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DOI: 10.1039/D5GC02613J (Paper) Green Chem., 2025, Advance Article

Switchable mechanical-force-induced selective reduction of nitroarenes via piezoelectric perovskite materials

Minxia Liu† a, Huiying Chen†a, Fiona Jiani Zhangb and Mingxiang Zhu*a
aThe Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, and Shanghai Frontiers Science Center of Biomimetic Catalysis, Shanghai Normal University, Shanghai 200234, China. E-mail: mingxiangzhu@shnu.edu.cn
bMinhang Crosspoint Academy at Shanghai Wenqi Private Middle School, Shanghai 200240, China

Received 26th May 2025 , Accepted 4th August 2025

First published on 5th August 2025

Abstract

Nitroarenes, as a class of environmentally hazardous pollutants with significant ecological and health risks, present critical challenges in their efficient transformation into high-value-added compounds. While reductive amination reactions have attracted considerable attention due to their remarkable reliability and functional group tolerance, they still face substantial challenges in achieving chemoselectivity control, catalytic system economy, and mild reaction conditions. This study innovatively developed a mechanocatalytic strategy with switchable selectivity, achieving the controlled synthesis of both anilines and azoxybenzenes through the precise regulation of nitroarene-reduction pathways. Employing cost-effective, environmentally benign tet-BaTiO3 as a mechanocatalyst, we demonstrated the first mechano-driven nitroarene-reduction system, establishing a versatile platform for synthesizing these two important compound classes. Mechanistic investigations revealed that strategic modulation of the proton donor and catalyst redox potential served as the pivotal mechanism governing the reaction pathway selection. Through the systematic optimization of key parameters, including the mechanocatalyst, proton donors, and additives, we achieved target product yields ranging from moderate to excellent. Comprehensive mechanistic studies elucidated the reaction pathways and operational principles underlying this precisely controlled mechanocatalytic system.


Green foundation

1. Our approach directly mitigates environmental hazards by converting toxic nitroarenes, known as persistent carcinogenic pollutants, into high-value precursors for pharmaceuticals and agrochemicals. By replacing traditional precious metals or complex catalysts with low-cost, readily available, and non-toxic perovskite materials, and substituting polluting reductants, such as sodium borohydride, with environmentally benign alcohols as hydrogen sources, we achieved the selective reduction of aromatic nitro compounds under ambient conditions, including room temperature and atmospheric air, thereby minimizing ecological and health impacts.

2. Through this switchable mechanocatalytic reductive amination strategy, simple adjustments to the reaction conditions enabled the selective reduction of 42 substrates to either anilines or azoxybenzenes with over 99% selectivity and up to 98% yield.

3. The developed switchable mechanocatalytic selective reduction system, combined with mechanistic insights into the selectivity-determining factors, broadens the application of mechanocatalysis in organic synthesis and provides innovative avenues for precision catalysis.


Introduction

Organonitrogen compounds serve as pivotal building blocks in organic synthesis and materials science.1 Developing sustainable and cost-effective production methods for these compounds has long been a shared objective across academia and industry. The selective hydrogenation of nitro compounds is an important reaction for producing various functional products.2 This methodology bypasses the conventional protection–deprotection sequences of nitrogenous functional groups, thereby significantly enhancing the reaction versatility and step economy and representing a transformative method in organic synthesis.3 Current research primarily focuses on transition metal catalysis,4–7 photocatalysis,8–12 and electrocatalysis,13–15 and these strategies have been extensively investigated. However, these reactions often face the following challenges that hinder their practical implementation: (i) the multistep electron–proton transfer processes in nitroarene reduction generate intermediates such as hydroxylamine, azoxyarenes, and azoarenes, making the selective synthesis of a single product challenging despite precise optimization of reaction conditions, and (ii) the requirements of inert atmospheres, elevated temperatures, strong bases and sophisticated catalyst systems collectively escalate the environmental burden and costs (Fig. 1a).16,17 Mechanoredox chemistry has recently emerged as a promising alternative in organic synthesis, offering distinct advantages, including solvent-free conditions, operational simplicity, ambient atmosphere compatibility, and the use of cost-effective catalysts.18 Particularly, in carbon–heteroatom bond formation,19 cyclization reactions,20 oxidation processes,18,19 and deuteration chemistry,21 piezoelectric materials have demonstrated unique capabilities to generate charge carriers through mechanical stress, enabling redox transformations. To further explore the potential of piezoelectric materials as redox catalysts for electron-transfer processes, we selected the more challenging nitroarene reductive amination, a complex six-electron, six-proton transfer process, as a model system. This investigation was aimed at elucidating the pathway regulation mechanisms and establish selective synthesis protocols for organonitrogen products.
image file: d5gc02613j-f1.tif
Fig. 1 (a ) State-of-the-art strategies for the selective reduction of nitroarenes to high-value products. (b) Switchable mechanocatalytic reduction of nitroarenes (this work).

