小分子光催化C-N偶联反应

doi:10.1016/S1872-2067(25)64838-8

催化学报 ›› 2026, Vol. 80: 7-19.DOI: 10.1016/S1872-2067(25)64838-8

小分子光催化C-N偶联反应

张琳星^a, 谭昌龙^b, 祁明雨^c, 唐紫蓉^a^,^c^,^*(), 徐艺军^a^,^b^,^*()

^a福州大学化学学院, 能源与环境光催化国家重点实验室, 福建福州 350116
^b电子科技大学基础与前沿研究院, 四川成都 611731
^c电子科技大学材料与能源学院, 四川成都 611731

收稿日期:2025-06-24 接受日期:2025-08-07 出版日期:2026-01-05 发布日期:2026-01-05
通讯作者: 唐紫蓉,徐艺军
基金资助:
国家自然科学基金(22572017);国家自然科学基金(22472032);国家自然科学基金(22172030);国家自然科学基金(22072023);国家自然科学基金(U1463204);电子科技大学杰出人才科研基金(A1098531023601522);国家科技创新领军人才计划(00387072);江西省“双千计划”(jxsq2023102143);中国博士后科学基金(2023M740513);中国博士后创新人才支持计划(BX20240055)

Photocatalyzed C-N coupling reactions of small molecules

Lin-Xing Zhang^a, Chang-Long Tan^b, Ming-Yu Qi^c, Zi-Rong Tang^a^,^c^,^*(), Yi-Jun Xu^a^,^b^,^*()

^aCollege of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350116, Fujian, China
^bInstitute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of China, Chengdu 611731, Sichuan, China
^cSchool of Materials and Energy, University of Electronic Science and Technology of China, Chengdu 611731, Sichuan, China

Received:2025-06-24 Accepted:2025-08-07 Online:2026-01-05 Published:2026-01-05
Contact: Zi-Rong Tang, Yi-Jun Xu
Supported by:
National Natural Science Foundation of China(22572017);National Natural Science Foundation of China(22472032);National Natural Science Foundation of China(22172030);National Natural Science Foundation of China(22072023);National Natural Science Foundation of China(U1463204);Research Fund for Outstanding Talents at University of Electronic Science and Technology of China(A1098531023601522);Program for National Science and Technology Innovation Leading Talents(00387072);Jiangxi Province “Double Thousand Plan”(jxsq2023102143);China Postdoctoral Science Foundation(2023M740513);China National Postdoctoral Program for Innovative Talents(BX20240055)

摘要/Abstract

摘要：

将地球上丰富的小分子(如CO₂和N₂)转化为尿素、甲酰胺和氨基酸等含C-N键的高附加值有机化合物, 是可持续化学领域的前沿方向. 然而, 传统热催化方法依赖高能耗条件(如Bosch-Meiser工艺需200 °C, 210 bar)和辅助化学试剂, 严重制约可持续化生产. 受自然光合作用启发, 人工光催化技术应运而生.该技术通过直接利用光子诱导的电荷载流子或间接借助活性氧物种, 在常温常压下活化C=O, N≡N等惰性化学键, 从而实现热力学不利的小分子偶联反应. 近年研究表明, CO₂/CH₃OH与无机含氮小分子(N₂, NH₃, NO₃^-)的光催化C-N偶联反应, 能够有效合成有机含氮化合物. 鉴于该领域的快速发展及其展现的巨大潜力, 对该新兴课题进行总结具有重要意义.

