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. 2026 Feb 6;12(6):eaeb7677. doi: 10.1126/sciadv.aeb7677

Electrochemically deuterated silane synthesis with D2O

Chao Gao 1, Min Liu 1, Youai Qiu 1,2,3,*
PMCID: PMC12880539  PMID: 41650274

Abstract

Deuterium-labeled silanes are of great significance in organic synthesis and drug discoveries, yet obtaining versatile deuterated silanes efficiently and selectively under electrochemical conditions using green deuterium sources remains enormously challenging. Herein, facile and general electrochemical deuteration of silanes using D2O as the economical deuterium source was reported. A variety of alkyl- and aryl-substituted silanes can be smoothly converted into the corresponding products with excellent levels of deuterium incorporation and yields. Furthermore, this protocol enables 10-gram-scale preparation under high current conditions, underscoring the potential in industry applications. Mechanistic studies have revealed that a catalytic amount of nickel may form a pivotal silicon-nickel intermediate, reversing the polarity of silicon and thereby facilitating the subsequent reactions.

The electrochemical deuteration of silanes proceeds with D2O as the deuterium source, driven by silicon-nickel intermediates.

INTRODUCTION

Deuterium-labeled compounds are vital in organic synthesis (1–3), mechanistic studies (4, 5), mass spectrometry analysis (6, 7), and drug development (8, 9). Among the wide range of deuterated reagents, deuterated silanes exhibit extensive applicability for not only reducing unsaturated compounds (e.g., aldehydes, ketones, nitriles, and alkenes) but also acting as crucial molecular probes to investigate the mechanisms of organic reactions by introducing a deuterium atom (10–15). Thus, the development of deuterated silanes is still in high demand. Traditionally, deuterated silanes have been prepared by the reduction of halosilanes with LiAlD4 or NaBD4. In recent years, transition metal–catalyzed Si─H/D isotope exchange protocols for silanes, with D2 or C6D6 as deuterium sources, have also been reported (16–25). Nevertheless, metal deuterating agents suffer from high cost and strong basicity, imposing stringent demands on reaction equipment. D2 as a deuterium source poses inherent challenges of difficult transportation and the requirement for high pressure–resistant reactors; C6D6 is not only recalcitrant to degradation but also relatively expensive. Wu and co-workers (26) effectively reduced the reaction cost of synthesizing deuterated silanes via a photochemical strategy, with thiols as hydrogen atom transfer agents and deuterium oxide (D2O) as a more economical and environmentally benign deuterium source (Fig. 1A). Recently, electrochemical strategies have attracted great attention because of their advantages, such as tunable electrode potential, avoidance of exogenous chemical oxidants/reductants, and feasibility for industrial-scale production (27–57). These merits have motivated extensive research into electrochemical deuteration protocols. However, the state of the art in electrochemical deuteration with D2O as the economical deuterium source mainly focuses on the construction of C─D bonds (Fig. 1B, left) (58–78). In sharp contrast, the electrochemical construction of Si─D bonds remains elusive and challenging because it suffers from the following: (i) the highly prone self-coupling of silicon radicals/anions under electroreductive conditions; (ii) silicon cations are highly susceptible to nucleophilic attack (e.g., by H2O to form silanols) under electrooxidative conditions, exhibiting high oxophilicity (Fig. 1B, right). Meanwhile, given the significance of deuterated silanes, the development of general and greener electrochemical methods to access diverse deuterated silanes using economical and environmentally benign deuterium sources (e.g., D2O) remains highly desirable.

Fig. 1. Silane deuteration and electrochemically deuterated silane synthesis with D2O.

Fig. 1.

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(A) Reported approaches for deuterated silanes. (B) State of the art in electrochemical deuteration with D2O. (C) Our design for constructing Si─D bonds. (D) This work: Electrochemically deuterated silane synthesis with D2O.

Building on our group’s previous work and prior research reports (77, 79–81), we hypothesized whether D2O can be directly used for the transformation by silyl anions or polarity-inverted silyl metal species generated under electrochemical conditions, and we envisioned two potential electrochemical approaches for the construction of Si─D bonds (Fig. 1C). In path I, we envisaged chlorosilane as the silicon precursor (Fig. 1C, path I), and then a silyl anion is generated under electroreduction conditions and attacks D2O to yield deuterated silane. Unfortunately, after preliminary studies, the predominant product was the dechlorinated self-coupling product of chlorosilane, along with unreacted starting material. We speculated that instantaneous self-coupling occurred during the reduction of chlorosilane to a silicon radical on the surface of the cathode. Alternatively, silane is used as the silicon precursor (Fig. 1C, path II), and the challenge would be reversing the polarity of silicon and reacting with D2O to avoid the formation of silicon radicals and their instantaneous self-coupling or even the silicon cations that are prone to oxygen affinity. To our delight, when a catalytic amount of nickel was added under electrochemical conditions, the desired product was selectively obtained with only a small amount of silanol by-product detected, prompting us to carry out subsequent in-depth studies.

Driven by our continuous interest in electrochemical deuteration reactions (75–78), herein, we put our efforts into moving this transformation forward by realizing the electrochemical synthesis of deuterated silanes with D2O (Fig. 1D). Notable features of this strategy include the following: (i) effective electrochemical synthesis of deuterated silanes; (ii) nickel-induced umpolung reactivity; (iii) excellent deuterium incorporation (D-inc) and broad substrate scope; (iv) D2O as an economical deuterium source; (v) 10-g-scale preparation and tolerating high current, demonstrating the practicality of this method.