Achieving the selective synthesis of organonitrogen derivatives through nitroaromatic hydrogenation presents a long-standing scientific challenge due to its intricate reaction pathways. The critical determinant for selectivity control lies in preferential pathway modulation and suppression of the over-reduction phenomena.22,23 Herein, we report a novel switchable, condition-controlled divergent mechanochemical reduction system for nitroarenes that enables the highly selective synthesis of either anilines or azoxybenzenes. An air-tolerant mechanocatalytic system employing cost-effective tert-BaTiO3 as the piezoelectric catalyst was established. Under base-free conditions, this system utilizes methanol as a practical proton donor to achieve the selective synthesis of aryl amine derivatives.

Through strategic modulation of the proton donor and addition of a base, we simultaneously facilitated the dehydration between nitrosobenzene and phenylhydroxylamine intermediates and regulated the redox potential of the piezoelectric catalyst to suppress the over-reduction of azoxybenzene, thereby achieving unprecedented selectivity for aniline and azoxybenzene. The operational simplicity of this oxygen-tolerant system eliminated the conventional requirement for an inert atmosphere, significantly enhancing its practical applicability (Fig. 1b).

Results and discussion

Reaction development

To commence our study, the mechano-driven reduction of nitrobenzene (1a) was carried out using a piezoelectric catalyst. After careful screening of the reaction conditions, we obtained an excellent catalytic performance, yielding 97% of aniline (2a) using 1.3 mmol tet-BaTiO3 with MeOH at room temperature under an air atmosphere and 45 Hz ball milling for 4 h (Table 1, entry 1). Control experiments revealed that the yield of aniline 2a dropped below 70% when alternative piezoelectric catalysts (Li2TiO3, PbTiO3; Table 1, entries 1–3 and Tables S1–S2) or different proton donors (H2O, EtOH, etc.; Table 1, entries 4–6 and Table S5) were employed, confirming that the combination of tet-BaTiO3 and MeOH represented the optimal condition for the selective synthesis of aromatic amine. Notably, reducing the number of steel balls, lowering the ball-milling frequency, or shortening the milling duration caused rapid declines in the yield of aniline (Tables S3 and S4). Furthermore, the yield of aniline (2a) reached 92% when MeOH was used as the solvent, closely approaching the 97% yield observed without the base. This indicates that solvent selection predominantly governs the selective reduction of nitrobenzene in this system (Table 1, entry 5). Interestingly, changing the proton donor resulted in a significant product shift, whereby azoxybenzene 3a was observed, albeit in a modest yield (30%) (Table 1, entry 6), potentially suggesting the presence of condition-controlled divergent pathways leading to both aniline 2a and azoxybenzene 3a. This observation motivated our pursuit for a reliable, condition-regulated divergent piezoelectric reduction system for nitroarenes.
Table 1 Optimization of the reaction conditions