本文聚焦于半导体光催化剂介导的C-N偶联反应, 系统总结了利用含碳原料(CO₂和CH₃OH)与含氮小分子(N₂, NH₃和NO₃^-)通过光催化偶联合成高附加值有机含氮化合物的最新研究进展. 首先, 阐述了光驱动C-N偶联反应的基本原理和活化机制, 包括直接活化和活性氧物种介导的间接活化两种路径. 在此基础上, 进一步深入分析了尿素、甲酰胺、甘氨酸和丝氨酸目标产物选择性合成过程中的催化剂设计策略与反应机理. 特别指出, 当前光催化尿素合成可通过CO₂与N₂/NH₃/NO₃^-偶联, 或CH₃OH与N₂偶联实现, 但该过程仍面临选择性差、活性低及反应机理不明确等挑战. 而甲酰胺的合成可通过CH₃OH与NH₃脱氢偶联完成. 值得注意的是, 与C₁有机氮化合物(尿素和甲酰胺)的合成不同, 氨基酸的合成不仅需要精确调控C-N偶联过程, 还需要严格控制C-C偶联步骤, 以确保目标分子结构的精准构建. 在展望部分, 提出未来研究可通过缺陷工程、构建多活性位点协同催化体系、设计异质结构半导体及开发连续流动光反应器等策略提升反应性能; 强调拓展C源与N源种类以合成多样化含氮有机化合物; 建议结合先进的原位分析技术、理论模拟与同位素标记实验深入揭示反应机理; 同时指出, 可融入机器学习与人工智能技术, 为催化剂设计与反应优化提供新范式, 从而推动太阳能驱动C-N偶联反应的可持续发展.

综上, 本文系统归纳了半导体光催化小分子C-N偶联反应合成尿素、甲酰胺、甘氨酸和丝氨酸的研究现状, 深入剖析了当前面临的选择性调控难题、催化活性瓶颈及机理解析困境等现存挑战, 并探讨了未来发展方向, 旨在为有机含氮化合物的高效合成及其催化体系设计提供理论参考.

关键词: 光催化C-N偶联反应, 小分子, 尿素, 甲酰胺, 氨基酸

Abstract:

Catalytic coupling of abundant CO₂ or renewable CH₃OH with nitrogenous small molecules, such as N₂, NH₃, and NO₃^-, has emerged as a promising strategy for synthesizing high-value organonitrogen compounds. However, conventional thermal catalysis for C-N bond formation often relies on external chemical reagents and energy-intensive conditions, raising concerns about process sustainability. Photocatalysis offers a sustainable alternative by utilizing sunlight to generate high-energy electron-hole pairs in semiconductors, which can activate inert chemical bonds (e.g., C=O and N≡N) for programmed coupling under ambient conditions. In this review, we dissect the fundamental activation mechanisms underlying photon-mediated C‒N coupling reactions, highlight key recent breakthroughs in the synthesis of urea, formamide, and amino acids, and analyze persistent challenges alongside emerging opportunities. This work aims to deepen the understanding of photocatalytic C-N coupling reactions and inspire research interest in sustainable nitrogen fixation and carbon utilization.

Key words: Photocatalytic C-N coupling reactions, Small molecules, Urea, Formamide, Amino acids

张琳星, 谭昌龙, 祁明雨, 唐紫蓉, 徐艺军. 小分子光催化C-N偶联反应[J]. 催化学报, 2026, 80: 7-19.

Lin-Xing Zhang, Chang-Long Tan, Ming-Yu Qi, Zi-Rong Tang, Yi-Jun Xu. Photocatalyzed C-N coupling reactions of small molecules[J]. Chinese Journal of Catalysis, 2026, 80: 7-19.

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图/表 11

Fig. 1. Schematic diagram of photocatalytic synthesis of organonitrogen compounds by coupling CO2/CH3OH with nitrogenous small molecules (N2, NH3, and NO3-).

Fig. 2. The main typical reaction pathways for the photosynthesis of C-N compounds from various C and N sources: coupling of CO2 and NO3- to form urea (a), coupling of CO2 and N2 to form urea (b), coupling of CO2 and NH3 to form urea (c), coupling of CH3OH and N2 to form urea (d), coupling of CO2 and NH3 to form serine (e), coupling of CH3OH and NH3 to form formamide (f), coupling CH3OH and NO3- to form glycine (g), alternative coupling of CH3OH and NH3 to form formamide (h), and alternative coupling of CO2 and N2 to form urea (i). The asterisk represents the reaction intermediate adsorbed on the catalyst surface.