RESULTS

Screening of reaction conditions

We initially used methyldiphenylsilane (1a) as the model substrate to explore the reaction conditions for this deuteration process of substituted silanes with D2O under a constant current. To our delight, after systematic optimization, the silane-D product 1 could be obtained in a 93% isolated yield and 95% deuterium incorporation using Ni(COD)2 as a catalyst and L1 [4,4′-di-tert-butyl-2,2′-bipyridine (dtbbpy)] as a ligand under a constant current (10 mA) in the solvent ethyl acetate (EtOAc), with an Al plate used as the anode, cheap graphite felt (GF) used as the cathode, and tetrabutylammonium perchlorate (TBAClO4) as a supporting electrolyte (Fig. 2, entry 1). Variations from the optimized conditions all led to lower yields or deuterium incorporations. First, nickel catalysts were screened, where the result of NiBr2·dme showed a yield of 91% and 93% D-inc, Ni(OTf)2 gave 91% D-inc but a lower yield, and the result of using Ni(Br)2(PPh3)2 was worse (Fig. 2, entries 2 to 4). Then, different ligands were tested. Bipyridine ligands such as ─OMe instead of ─tBu-substituted 2,2′-bpy (L3) showed an 81% yield and 91% D-inc, while ─NH2 instead of ─tBu-substituted 2,2′-bpy (L4) showed a 77% yield but 16% D-inc, and 1,10-phenanthroline (L2) showed no deuterium incorporation (Fig. 2, entry 5). By investigating the effect of the solvents on the transformation, we observed that when EtOAc was replaced with DMF (N,N-dimethylformamide), DME (1,2-dimethoxyethane), or NMP (N-methyl-2-pyrrolidone), the yields of 1 plunged from 93% to trace amounts, and 1,4-dioxane gave 90% D-inc but only a 10% yield (Fig. 2, entries 6 and 7). When we changed the electrolyte TBAClO4 with TBABF4 (tetrabutylammonium tetrafluoroborate) or TBAI (tetrabutylammonium iodide), a product with 92% D-inc and a 79 or 84% yield could be obtained. Although TBAOAc (tetrabutylammonium acetate) gave 1 in an 86% yield, the deuterium incorporation was 78% (Fig. 2, entries 8 to 10). Subsequently, several electrode materials were investigated, and Al (+)|GF (−) was proven to be optimal. When the cathode was replaced with Pt or Pb, neither showed better performance than GF (Fig. 2, entries 11 and 12). In addition, we found that this system was sensitive to air, as when exposed to it, it only gave an 85% yield and 68% D-inc of product 1 (Fig. 2, entry 13). The control experiment proved the essential role of electricity, as no deuterated products could be obtained in its absence (Fig. 2, entry 14). Last, we also used chloro(methyl)diphenylsilane (1b) as the silicon precursor to explore the conditions, and the predominant product was the dechlorinated self-coupling product of 1b along with unreacted starting material (Fig. 2, entry 15).

Fig. 2. Screening of the reaction conditions.

Fig. 2.

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Reaction conditions: undivided cell, Al plate anode, GF plate cathode, constant current of 10 mA, 1a (0.4 mmol), D2O (20 mmol, 50 equiv), Ni(COD)2 (10 mol %), dtbbpy (20 mol %), TBAClO4 (0.4 mmol, 1.0 equiv), EtOAc (4 ml), Ar, room temperature (rt.), 13 hours. *Isolated yields of the S─D/H mixtures. †Ratios determined by 1H NMR spectroscopy. h, hours; CCE, constant current electrolysis; TBABF4, tetrabutylammonium tetrafluoroborate; TBAI, tetrabutylammonium iodide; TBAOAc, tetrabutylammonium acetate; DMF, N,N-dimethylformamide; DME, 1,2-dimethoxyethane; NMP, N-methyl-2-pyrrolidone.

Substrate scope

With the optimal conditions established, the scope of substituted silanes was explored (Fig. 3). First, a series of diphenylsilanes bearing different substituents at the para-position, including electron-donating and electron-withdrawing groups, were investigated in the transformation. To our delight, all of the substrates gave the desired products in good yields and with good levels of deuterium incorporation (2 to 7, 70 to 91%, 92 to 95% D-inc). Substrates with two naphthyl groups could also be smoothly converted to the desired product with a moderate yield and high deuterium incorporation (8). Next, the impact of steric hindrance on the transformation was investigated. The substrate including two meta-groups showed good performance during the electrolysis process (9, 81%, 93% D-inc). Then, we explored the replacement of the substituted alkyl group in the substrates from methyl to ethyl or even the more sterically hindered tert-butyl. Delightfully, both of the substrates were successfully converted into the corresponding products (10 and 11). Aryl-substituted silanes, including diarylsilanes with different steric and electronic properties, were well tolerated to afford the corresponding products with excellent D-inc (12 to 19). In addition, di-alkylsilanes proceeded well in the transformation (20 and 21). Gratifyingly, tri-alkyl–substituted silanes with different amounts of steric hindrance such as n-propyl, isopropyl, n-butyl, and n-hexyl were compatible with this reaction, furnishing the desired products in good yields and with good to excellent D-inc (22 to 25). Disilanes such as 1,4-bis(dimethylsilyl)benzene were also suitable for the system, which smoothly provided the desired product with two deuterium atoms incorporated (26, 66% yield, 88% D-inc). Notably, dihydrosilane substrates could also undergo the corresponding transformation via our strategy despite the relatively low yields (27 and 28), while trihydrosilane may undergo overelectrolysis in our system because of its high reactivity (29).

Fig. 3. Scope of alkyl/aryl–substituted silanes.

Fig. 3.

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Reaction conditions: undivided cell, Al plate anode, GF plate cathode, constant current of 10 mA, 1a (0.4 mmol), D2O (20 mmol, 50 equiv), Ni(COD)2 (10 mol %), dtbbpy (20 mol %), TBAClO4 (0.4 mmol, 1.0 equiv), EtOAc (4 ml), Ar, rt., 13 hours. *Isolated yields of the Si─D/H mixtures. †Ratios determined by 1H NMR spectroscopy. ‡NiBr2·dme (10 mol %). §NiBr2·dme (10 mol %) and constant current of 7 mA. N.D., not detected.