image file: d5gc02613j-u1.tif
Entry Piezoelectric material Proton donor Additive 2a[thin space (1/6-em)]a (%) 3a[thin space (1/6-em)]a (%)
Reaction conditions: A: 1a (0.3 mmol), piezoelectric material (1.3 mmol), and proton donor (500 μL) in a stainless-steel milling jar (20 mL) with 20 stainless-steel balls (5 mm, diameter) in air at room temperature; ball-milling conditions: 4 h at 45 Hz; B: 1a (0.3 mmol), tet-BaTiO3 (1.2 mmol), isopropanol (400 μL), and additive (0.3 mmol) in a stainless-steel milling jar (20 mL) with 20 stainless-steel balls (5 mm, diameter) in air at room temperature; ball-milling conditions: 4 h at 45 Hz.a Yield of 2a–5a determined by GC using biphenyl as an internal standard.
1 (A) tet-BaTiO3 MeOH —  97  0
2 Li2TiO3 MeOH — 26 0
3 PbTiO3 MeOH — 12 0
4 tet-BaTiO3 H2O — 67 2
5 tet-BaTiO3 MeOH NaOH 92 0
6 tet-BaTiO3 Isopropanol — 19 30
7 (B) tet-BaTiO3 Isopropanol NaOH 0 92
8 tet-BaTiO3 isopropanol LiOH 6 63
9 tet-BaTiO3 Isopropanol K2CO3 9 10
10 tet-BaTiO3 Isopropanol TEA 30 23

To selectively produce 3a, a systematic optimization was conducted. Initial studies focused on the selection and loading of the proton donor. Using 1.3 mmol tet-BaTiO3 and 0.6 mmol NaOH, isopropanol outperformed other donors (n-pentanol, n-butanol, and tert-butanol), delivering 3a with an 84% yield and 85% selectivity. Deviating from the optimal isopropanol volume (500 or 300 μL instead of 400 μL) reduced the yields within 38%–78% with a compromised selectivity. Subsequent investigations highlighted the critical role of the base quantity: reducing NaOH to 0.3 mmol boosted the yield of 3a to 95% (Table S6). Screening organic and inorganic bases (Table 1, entries 7–10) yielded inferior results (10%–63%). This phenomenon originated from the synergistic effects of NaOH and isopropanol's pKa in promoting the dehydration step during nitrobenzene reduction, coupled with the pKa-modulated redox potential of the piezoelectric catalyst (for further details, refer to the mechanism exploration section in the SI).

Reaction scope

With the optimal conditions established for both the pathways, we next explored the scope of the mechanochemical reduction of nitro(hetero)arenes to anilines. As shown in Scheme 1, the reduction of 1 bearing various electron-donating functional groups (–Me, –Et, –SMe, –OMe, –OH, –naphthyl and –phenyl) yielded corresponding anilines in up to 98% yield and 99% selectivity. The negligible variation in yields (93% for 2b, 96% for 2c, 94% for 2d) from para-, meta-, and ortho-substituted nitroarenes (1b, 1c, 1d) indicated the absence of significant steric effects. Furthermore, the reduction of nitroarenes with various halide atoms, including chloro 1k–1m, bromo 1n, fluoro 1o and iodo 1p, were well tolerated, providing the corresponding products 2k–2p in yields ranging from 94%–98%. Aryl fragments with –CF3, –OCF3, –C(O)Me, –CN, –alkene and –alkyl at para positions also performed well, yielding the corresponding products 2q–2v in yields ranging from 92%–98%. Also, this reaction tolerated various bifunctional aryl fragments, such as 1w–1y, to afford the corresponding products 2w–2y in good yields. It also achieved a dinitro compound (2z) in moderate yield. The reaction of heteroaryl halides derived from pyridine and quinoline led to the formation of 2aa, 2ab and 2ac with yields of 86%, 80% and 84%, respectively. This method successfully synthesized 2ad and 2ae (up to 92% yield), which are bioactive molecules with potential as antiviral and antidiabetic drugs.
image file: d5gc02613j-s1.tif
Scheme 1 Synthesis of aniline. Reaction conditions: substrate (0.3 mmol), tet-BaTiO3 (1.3 mmol) and MeOH (500 μL) in a stainless-steel milling jar (20 mL) with 20 stainless-steel balls (diameter: 5 mm) at room temperature under air at 45 Hz. Isolated yields. a[thin space (1/6-em)]4 h, b[thin space (1/6-em)]3.5 h, c[thin space (1/6-em)]8 h.