Table 1 Summary of photocatalytic urea synthesis via coupling carbonaceous with nitrogenous small molecules.

Photocatalyst	C source	N source	Urea yield	AQY ^a	Light source	Ref. Year
Ti³⁺-TiO₂/Fe-CNTs	CO₂	N₂	8.88 μmol g^-1 h^{-1 b} (volume = 50 mL)	— ^c	300 W high-pressure Hg lamp	[32] 2021
Cu₁-TiO₂	CO₂	N₂	7.20 μmol g^-1 h^-1	—	365 nm monochromatic light	[33] 2022
Zn_0.7Ni_0.3Se/g-C₃N₄	CO₂	N₂	1.12 μmol g^-1 h^-1	—	300 W Xe lamp, λ ≥ 420 nm	[34] 2022
Pd-CeO₂	CO₂	N₂	9.2 μmol g^-1 h^-1	—	300 W Xe lamp	[35] 2023
CeO₂-Vo	CO₂	N₂	6.46 μmol g^-1 h^-1	—	300 W Xe lamp	[36] 2023
CdS@BiOBr	CO₂	N₂	15 μmol g⁻¹ h⁻¹	3.93% at 475 nm	300 W Xe lamp, λ ≥ 420 nm	[37] 2023
NiCoP/ZnIn₂S_4-_x	CO₂	N₂	13.9 μmol g⁻¹ h⁻¹	—	300 W Xe lamp, λ > 420 nm	[38] 2023
Ni₁-CdS/WO₃	CO₂	N₂	10.4 μmol g⁻¹ h⁻¹	0.15% at 385 nm	Xe lamp, 200 ≤ λ ≤ 800 nm	[25] 2024
Ru₁-TiO₂	CO₂	N₂	24.95 μmol g⁻¹ h⁻¹	6.3% at 420 nm	300 W Xe lamp	[39] 2024
SiW₆Mo₆@MIL-101(Cr) ^d	CO₂	N₂	19.1 μmol g⁻¹ h⁻¹	—	300 W Xe lamp	[40] 2024
SrTiO₃-FeS-CoWO₄	CO₂	N₂	134.1 μmol g⁻¹ h⁻¹	—	300 W Xe lamp, λ ≥ 420 nm	[41] 2024
at.-Pd@TiO₂/Gr ^e	CO₂	N₂	0.54 mmol g_Pd⁻¹ h^−1f	—	300 W Xe lamp, λ ≥ 400 nm	[42] 2024
Ru-Cu/CeO₂	CO₂	N₂	16.7 μmol g⁻¹ h⁻¹	—	Xe lamp	[43] 2025
Ru₁/CeO₂-V_O	CO₂	N₂	13.73 μmol g⁻¹ h⁻¹	0.012% at 365 nm	300 W Xe lamp	[44] 2025
ZCS@Cu/Fe-MOF	CO₂	N₂	15.8 μmol g⁻¹ h⁻¹	—	300 W Xe lamp, λ > 420 nm	[45] 2025
Ni₁/TiO_2-_x	CO₂	N₂	15.73 μmol g⁻¹ h⁻¹	0.93% at 350 nm	300 W Xe lamp	[46] 2025
Pt cluster/TiO₂	CH₃OH	N₂	105.68 μmol g⁻¹ h⁻¹	—	300 W Hg lamp, 200 ≤ λ ≤ 800 nm	[47] 2024
Pd/LTA-3A	CO₂	NH₃	87.0 μmol g_Pd⁻¹ h⁻¹	—	300 W Xe lamp	[48] 2021
at.-Pd@TiO₂/Gr ^e	CO₂	NH₃	1.51 mmol g_Pd⁻¹ h⁻¹	—	300 W Xe lamp, λ ≥ 400 nm	[42] 2024
3D-TBBD-COF	CO₂	NH₃	523.0 μmol g⁻¹ h⁻¹	0.32% at 420 nm	300 W Xe lamp	[49] 2025
P25-4h	CO	NH₃	904.3 μmol g⁻¹ h⁻¹	—	300 W Xe lamp	[50] 2025
Q-TiO₂/PVPD film ^g	CO₂	NO₃^-	1.12 μmol h⁻¹	—	500 W high-pressure Hg lamp, λ ≥ 300 nm	[51] 1998
Q-TiO₂/SiO₂ film	CO₂	NO₃^-	1.07 μmol h⁻¹	—	500 W high pressure Hg lamp, λ ≥ 300 nm	[52] 1998
TiO₂/Cu-PVA-PAH/PSS ^h	CO₂	NO₃^-	0.31 mmol L⁻¹ h⁻¹	—	Hamamatsu E7536 Hg-Xe lamp, λ > 340 nm	[53] 2005
PFD:TiO₂/Cu ⁱ	CO₂	NO₃^-	1.1 mmol L⁻¹ h⁻¹	—	120 W high-pressure Hg lamp, λ ≤ 300 nm	[54] 2005
Fe₂TiO₅/HZSM-5	CO₂	NO₃^-	17.36 μmol g⁻¹ h⁻¹	—	250 W high-pressure Hg lamp	[55] 2011
at.-Pd@TiO₂/Gr ^e	CO₂	NO₃^-	1.62 mmol g_Pd⁻¹ h⁻¹	1.05% at 400 nm	300 W Xe lamp, λ ≥ 400 nm	[42] 2024
Cs₂CuBr₄/TiO_x-Ar ^j	CO₂	NO₃^-	3.66 μmol g⁻¹ h⁻¹	0.022% at 405 nm	LED light	[56] 2025