Encouraged by the aforementioned results, we further investigated the substrate scope of triaryl-substituted silanes in the system, including tert-butyl, electron-donating groups [─OMe, ─OBn, and ─N(Me)2], and electron-withdrawing groups (─CO2Et, ─F, and ─CF3), at the para-position of one of the benzene rings (Fig. 4A). Gratifyingly, all of the substrates efficiently converted into the corresponding deuterated products (31 to 38). Other substrates, such as those with a phenyl group or a nitrogen/oxygen–containing heterocycle at the para-position of the benzene ring, were both well tolerated (39 and 40). Subsequently, we tested substrates with methoxy or halogen at the meta-position of the benzene ring, all of which afforded the desired products (41 and 42). Furthermore, several specific aryl systems were tested. When benzo[d][1,3]dioxole, naphthalene, and dibenzo[b,d]furan were introduced as aryl groups in the substrates, all of them were well tolerated and showed good performance (43 to 45). In addition, substrates in which each of the three benzene rings was monosubstituted worked smoothly in the reaction system (46 and 47). It was worth noting that our protocol was also efficient for triphenylgermane and the corresponding product could be successfully obtained (48, 65% yield, 90% D-inc). Inspiringly, some complex molecules containing ketals, halogens, and N-Boc groups were all amenable to the electrochemical deuteration process, delivering the desired deuterated products in moderate to good yields and excellent D-inc (49 to 52). These results indicate that this electrochemical deuteration strategy holds great promise for the synthesis of deuterated silane compounds.

Fig. 4. Scope of triaryl-substituted silanes and derivative applications.

Fig. 4.

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Reaction conditions: undivided cell, Al plate anode, GF plate cathode, constant current of 10 mA, 1a (0.4 mmol), D2O (20 mmol, 50 equiv), Ni(COD)2 (10 mol %), dtbbpy (20 mol %), TBAClO4 (0.4 mmol, 1.0 equiv), EtOAc (4 ml), Ar, rt., 13 hours. *Isolated yields of the Si─D/H mixtures. †Ratios determined by 1H NMR spectroscopy. ‡NiBr2·dme (10 mol %). §NiBr2·dme (10 mol %) and constant current of 7 mA. D2O (40 mmol, 100 equiv). (A) Triaryl-substituted silanes and late-stage deuteration of complex molecules. (B) Gram/10-g-scale preparations. (C) Prices of Si─H versus Si─D reagents. (D) Derivative applications.

Gram/10-g-scale experiments

To highlight the practicality of our synthetic approach, we attempted to carry out gram-scale experiments to synthesize products 1 and 20. The expected product 1 was obtained in a 75% yield (1.49 g) and 96% D-inc (for details, please see the Supplementary Materials), and product 20 was obtained in a 73% yield (1.10 g) and 95% D-inc under a constant current of 100 mA in 24 hours. We also conducted an 80-mmol-scale experiment to synthesize product 1, and unexpectedly, we obtained the product in a 68% yield (10.8 g) and 87% D-inc under a constant current of 300 mA in 48 hours (Fig. 4B). The results and comparisons of commercially available prices of Si─H and Si─D reagents (Fig. 4C) illustrate the practicality and efficiency of this electrochemical deuteration protocol.

Derivative applications

In addition, we performed some deuterium derivatizations using 1 as the reducing agent and B(C6F5)3 as the Lewis-acid catalyst (Fig. 4D). To our delight, we obtained the corresponding products of arylolefins, aldehydes, ketones, and vanillin acetate in effective deuterium incorporation and good yields (53 to 56), which further confirms the practicality of this electroreduction strategy.

Mechanistic investigations

To gain insights into the mechanism of this electrochemical protocol, we carried out a series of mechanistic experiments, among which control experiments were first performed. Product 1 was not able to be obtained without electricity. Next, we found that the yield of product 1 sharply decreased to 43% when there was no dtbbpy present in the system. In addition, it only gave the starting material in recovery of 78% without Ni(COD)2 or 57% without Ni(COD)2 and dtbbpy (Fig. 5A). Meanwhile, we also conducted stoichiometric metal catalysis experiments under nonelectrified conditions, and no deuterated products were detected (for details, please see the Supplementary Materials, page S22). These results indicate that both electricity and Ni(COD)2 are of crucial importance during the reaction process. Also, the ligand dtbbpy exerts a notable effect on the transformation. It is hypothesized that the substrate is highly probable to form a silicon-nickel intermediate with the nickel metal during the reaction, and the application of electricity promotes cycling of nickel metal through its valence states. In addition, divided cell experiments were conducted, and we obtained 1 (62%, 66% D-inc) in the cathodic chamber, while no target product was detected in the anodic chamber, suggesting that our strategy involved an electrochemical reduction process occurring at the cathode (for details, please see the Supplementary Materials, page S27). Furthermore, a reversible D/H exchange experiment was performed using 1 (96% D-inc). Notably, the reversible reaction proceeded smoothly, affording the target product with an 83% yield and 15% D-inc (Fig. 5B). The retention of 15% deuterium in the product further indicates that silicon-deuterium bonds exhibit greater stability and higher resistance to cleavage compared to silicon-hydrogen bonds. Simultaneously, we used compounds 1a and 1 as starting materials to investigate their H/D and D/H exchange rates, respectively, and fitted the data into curves (Fig. 5C). As illustrated in the graphs (Fig. 5C), linear regression was performed on the curves, and the average slopes were calculated. The average slope (K) of the H/D exchange rate curve was greater than that of the D/H exchange rate curve, which is consistent with our hypothesis and the results of the aforementioned reversible experiment. This finding further confirms that silicon-deuterium bonds exhibit higher stability and greater resistance to cleavage relative to silicon-hydrogen bonds.

Fig. 5. Mechanistic experiments and plausible mechanisms.

Fig. 5.

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(A) Control experiments. (B) D/H exchange experiment. (C) H/D and D/H exchange rate studies. (D) Kinetic experiments. (E) Cyclic voltammetry experiments using glass carbon as the working electrode, Pt plate as the counter electrode, and Ag/AgCl as the reference electrode under Ar. (F) Proposed mechanism.

