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

doi:10.6023/cjoc202306010

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 137-147.DOI: 10.6023/cjoc202306010 Previous Articles Next Articles

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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

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)

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

Cite this article

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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Fig. & Tab. 22

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

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

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 20. Transamination reaction based on GO[67]

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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