46]

图式9. 基于GO催化的氮杂环化合物的氧化脱氢[36]

Scheme 9. Oxidative dehydrogenation of nitrogen heterocyclic compounds based on GO[36]

图1. 基于GO催化的氮杂环化合物的氧化脱氢反应的小分子实验[36]

Figure 1. Small molecular experiment of oxidative dehydrogenation of nitrogen heterocyclic compounds based on GO[36]

图式10. 基于GO催化的氮杂环化合物的氧化脱氢可能的催化机理[36]

Scheme 10. Possible catalytic mechanism of oxidative dehydrogenation of nitrogen heterocyclic compounds based on GO[36]

图式11. 基于rGO催化的氮杂环化合物的氧化脱氢[26]

Scheme 11. Oxidative dehydrogenation of nitrogen heterocyclic compounds based on rGO[26]

图式12. 基于rGO催化的氮杂环化合物的氧化脱氢可能的催化机理[26]

Scheme 12. Possible catalytic mechanism of oxidative dehydrogenation of nitrogen heterocyclic compounds based on rGO[26]

图式13. 基于生物质碳基非金属催化剂催化的氮杂环化合物的氧化脱氢[10,51]

Scheme 13. Oxidative dehydrogenation of nitrogen heterocyclic compounds based on biomass carbon-based metal-free catalysts[10,51]

图式14. 基于NCNTs催化的环己烷的氧化[52-53]

Scheme 14. Oxidation of cyclohexane based on NCNTs[52-53]

图式15. 基于碳基非金属催化剂催化的硝基苯的还原[54?-56]

Scheme 15. Reduction of nitrobenzene based on carbon-based metal-free catalysts[54?-56]

图式16. 基于GO催化的卤代反应[59-60]

Scheme 16. Halogenation reaction based on GO[59-60]

图式17. 基于活性炭催化2-氨基酚、邻苯二胺或2-氨基苯硫醇与苯甲醛偶联[63]

Scheme 17. Coupling of 2-aminophenol, o-phenylenediamine or 2-aminophenylmercaptan with benzaldehyde based on activated carbon[63]

图式18. 基于GO实现芳烃烷基化和酮烷基化[64-65]

Scheme 18. Aromatics alkylation and ketone alkylation were realized based on GO[64-65]

图式19. 基于GO催化的芳烃的三氟甲基化[66]

Scheme 19. Trifluoromethylation of aromatic hydrocarbons based on GO[66]

图式20. 基于GO催化的转氨反应[67]

Scheme 20. Transamination reaction based on GO[67]

图式22. 基于GO催化的芳烃的氧化偶联[68-69]

Scheme 22. Oxidative Coupling of aromatic hydrocarbons based on GO[68-69]

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碳基非金属催化剂在有机合成领域的应用及机理研究

Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis

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