In addition, we conducted kinetic experiments on varying equivalents of D2O, Ni(COD)2, and dtbbpy. Simultaneously, we performed linear fitting on the obtained data and calculated the average slopes (Fig. 5D). The results demonstrate that variations in the quantities of D2O, Ni(COD)2, and the ligand dtbbpy each have measurable effects on the deuterium incorporation rate of the products. Among these factors, the catalyst Ni(COD)2 exhibits the most pronounced impact, consistent with the outcomes of the aforementioned control experiment. This concordance further validates the catalyst’s critical role during the electrolysis process.

To gain further exploration into the mechanism of the electroreductive protocol, in-depth studies were carried out through detailed cyclic voltammetry experiments. As shown in Fig. 5E, the nickel complex NiBr2·dtbbpy exhibited two reduction peaks at −1.33 and −1.90 V versus Ag/AgCl (Fig. 5E, blue line), corresponding to the reduction of [Ni]II/[Ni]I and [Ni]I/[Ni]0, respectively. When a small amount of 31a was continuously added, a slight increase in the reduction peak of [Ni]I/[Ni]0 was observed in the cyclic voltammogram, while the oxidation peak of Ni0 (−1.74 V versus Ag/AgCl) gradually disappeared, suggesting that [Ni]0 could undergo an oxidative addition with silanes. The phenomenon was more pronounced in correlation with the amount of 31a (for details, please see fig. S12), which may be attributed to the greater consumption of [Ni]0 via oxidative addition with more substrate 31a. This is consistent with an electrochemical/chemical mechanism (82), indicating that a silylnickel intermediate is likely generated in the system through the interaction of the silane with the nickel catalyst, thereby facilitating the reaction.

On the basis of the mechanistic experiments, cyclic voltammetry studies, and relevant literature (83–87), a plausible mechanism for this electrochemical deuteration of silanes with D2O was proposed (Fig. 5F). Initially, the aluminum anode lost electrons to form Al3+, with the electrons flowing toward the cathode through the external wire. Then, [Ni]0 generated by the reduction of [Ni]II underwent oxidative addition with silane to form a Si─[Ni]II─H intermediate (Int-1). Subsequently, a Si─[Ni]I intermediate (Int-2) was generated via cathodic reduction of Int-1 and carried out a nucleophilic attack on D2O, thereby providing the desired product. Meanwhile, [Ni]I in the system was reduced again to [Ni]0 by gaining an electron at the cathode, thus completing the entire catalytic cycle.

DISCUSSION

In conclusion, an electrochemical strategy for the synthesis of deuterated silanes with D2O as an easily handled and inexpensive deuterium source has been successfully developed. The method shows excellent D-inc and a broad substrate scope, which is also distinguished by nickel-induced umpolung reactivity, and utilization of electricity as an environmentally friendly reductant. Meanwhile, an example of 10-g-scale preparation and tolerating high current helps to show the potential of this method for industrial synthetic applications. We expect that this facile, cost-efficient, and environmentally friendly electrochemical approach will facilitate its extensive utilization as a key tool in both academic research and industrial applications. Further studies on electrochemical deuteration transformations of various silicon precursors are currently underway in our laboratory.

MATERIALS AND METHODS

General procedure of electrochemically deuterated silane synthesis with D2O

Electrocatalysis was carried out in an undivided cell with an Al plate anode (0.3 mm by 10.0 mm by 20.0 mm) and a GF cathode (5.0 mm by 10.0 mm by 20.0 mm). To a 15-ml oven-dried undivided electrochemical cell equipped with a magnetic bar were added Ni(COD)2 (11.0 mg, 10 mol %), dtbbpy (21.4 mg, 20 mol %), TBAClO4 (0.4 mmol, 1.0 equiv), and silane (0.4 mmol, 1.0 equiv). Then, ultradry EtOAc (4.0 ml) and D2O (370 μl, 50.0 equiv) were added under Ar. Electrocatalysis was performed at room temperature with a constant current of 10.0 mA maintained for 13 hours. The electrodes were washed with EtOAc (3 × 5.0 ml) in an ultrasonic bath, then filtered through celite under reduced pressure with dichloromethane or EtOAc (3 × 15.0 ml), and concentrated in vacuo. The crude product was purified by column chromatography to furnish the desired product.

Acknowledgments

We thank Y. Qiu for insightful guidance and funding acquisition. We thank J. Jia in this group for reproducing the results of 4, 16, and 35. In addition, we acknowledge the assistance of Haihe Laboratory of Sustainable Chemical Transformations and Nankai University.

Funding:

This work was supported by the National Key R&D Program of China (2022YFA1503200), the National Natural Science Foundation of China (grant nos. 22371149 and 22188101), the Natural Science Foundation of Tianjin (24JCJQJC00210), the Fundamental Research Funds for the Central Universities (no. 63224098), the Frontiers Science Center for New Organic Matter, Nankai University (grant no. 63181206), and the open project program of State Key Laboratory of Green Chemical Synthesis and Conversion (grant no. SKLGSC-KF-202502). In addition, the project was also supported by the Open Research Fund of State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University.

Author contributions:

Conceptualization: C.G., M.L., and Y.Q. Methodology: C.G., M.L., and Y.Q. Investigation: C.G., M.L., and Y.Q. Validation: C.G., M.L., and Y.Q. Visualization: C.G., M.L., and Y.Q. Writing—original draft: C.G. and Y.Q. Writing—review and editing: C.G., M.L., and Y.Q. Supervision: C.G., M.L., and Y.Q. Resources: C.G., M.L., and Y.Q. Funding acquisition: Y.Q. Data curation: C.G., M.L., and Y.Q. Formal analysis: M.L. and Y.Q. Project administration: C.G., M.L., and Y.Q. Software: Y.Q.

Competing interests:

The authors declare that they have no competing interests.

Data and materials availability:

All data and code needed to evaluate and reproduce the results in the paper are present in the paper and/or the Supplementary Materials.