Table 1 Summary of photocatalytic urea synthesis via coupling carbonaceous with nitrogenous small molecules.

Photocatalyst	C source	N source	Urea yield	AQY ^a	Light source	Ref. Year
Ti³⁺-TiO₂/Fe-CNTs	CO₂	N₂	8.88 μmol g^-1 h^{-1 b} (volume = 50 mL)	— ^c	300 W high-pressure Hg lamp	[32] 2021
Cu₁-TiO₂	CO₂	N₂	7.20 μmol g^-1 h^-1	—	365 nm monochromatic light	[33] 2022
Zn_0.7Ni_0.3Se/g-C₃N₄	CO₂	N₂	1.12 μmol g^-1 h^-1	—	300 W Xe lamp, λ ≥ 420 nm	[34] 2022
Pd-CeO₂	CO₂	N₂	9.2 μmol g^-1 h^-1	—	300 W Xe lamp	[35] 2023
CeO₂-Vo	CO₂	N₂	6.46 μmol g^-1 h^-1	—	300 W Xe lamp	[36] 2023
CdS@BiOBr	CO₂	N₂	15 μmol g⁻¹ h⁻¹	3.93% at 475 nm	300 W Xe lamp, λ ≥ 420 nm	[37] 2023
NiCoP/ZnIn₂S_4-_x	CO₂	N₂	13.9 μmol g⁻¹ h⁻¹	—	300 W Xe lamp, λ > 420 nm	[38] 2023
Ni₁-CdS/WO₃	CO₂	N₂	10.4 μmol g⁻¹ h⁻¹	0.15% at 385 nm	Xe lamp, 200 ≤ λ ≤ 800 nm	[25] 2024
Ru₁-TiO₂	CO₂	N₂	24.95 μmol g⁻¹ h⁻¹	6.3% at 420 nm	300 W Xe lamp	[39] 2024
SiW₆Mo₆@MIL-101(Cr) ^d	CO₂	N₂	19.1 μmol g⁻¹ h⁻¹	—	300 W Xe lamp	[40] 2024
SrTiO₃-FeS-CoWO₄	CO₂	N₂	134.1 μmol g⁻¹ h⁻¹	—	300 W Xe lamp, λ ≥ 420 nm	[41] 2024
at.-Pd@TiO₂/Gr ^e	CO₂	N₂	0.54 mmol g_Pd⁻¹ h^−1f	—	300 W Xe lamp, λ ≥ 400 nm	[42] 2024
Ru-Cu/CeO₂	CO₂	N₂	16.7 μmol g⁻¹ h⁻¹	—	Xe lamp	[43] 2025
Ru₁/CeO₂-V_O	CO₂	N₂	13.73 μmol g⁻¹ h⁻¹	0.012% at 365 nm	300 W Xe lamp	[44] 2025
ZCS@Cu/Fe-MOF	CO₂	N₂	15.8 μmol g⁻¹ h⁻¹	—	300 W Xe lamp, λ > 420 nm	[45] 2025
Ni₁/TiO_2-_x	CO₂	N₂	15.73 μmol g⁻¹ h⁻¹	0.93% at 350 nm	300 W Xe lamp	[46] 2025