To evaluate the versatility of this switchable divergent mechanochemical reduction system for nitroarenes toward azoxybenzene formation, we systematically investigated the substrate scope with various substituents. As shown in Scheme 2, under standard conditions B (Table 1, entry 7), nitroarenes bearing diverse substituents on the aromatic ring underwent smooth transformation, affording the corresponding products (3a–3l) in moderate to excellent yields (65%–82%) with exclusive selectivity. The reaction demonstrated good compatibility with both electron-donating groups (methyl, methoxy, and tert-butyl; 3a–3f) and electron-withdrawing groups (chloro, fluoro, and trifluoromethoxy; 3g–3i). Notably, alkynyl-substituted derivative (3j) and polysubstituted arenes (3k and 3l) with potential for late-stage functionalization exhibited remarkable reactivity, achieving yields of 65%–82%. The practicality of this method was demonstrated by the gram-scale syntheses of 2a and 3a, achieving yields of 92% and 90%, respectively, in a 4.0 mmol scale reaction.


image file: d5gc02613j-s2.tif
Scheme 2 Synthesis of azoxybenzene and gram-scale reactions. Reaction conditions: substrate (0.3 mmol), tet-BaTiO3 (1.2 mmol), NaOH (0.3 mmol) and isopropanol (400 μL) in a stainless-steel milling jar (20 mL) with 20 stainless-steel balls (diameter: 5 mm) at room temperature under air at 45 Hz. Isolated yields. a[thin space (1/6-em)]4 h, b[thin space (1/6-em)]3 h, c[thin space (1/6-em)]3.5 h. d[thin space (1/6-em)]1a (4 mmol), tet-BaTiO3 (13 mmol) and MeOH (4 mL) in a stainless-steel milling jar (20 mL) with 80 stainless-steel balls (diameter: 5 mm) at room temperature under air at 45 Hz. e[thin space (1/6-em)]1a (5 mmol), tet-BaTiO3 (12 mmol), NaOH (3 mmol) and isopropanol (4 mL) in a stainless-steel milling jar (20 mL) with 80 stainless-steel balls (diameter: 5 mm) at room temperature under air at 45 Hz.

To further investigate the reaction mechanism of piezocatalytic reduction of aromatic nitro compounds to amines using tet-BaTiO3, nitrobenzene was selected as a model compound for the mechanistic studies. Under optimal reaction conditions, electron scavengers (AgNO3 and CCl4) and hole scavengers (TEA and ASA) were introduced into the reaction system. The experimental results are shown in Fig. 2a. It was observed that under standard conditions, nitrobenzene was completely converted with a 97% yield after 4 hours. However, the reaction was almost completely quenched upon the addition of electron scavengers. Similarly, the conversion rate and yield were significantly suppressed when hole scavengers were added. This indicates the critical involvement of electrons and holes in the tet-BaTiO3-mediated piezocatalytic reduction of nitrobenzene to aniline. Analogous experimental results were obtained for the reduction of nitrobenzene to azoxybenzene (Fig. 2b). Additionally, isotopic labeling experiments were conducted by replacing methanol with deuterated methanol in the system, yielding deuterium-labeled aniline. Through a chromogenic reaction with formaldehyde, it was confirmed that methanol was oxidized to formaldehyde after donating hydrogen (Fig. 2c and Fig. S1–2).


image file: d5gc02613j-f2.tif
Fig. 2 Reduction of nitrobenzene to aniline (a) and azoxybenzene (b) with electron scavengers and hole scavengers. (c) Isotopic labeling experiments and formaldehyde detected reaction. (d) Reaction with aniline, nitrobenzene, nitrosobenzene, azoxybenzene or hydrazobenzene as the reagent.