Supplementary Materials

This PDF file includes:

Supplementary Text

Figs. S1 to S12

Tables S1 to S15

References

sciadv.aeb7677_sm.pdf (9.7MB, pdf)

REFERENCES

  • 1.Yang X., Ben H., Ragauskas A. J., Recent advances in the synthesis of deuterium-labeled compounds. Asian J. Org. Chem. 10, 2473–2485 (2021). [Google Scholar]
  • 2.Kopf S., Bourriquen F., Li W., Neumann H., Junge K., Beller M., Recent developments for the deuterium and tritium labeling of organic molecules. Chem. Rev. 122, 6634–6718 (2022). [DOI] [PubMed] [Google Scholar]
  • 3.Li H., Shabbir M., Li W., Lei A., Recent advances in deuteration reactions. Chin. J. Chem. 42, 1145–1156 (2024). [Google Scholar]
  • 4.Simmons E. M., Hartwig J. F., On the interpretation of deuterium kinetic isotope effects in C–H bond functionalizations by transition-metal complexes. Angew. Chem. Int. Ed. Engl. 51, 3066–3072 (2012). [DOI] [PubMed] [Google Scholar]
  • 5.Gomez-Gallego M., Sierra M. A., Kinetic isotope effects in the study of organometallic reaction mechanisms. Chem. Rev. 111, 4857–4963 (2011). [DOI] [PubMed] [Google Scholar]
  • 6.Atzrodt J., Derdau V., Pd- and Pt-catalyzed H/D exchange methods and their application for internal MS standard preparation from a Sanofi-Aventis perspective. J. Label. Compd. Radiopharm. 53, 674–685 (2010). [Google Scholar]
  • 7.Atzrodt J., Derdau V., Kerr W. J., Reid M., Deuterium- and tritium-labelled compounds: Applications in the life sciences. Angew. Chem. Int. Ed. Engl. 57, 1758–1784 (2018). [DOI] [PubMed] [Google Scholar]
  • 8.Chen J., Zhu Y.-Y., Zhang S.-S., Gu S.-X., Application of deuterium in research and development of drugs. Eur. J. Med. Chem. 287, 117371 (2025). [DOI] [PubMed] [Google Scholar]
  • 9.Mullard A., Deuterated drugs draw heavier backing. Nat. Rev. Drug Discov. 15, 219–222 (2016). [DOI] [PubMed] [Google Scholar]
  • 10.Li K., Nie M., Tang W., Synthesis of α-tertiary allylsilanes by palladium-catalyzed hydrosilylation of 1,1-disubstituted allenes. Green Synth. Catal. 1, 171–174 (2020). [Google Scholar]
  • 11.Si Y., Liu Y., Zhou F., Fang L., Wu K., Luan Y.-X., Chen L., Tang P., Cobalt-catalyzed enantioselective hydrotrifluoromethoxylation of aromatic alkenes. Angew. Chem. Int. Ed. Engl. 64, e202501680 (2025). [DOI] [PubMed] [Google Scholar]
  • 12.Xie F., Zhang S., Yang M., He J., Li S., Zhang Y., Frustrated Lewis pair-promoted organocatalytic transformation of hydrosilanes into silanols with water oxidant. J. Am. Chem. Soc. 146, 29373–29382 (2024). [DOI] [PubMed] [Google Scholar]
  • 13.Wang J.-J., Huang H., Sun H.-L., Yang F., Wen J., Zhu R., Mimicking hydrogen-atom-transfer-like reactivity in copper-catalysed olefin hydrofunctionalization. Nat. Catal. 7, 838–846 (2024). [Google Scholar]
  • 14.Wang C., Wang X., Wang Z., Wang X., Ding K., Nickel catalyzed enantioselective 1,4-hydroamination of 1,3-dienes. J. Am. Chem. Soc. 146, 18440–18450 (2024). [DOI] [PubMed] [Google Scholar]
  • 15.He P., Guan M.-H., Hu M.-Y., Zhou Y.-J., Huang M.-Y., Zhu S.-F., Iron-catalyzed allylic C(sp3)−H silylation: Spin-crossover-efficiency-determined chemoselectivity. Angew. Chem. Int. Ed. Engl. 63, e202402044 (2024). [DOI] [PubMed] [Google Scholar]
  • 16.Schmidt D., Zell T., Schaub T., Radius U., Si–H bond activation at {(NHC)2Ni0} leading to hydrido silyl and bis(silyl) complexes: A versatile tool for catalytic Si–H/D exchange, acceptorless dehydrogenative coupling of hydrosilanes, and hydrogenation of disilanes to hydrosilanes. Dalton Trans. 43, 10816–10827 (2014). [DOI] [PubMed] [Google Scholar]
  • 17.Komuro T., Osawa T., Suzuki R., Mochizuki D., Higashi H., Tobita H., Silyl–pyridine–amine pincer-ligated iridium complexes for catalytic silane deuteration via room temperature C–D bond activation of benzene-d6. Chem. Commun. 55, 957–960 (2019). [DOI] [PubMed] [Google Scholar]
  • 18.Linford-Wood T. G., Mahon M. F., Grayson M. N., Webster R. L., Iron-catalyzed H/D exchange of primary silanes, secondary silanes, and tertiary siloxanes. ACS Catal. 12, 2979–2985 (2022). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 19.Fortman G. C., Jacobsen H., Cavallo L., Nolan S. P., Catalytic deuteration of silanes mediated by N-heterocyclic carbene-Ir(III) complexes. Chem. Commun. 47, 9723–9725 (2011). [DOI] [PubMed] [Google Scholar]
  • 20.Campos J., Esqueda A. C., Lopez-Serrano J., Sánchez L., Cossio F. P., de Cozar A., Alvarez E., Maya C., Carmona E., A cationic Rh(III) complex that efficiently catalyzes hydrogen isotope exchange in hydrosilanes. J. Am. Chem. Soc. 132, 16765–16767 (2010). [DOI] [PubMed] [Google Scholar]
  • 21.Kratish Y., Bravo-Zhivotovskii D., Apeloig Y., Convenient synthesis of deuterosilanes by direct H/D exchange mediated by easily accessible Pt(0) complexes. ACS Omega 2, 372–376 (2017). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 22.Smart K. A., Mothes-Martin E., Annaka T., Grellier M., Sabo-Etienne S., Silane deuteration catalyzed by ruthenium bis(dihydrogen) complexes or simple metal salts. Adv. Synth. Catal. 356, 759–764 (2014). [Google Scholar]