Pt cluster/TiO₂	CH₃OH	N₂	105.68 μmol g⁻¹ h⁻¹	—	300 W Hg lamp, 200 ≤ λ ≤ 800 nm	[47] 2024
Pd/LTA-3A	CO₂	NH₃	87.0 μmol g_Pd⁻¹ h⁻¹	—	300 W Xe lamp	[48] 2021
at.-Pd@TiO₂/Gr ^e	CO₂	NH₃	1.51 mmol g_Pd⁻¹ h⁻¹	—	300 W Xe lamp, λ ≥ 400 nm	[42] 2024
3D-TBBD-COF	CO₂	NH₃	523.0 μmol g⁻¹ h⁻¹	0.32% at 420 nm	300 W Xe lamp	[49] 2025
P25-4h	CO	NH₃	904.3 μmol g⁻¹ h⁻¹	—	300 W Xe lamp	[50] 2025
Q-TiO₂/PVPD film ^g	CO₂	NO₃^-	1.12 μmol h⁻¹	—	500 W high-pressure Hg lamp, λ ≥ 300 nm	[51] 1998
Q-TiO₂/SiO₂ film	CO₂	NO₃^-	1.07 μmol h⁻¹	—	500 W high pressure Hg lamp, λ ≥ 300 nm	[52] 1998
TiO₂/Cu-PVA-PAH/PSS ^h	CO₂	NO₃^-	0.31 mmol L⁻¹ h⁻¹	—	Hamamatsu E7536 Hg-Xe lamp, λ > 340 nm	[53] 2005
PFD:TiO₂/Cu ⁱ	CO₂	NO₃^-	1.1 mmol L⁻¹ h⁻¹	—	120 W high-pressure Hg lamp, λ ≤ 300 nm	[54] 2005
Fe₂TiO₅/HZSM-5	CO₂	NO₃^-	17.36 μmol g⁻¹ h⁻¹	—	250 W high-pressure Hg lamp	[55] 2011
at.-Pd@TiO₂/Gr ^e	CO₂	NO₃^-	1.62 mmol g_Pd⁻¹ h⁻¹	1.05% at 400 nm	300 W Xe lamp, λ ≥ 400 nm	[42] 2024
Cs₂CuBr₄/TiO_x-Ar ^j	CO₂	NO₃^-	3.66 μmol g⁻¹ h⁻¹	0.022% at 405 nm	LED light	[56] 2025

Fig. 3. (a) Schematic of oxygen vacancy formation. EPR spectra (b), N2-TPD spectra (c), CO2-TPD spectra (d), urea production rates (e) of CeO2-Purchase (commercial) and CeO2 samples heat-treated at different temperatures. (f) Mass spectrum of CeO2-500. Gibbs free energy diagrams for urea production via alternating pathway (g) and distal pathway (h). Reprinted with permission [36]. Copyright 2024, Wiley VCH.