We further investigated the reduction pathway for the hydrogenation of nitrobenzene to azoxybenzene. When using aniline as the starting reactant, no catalytic activity was observed, indicating that the tet-BaTiO3 piezoelectric catalytic system cannot oxidize aniline back to nitrobenzene or azoxybenzene. When nitrosobenzene served as the reactant, the primary product obtained was azoxybenzene (Fig. 2d, entry 3). This suggested the reaction may proceed either through the dehydration of nitrosobenzene and phenylhydroxylamine to form azoxybenzene or via the dimerization and reduction of nitrosobenzene (Fig. 3e, path 2).24 When azoxybenzene was used as the substrate, prolonging the reaction time enabled further reduction reactions, generating azobenzene and hydrazobenzene. These experiments collectively validated that the piezocatalytic reductive amination process aligned with our proposed mechanism (Fig. 3e).


image file: d5gc02613j-f3.tif
Fig. 3 (a) Band gap for tet-BaTiO3. (b) Mott–Schottky plot for tet-BaTiO3. (c) Mott–Schottky plot for tet-BaTiO3 and NaOH. (d) Band position of tet-BaTiO3 and tet-BaTiO3 with NaOH together with selected redox potentials. (e) Proposed mechanism.

The hydride donor property and the band position of the piezoelectric material were the primary factors influencing the reaction selectivity. When the proton source was switched from methanol to isopropanol, azoxybenzene (AXB) formation was observed. Conversely, using methanol as the proton source yielded exclusively aniline as the product, regardless of the base addition. This outcome was attributed to the reduction of the nitrosobenzene dimer by the iso-propoxide anion, a reaction that does not take place with methanol. As shown in prior studies, isopropanol has diminished proton-donating capacity and hole-quenching efficiency relative to methanol.25 Consequently, methanol promoted a faster proton-coupled electron transfer (PCET) rate, thereby favoring aniline formation. Furthermore, hydride transfer mediated by the isopropoxide anion in solution is likely much faster than the reduction of nitrosobenzene by the electrons from tet-BaTiO3 as the latter process is constrained to the surface of tet-BaTiO3.26,27

The addition of an alkali significantly increased the yield of azoxybenzene. This enhancement was attributed to a negative shift in the flat-band potential of tet-BaTiO3 under alkaline conditions.28 In order to further explore the mechanism, the energy band structure of tet-BaTiO3 was explored. The energy of the optical bandgap (Eg) of tet-BaTiO3 was determined by the Kubelka–Munk function in the range of diffuse reflectance spectra. Fig. 3a illustrates the evolution of (αhν)2 as a function of photon energy (hν). Linearly extrapolating this curve with the energy axis ((αhν)2 = 0) gives the bandgap energy value Eg. The value of the band gap energy (tet-BaTiO3) was determined as 3.28 eV. To further explore the band structure of tet-BaTiO3 in alkali-free and alkaline conditions, its corresponding conduction band (CB) positions were evaluated by electrochemical Mott–Schottky measurements. The M–S plot of tet-BaTiO3 displayed a positive slope (Fig. 3b and c), corresponding to a typical n-type semiconductor behavior. It is well known that the CB position is close to the flat band potential for an n-type semiconductor.29 Consequently, the CB position of tet-BaTiO3 in alkaline conditions was fitted at −1.35 V vs. SCE (corresponding to −0.11 V vs. NHE), which was more negative than the CB position of tet-BaTiO3 in alkali-free conditions (−0.51 V vs. NHE), suggesting that tet-BaTiO3 in alkaline conditions has a stronger reduction ability. This value was also more negative than the reduction potentials for converting nitrobenzene to azoxybenzene (−0.78 V vs. SCE) and azobenzene (−0.80 V vs. SCE) (Fig. 3d).9 This indicated that, under alkaline conditions, the catalyst can reduce nitrobenzene to azoxybenzene and azobenzene. However, azobenzene formation was not observed in our system. The reduction potential for converting azoxybenzene to azobenzene was approximately −0.86 V vs. NHE (calculated from the NB/AXB and NB/AB reduction potentials; see SI). This value was more negative than the preceding step's potential (−0.78 V vs. NHE), demonstrating that the reduction of azoxybenzene to azobenzene is thermodynamically less favorable and therefore kinetically slower than the reduction of nitrobenzene to azoxybenzene (Fig. 3e). Supporting this, control experiments using azoxybenzene as the starting material showed that complete reduction to azobenzene is achievable under prolonged reaction times, albeit with slower kinetics (Fig. 2d).