  • 23.Laglera-Gándara C. J., Jiménez-Rioboó R., Álvarez-Rodríguez L., Peloso R., Ríos P., Rodríguez A., Nickel-catalyzed deuteration of primary, secondary, and tertiary silanes: Scope and mechanistic insights. J. Org. Chem. 90, 5206–5212 (2025). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 24.Wang Y., Qiu F., Yao F., Zeng L., Lei A., Li W., Ru-based nanoparticle catalyzed direct H/D exchange of silanes. Chem. Commun. 61, 6607–6610 (2025). [DOI] [PubMed] [Google Scholar]
  • 25.Esteruelas M. A., Martínez A., Oliván M., Vélez A., A general rhodium catalyst for the deuteration of boranes and hydrides of the group 14 elements. J. Org. Chem. 85, 15693–15698 (2020). [DOI] [PubMed] [Google Scholar]
  • 26.Zhou R., Li J., Cheo H. W., Chua R., Zhan G., Hou Z., Wu J., Visible-light-mediated deuteration of silanes with deuterium oxide. Chem. Sci. 10, 7340–7344 (2019). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 27.Yan M., Kawamata Y., Baran P. S., Synthetic organic electrochemical methods since 2000: On the verge of a renaissance. Chem. Rev. 117, 13230–13319 (2017). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 28.Xiong P., Xu H.-C., Chemistry with electrochemically generated N-centered radicals. Acc. Chem. Res. 52, 3339–3350 (2019). [DOI] [PubMed] [Google Scholar]
  • 29.Anson C. W., Stahl S. S., Mediated fuel cells: Soluble redox mediators and their applications to electrochemical reduction of O2 and oxidation of H2, alcohols, biomass, and complex fuels. Chem. Rev. 120, 3749–3786 (2020). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 30.Novaes L. F. T., Liu J.-J., Shen Y.-F., Lu L.-X., Meinhardt J. M., Lin S., Electrocatalysis as an enabling technology for organic synthesis. Chem. Soc. Rev. 50, 7941–8002 (2021). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 31.Wang Y., Dana S., Long H., Xu Y., Li Y., Kaplaneris N., Ackermann L., Electrochemical late-stage functionalization. Chem. Rev. 123, 11269–11335 (2023). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 32.Shi S., Liang Y., Jiao N., Electrochemical oxidation induced selective C–C bond cleavage. Chem. Rev. 121, 485–505 (2020). [DOI] [PubMed] [Google Scholar]
  • 33.Ma C., Guo J.-F., Xu S.-S., Mei T.-S., Recent advances in asymmetric organometallic electrochemical synthesis (AOES). Acc. Chem. Res. 58, 399–414 (2025). [DOI] [PubMed] [Google Scholar]
  • 34.Zhang W., Liao L.-L., Li L., Liu Y., Dai L.-F., Sun G.-Q., Ran C.-K., Ye J.-H., Lan Y., Yu D.-G., Electroreductive dicarboxylation of unactivated skipped dienes with CO2. Angew. Chem. Int. Ed. Engl. 62, e202301892 (2023). [DOI] [PubMed] [Google Scholar]
  • 35.Zhu C., Ang N. W. J., Meyer T. H., Qiu Y., Ackermann L., Organic electrochemistry: Molecular syntheses with potential. ACS Cent. Sci. 7, 415–431 (2021). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 36.Ackermann L., Metalla-electrocatalyzed C–H activation by Earth-abundant 3d metals and beyond. Acc. Chem. Res. 53, 84–104 (2019). [DOI] [PubMed] [Google Scholar]
  • 37.Wang F., Stahl S. S., Electrochemical oxidation of organic molecules at lower overpotential: Accessing broader functional group compatibility with electron-proton transfer mediators. Acc. Chem. Res. 53, 561–574 (2020). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 38.Xu S.-S., Qiu H., Xie P.-P., Wang Z.-H., Wang X., Zheng C., You S.-L., Mei T.-S., Cobalt-catalyzed electrochemical enantioselective reductive cross-coupling of organohalides. CCS Chem. 7, 245–255 (2025). [Google Scholar]
  • 39.Xing Y.-K., Wang Z.-H., Fang P., Ma C., Mei T.-S., Divergent synthesis of aryl amines and dihydroquinazolinones via electrochemistry-enabled rhodium-catalyzed C–H functionalization. Sci. China Chem. 66, 2863–2870 (2023). [Google Scholar]
  • 40.Chen M., Wu Z.-J., Song J., Xu H.-C., Electrocatalytic allylic C−H alkylation enabled by a dual-function cobalt catalyst. Angew. Chem. Int. Ed. Engl. 61, e202115954 (2022). [DOI] [PubMed] [Google Scholar]
  • 41.Chen P.-Y., Huang C., Jie L.-H., Guo B., Zhu S., Xu H.-C., Unlocking the potential of oxidative asymmetric catalysis with continuous flow electrochemistry. J. Am. Chem. Soc. 146, 7178–7184 (2024). [DOI] [PubMed] [Google Scholar]
  • 42.Li L.-B., Wang X.-Y., Fu N.-K., Electrochemical nickel-catalyzed hydrogenation. Angew. Chem. Int. Ed. Engl. 63, e202403475 (2024). [DOI] [PubMed] [Google Scholar]
  • 43.Tang H.-T., Zhou H.-Y., Pan Y.-M., Zhang J.-L., Cui F.-H., Li W.-H., Wang D., Single-atom manganese-catalyzed oxygen evolution drives the electrochemical oxidation of silane to silanol. Angew. Chem. Int. Ed. Engl. 136, e202315032 (2024). [DOI] [PubMed] [Google Scholar]
  • 44.Bu F., Deng Y., Xu J., Yang D., Li Y., Li W., Lei A., Electrocatalytic reductive deuteration of arenes and heteroarenes. Nature 634, 592–599 (2024). [DOI] [PubMed] [Google Scholar]
