Photocatalyzed C-N coupling reactions of small molecules

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

Abstract

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

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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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(25)64838-8

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Figures/Tables 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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