Fig. 4. (a) EPR spectra of Ni1-CdS/WO3 treated under different atmospheres. (b) Results of comparative experiments on Ni1-CdS/WO3 under different conditions, with error bars indicating the mean absolute deviation from a minimum of three independent tests. (c) In-situ FTIR spectra monitoring intermediates in photocatalytic urea synthesis over Ni1-CdS/WO3. (d) Gibbs free energy diagrams of the urea synthesis pathway over Ni1-CdS/WO3 catalyst. (e) Schematic diagram illustrating the mechanism of photocatalytic urea synthesis over the Ni1-CdS/WO3 catalyst. Reprinted with permission [25]. Copyright 2024, Wiley-VCH.

Fig. 5. (a) Schematic diagram of the synthesis of at.-Pd@TiO2/Gr catalyst. (b) DFT calculated free-energy diagrams for the coupling of NH3 and CO2 to urea catalyzed by at.-Pd@TiO2/Gr. Insets display atomic configurations corresponding to each step. Reprinted with permission [42]. Copyright 2024, Chinese Chemical Society. (c) The speculative mechanism for urea synthesis involving the coupling of CO2 and NO3?. Reprinted with permission [55]. Copyright 2012, Wiley-VCH. (d) The FTIR spectra of CCBT-Ar under different conditions. (e) Schematic illustration of the CO2 and NO3? co-reduction over the CCBT-Ar catalyst. Reprinted with permission [56]. Copyright 2024, Elsevier.

Fig. 6. (a) Schematic diagram of the N2 activation mechanism on a Pt center. (b) EPR spectra of TiO2 and Pt cluster/TiO2 under dark and light irradiation conditions. (c) Calculated C-N bond length for the coupling of *CHO group with N-containing intermediates generated during N2 reduction. (d) Proposed reaction pathway for urea synthesis via the coupling of CH3OH with N2. Reprinted with permission [47]. Copyright 2024, Wiley-VCH.

Fig. 7. (a) EPR spectra in the NH3 and CH3OH system (under an atmosphere of 20% O2, 2 min light irradiation), with simulated signals of DMPO-NH2, DMPO-CH2OH and DMPO-OOH. (b) EPR spectra in the NH3 system (under an atmosphere of 20% O2 and Ar, 2 min light irradiation), with simulated signals of DMPO-NH2 and DMPO-OH. (c) The proposed reaction pathways for formamide synthesis. Reprinted with permission [27]. Copyright 2024, Wiley-VCH. (d) Photocatalytic H2 and formamide production performance and hole selectivity over different metal-loaded CdS. (e) Schematic of photocatalytic formamide synthesis over Pt-CdS. Reprinted with permission [78]. Copyright 2025, Wiley-VCH.

Fig. 8. (a) Glycine synthesis rates within diverse anatase TiO2 systems. (b) Glycine yield rates over Ba2+-TiO2 under different reactants. (c) In-situ EPR spectra of TiO2 and Ba2+-TiO2 in a CH3OH and NO3- mixture under light or dark conditions. (d) The proposed mechanism of glycine synthesis from the photocatalytic conversion of CH3OH and NO3-. Reprinted with permission [82]. Copyright 2024, Wiley-VCH.

Fig. 9. Photocatalytic activity for amino acids (a) and other products (b) over left- and right-handed mesostructured ZnS (denoted as L-CMZ and D-CMZ), racemic and achiral mesostructured ZnS (denoted as RMZ and AMZ). Error bars signify the standard deviation derived from the measurements of the five independent tests. (c) The pathway for synthesizing (i) serine, (ii) alanine and (iii) glycine. Reprinted with permission [85]. Copyright 2025, Elsevier.

Fig. 10. Challenges and perspective in photocatalyzed C-N coupling reactions of small molecules for organonitrogen compounds synthesis.

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小分子光催化C-N偶联反应

Photocatalyzed C-N coupling reactions of small molecules

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