  • 45.Li J., Zhang S., Xu K., Recent advances towards electrochemical transformations of α-keto acids. Chin. Chem. Lett. 32, 2729–2735 (2021). [Google Scholar]
  • 46.Wan Q., Liu R.-X., Zhang Z., Wu X.-D., Hou Z.-W., Wang L., Recent advances in the electrochemical defluorinative transformations of C–F bonds. Chin. J. Chem. 42, 1913–1928 (2024). [Google Scholar]
  • 47.DeLano T. J., Reisman S. E., Enantioselective electroreductive coupling of alkenyl and benzyl halides via nickel catalysis. ACS Catal. 9, 6751–6754 (2019). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 48.Kundu G., Lambert T. H., Electrochemical vicinal C–H difunctionalization of saturated azaheterocycles. J. Am. Chem. Soc. 146, 1794–1798 (2024). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 49.Hu P., Peters B. K., Malapit C. A., Vantourout J. C., Wang P., Li J., Mele L., Echeverria P. G., Minteer S. D., Baran P. S., Electroreductive olefin-ketone coupling. J. Am. Chem. Soc. 142, 20979–20986 (2020). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 50.Dong X., Roeckl J. L., Waldvogel S. R., Morandi B., Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations. Science 371, 507–514 (2021). [DOI] [PubMed] [Google Scholar]
  • 51.Wang B., Peng P., Ma W., Liu Z., Huang C., Cao Y., Hu P., Qi X., Lu Q., Electrochemical borylation of alkyl halides: Fast, scalable access to alkyl boronic esters. J. Am. Chem. Soc. 143, 12985–12991 (2021). [DOI] [PubMed] [Google Scholar]
  • 52.Chen S., Shi A., Yang G., Xie P., Liu F., Qiu Y., Electrochemical demethoxyl-cyanation of methoxyarenes via SNAr. Chin. Chem. Lett. 36, 110810 (2025). [Google Scholar]
  • 53.Kou G., Li P., Yang G., Qiu Y., Electrochemical construction of contiguous quaternary centers. CCS Chem. 7, 3005–3014 (2025). [Google Scholar]
  • 54.Shi A., Liu Y., Zhang R., Zhu Z., Qiu Y., Catalyst-free electrochemical SNAr of electron-rich fluoroarenes using carboxylic acids. eScience 4, 100255 (2024). [Google Scholar]
  • 55.Wang Q., Wang Y., Liu M., Chu G., Qiu Y., Recent advances in photochemical/electrochemical carboxylation of olefins with CO2. Chin. J. Chem. 42, 2249–2266 (2024). [Google Scholar]
  • 56.Zeng W., Wang Y., Peng C., Qiu Y., Organo-mediator enabled electrochemical transformations. Chem. Soc. Rev. 54, 4468–4501 (2025). [DOI] [PubMed] [Google Scholar]
  • 57.Li P., Wang Y., Zhao H., Qiu Y., Electroreductive cross-coupling reactions: Carboxylation, deuteration, and alkylation. Acc. Chem. Res. 58, 113–129 (2025). [DOI] [PubMed] [Google Scholar]
  • 58.Renaud R. N., Electrochemical synthesis of deuterio organic compounds. I. Electrochemical reduction of 1-halonaphthalenes and synthesis of 1-chloro-4-methylnaphthalene. Can. J. Chem. 52, 376–380 (1974). [Google Scholar]
  • 59.Kimura M., Miyahara H., Moritani N., Sawaki Y., Electroreductive dehalogenation of chlorinated aromatic ethers. Unexpected electrogenerated base-catalyzed reactions. J. Org. Chem. 55, 3897–3902 (1990). [Google Scholar]
  • 60.Liu C., Han S., Li M., Chong X., Zhang B., Electrocatalytic deuteration of halides with D2O as the deuterium source over a copper nanowire arrays cathode. Angew. Chem. Int. Ed. Engl. 59, 18527–18531 (2020). [DOI] [PubMed] [Google Scholar]
  • 61.Liu X., Liu R., Qiu J., Cheng X., Li G., Chemical-reductant-free electrochemical deuteration reaction using deuterium oxide. Angew. Chem. Int. Ed. Engl. 59, 13962–13967 (2020). [DOI] [PubMed] [Google Scholar]
  • 62.Kurimoto A., Sherbo R. S., Cao Y., Loo N. W., Berlinguette C. P., Electrolytic deuteration of unsaturated bonds without using D2. Nat. Catal. 3, 719–726 (2020). [Google Scholar]
  • 63.Valiente A., Martínez-Pardo P., Kaur G., Johansson M. J., Martín-Matute B., Electrochemical proton reduction over nickel foam for Z-stereoselective semihydrogenation/deuteration of functionalized alkynes. ChemSusChem 15, e202102221 (2022). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 64.Kolb S., Werz D. B., Site-selective hydrogenation/deuteration of benzylic olefins enabled by electroreduction using water. Chem. A Eur. J. 29, e202300849 (2023). [DOI] [PubMed] [Google Scholar]
  • 65.Fan Y., Ou W., Chen M., Liu Y., Zhang B., Ruan W., Su C., Metal-free electrochemically reductive deuteration of C═N bonds with D2O toward deuterated amines. Org. Lett. 25, 432–437 (2023). [DOI] [PubMed] [Google Scholar]
  • 66.Sheng J., Cheng X., Electrochemical mono-deuterodefluorination of trifluoromethyl aromatic compounds with deuterium oxide. CCS Chem. 6, 230–240 (2024). [Google Scholar]
  • 67.Wu Y., Liu C., Wang C., Lu S., Zhang B., Selective transfer semihydrogenation of alkynes with H2O (D2O) as the H (D) source over a Pd-P cathode. Angew. Chem. Int. Ed. Engl. 59, 21170–21175 (2020). [DOI] [PubMed] [Google Scholar]
  • 68.Shi L., Liu M., Zheng L., Gao Q., Wang M., Wang X., Xiang J., Electrochemical γ-selective deuteration of pyridines. Org. Lett. 26, 4318–4322 (2024). [DOI] [PubMed] [Google Scholar]