Green chemistry metric evaluation

To validate the present work from a sustainability perspective, we evaluated it using green metric tools such as the E-factor, atom economy (AE), reaction mass efficiency (RME), optimum efficiency (OE), and atom efficiency (AEf). The calculated E-factor values were as low as 0.44 for the 2a–2ae series of compounds and 0.42 for the 3a–3l series. For the preparation of arylamines with higher molecular weights and greater complexity, the E-factor will decrease further. This highlights that the product formation generates minimal waste and demonstrates the eco-compatibility of the current protocol. The excellent OE values—up to 98% for the 2a–2ae series and 88% for the 3a–3l series—illustrated the high efficiency of the protocol. Notably, the excellent values of AE, RME, and AEf further supported this conclusion. For detailed calculations, see the SI (Tables S7 and S8).30

Experimental

Procedures for the reduction of nitroarenes to anilines and azoxybenzenes

To a 20 mL stainless-steel milling jar, 20 stainless-steel balls, nitroarene (0.3 mmol), the mechanocatalyst (1.3 mmol), and a proton donor (400 μL isopropanol or 500 μL MeOH) (for the synthesis of azoxybenzenes, 0.3 mmol NaOH was added) were added. The jar was closed and securely fitted to the mill, which was set for a reaction time of 4 h at a frequency of 45 Hz. Upon completion, the jar was opened and the powder was collected. The mixture was purified by flash column chromatography (SiO2, PE/EtOAc) to obtain the target product. The spectral data matched those reported in the literature.

Conclusions

We present a switchable mechanocatalytic strategy for the selective reduction of nitroarenes to either anilines or azoxybenzenes under mild conditions using cost-effective and environmentally benign perovskite catalysts. Through systematic optimization of the mechanocatalysts, proton donor, and additives, we identified two distinct reaction pathways that enabled precise control over the product selectivity and reactivity, addressing a long-standing synthetic challenge in the conversion of nitroarenes to these target compounds. Mechanistic investigations revealed that the transformation was governed by a synergistic interplay by (1) modulating the proton donor and changing the alkoxyl anion to regulate the reaction pathway and steer the formation of specific reduction products and (2) tailoring the redox potentials of the mechanocatalyst to meet the reduction requirements. This work establishes the first mechano-force-driven platform for selective nitroarene reduction, significantly expanding the scope of reductive amination and advancing the mechanocatalytic reduction methodologies. The breakthrough not only demonstrates the potential of mechanocatalysis in addressing complex organic transformations but also highlights its capacity to enable challenging selectivity control. We anticipate this approach will inspire advancements in selective nitroarene reduction systems, offering versatile options for the selective preparation of anilines and azoxybenzenes from nitroarenes. More broadly, this mechanocatalytic system exemplifies the dynamic modulation of the catalyst redox properties within piezocatalytic environments, showcasing the powerful convergence of mechanochemistry and electrochemical principles. It provides innovative solutions to the persistent challenges in selective reductive amination while opening new avenues for mechanochemical innovation in organic synthesis.

Author contributions

The manuscript was written through contributions from all the authors.

Conflicts of interest

There are no conflicts to declare.

Data availability

The data underlying this study are available in the manuscript and its SI: materials, methods, experimental details, Table S1–S8, Figure S1 and S2 and NMR spectra for all compounds. See DOI: https://doi.org/10.1039/d5gc02613j.

Acknowledgements

We are grateful for the financial support from the National Natural Science Foundation of China (22076122) and Shanghai government (19SG42, 25ZR1402415, 23010504000 and 22ZR1480200).

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Footnote

† These authors contributed equally.
This journal is © The Royal Society of Chemistry 2025
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