  • 69.Feng W.-J., Chang Z., Lu X., Fu Y., Electrochemical cobalt-catalyzed semi-deuteration of alkynes to access deuterated Z-alkenes. Nat. Commun. 16, 2390 (2025). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 70.Yan Y., Hao J., Peng Y., Yin M., Jing L., Han P., Electrochemical benzylic deuteration of p-QMs enabling the synthesis of benzylic deuterated diarylmethanes. Org. Biomol. Chem. 22, 4047–4051 (2024). [DOI] [PubMed] [Google Scholar]
  • 71.Qiu F., Chen Y., Liao P., Gao Y., Guo M., Zhang H., Lei A., Li W., Electrochemical selective deuterium labelling of N-heteroarenes. Green Synth. Catal. 6, 003 (2024). [Google Scholar]
  • 72.Singh S., Singh M., Singh A., Singh M. S., Electrochemical debrominative hydrogenation/deuteration of 2-bromo-N-arylacetamides. Chem. Commun. 61, 6478–6481 (2025). [DOI] [PubMed] [Google Scholar]
  • 73.Wood D., Lin S., Deuterodehalogenation under net reductive or redox-neutral conditions enabled by paired electrolysis. Angew. Chem. Int. Ed. Engl. 62, e202218858 (2023). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 74.Shen Z. J., Zhu C., Zhang X., Yang C., Rueping M., Guo L., Xia W., Organoboron reagent-controlled selective (deutero)hydrodefluorination. Angew. Chem. Int. Ed. Engl. 62, e202217244 (2023). [DOI] [PubMed] [Google Scholar]
  • 75.Zhao Z., Zhang R., Liu Y., Zhu Z., Wang Q., Qiu Y., Electrochemical C−H deuteration of pyridine derivatives with D2O. Nat. Commun. 15, 3832 (2024). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 76.Yang K., Feng T., Qiu Y., Organo-mediator enabled electrochemical deuteration of styrenes. Angew. Chem. Int. Ed. Engl. 62, e202312803 (2023). [DOI] [PubMed] [Google Scholar]
  • 77.Wang Y., Wang Q., Wu L., Jia K., Wang M., Qiu Y., Electroreduction of unactivated alkenes using water as hydrogen source. Nat. Commun. 15, 2780 (2024). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 78.Li P., Guo C., Wang S., Ma D., Feng T., Wang Y., Qiu Y., Facile and general electrochemical deuteration of unactivated alkyl halides. Nat. Commun. 13, 3774 (2022). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 79.Guan W., Lu L., Jiang Q., Gittens A. F., Wang Y., Novaes L. F., Klausen R. S., Lin S., An electrochemical strategy to synthesize disilanes and oligosilanes from chlorosilanes. Angew. Chem. Int. Ed. Engl. 62, e202303592 (2023). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 80.Lu L., Siu J. C., Lai Y., Lin S., An electroreductive approach to radical silylation via the activation of strong Si–Cl bond. J. Am. Chem. Soc. 142, 21272–21278 (2020). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 81.Wang J., Li N., Ke J., He C., Recent advances in electrochemical silylation. Chin. J. Org. Chem. 44, 927–939 (2024). [Google Scholar]
  • 82.Jiao K.-J., Liu D., Ma H.-X., Qiu H., Fang P., Mei T.-S., Nickel-catalyzed electrochemical reductive relay cross-coupling of alkyl halides to aryl halides. Angew. Chem. Int. Ed. Engl. 59, 6520–6524 (2020). [DOI] [PubMed] [Google Scholar]
  • 83.Chen S., He X., Jing C., Zhang W., Yang Y., Liu S., Lan Y., Houk K. N., Shen X., Nickel-catalyzed cross-redistribution between hydrosilanes and silacyclobutanes. Angew. Chem. Int. Ed. Engl. 61, e202213431 (2022). [DOI] [PubMed] [Google Scholar]
  • 84.Reboli M., Kassamba S., Durandetti M., Nickel-catalyzed intramolecular hydrosilylation of alkynes: Embracing conventional and electrochemical routes. Chem. A Eur. J. 30, e202400440 (2024). [DOI] [PubMed] [Google Scholar]
  • 85.Zeng J., Chen J., Chen L., Zhan Z., Access to branched allylsilanes by nickel-catalyzed regioselective hydrosilylation of allenes. Org. Chem. Front. 7, 1132–1136 (2020). [Google Scholar]
  • 86.Zhang J., Guo J., Liu W., Liu M., Zhao D., Nickel(0)-catalyzed stereospecific and enantioselective ring-opening hydrosilylation of methylenecyclopropanes to access (E)-homoallylsilanes. ACS Catal. 15, 3126–3133 (2025). [Google Scholar]
  • 87.Qiu X., Zhou L., Wang H., Lu L., Ling Y., Zhang Y., Nickel(II)-catalyzed reductive silylation of alkenyl methyl ethers for the synthesis of alkyl silanes. RSC Adv. 11, 37083–37088 (2021). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 88.Hernandez D., Mose R., Skrydstrup T., Reductive lithiation of methyl substituted diarylmethylsilanes: Application to silanediol peptide precursors. Org. Lett. 13, 732–735 (2011). [DOI] [PubMed] [Google Scholar]
  • 89.Kuznetsov A., Gevorgyan V., General and practical one-pot synthesis of dihydrobenzosiloles from styrenes. Org. Lett. 14, 914–917 (2012). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 90.Liang H., Wang L.-J., Ji Y.-X., Wang H., Zhang B., Selective electrochemical hydrolysis of hydrosilanes to silanols via anodically generated silyl cations. Angew. Chem. Int. Ed. Engl. 60, 1839–1844 (2021). [DOI] [PubMed] [Google Scholar]
  • 91.Rodríguez A. M., Pérez-Ruíz J., Molina F., Poveda A., Pérez-Soto R., Maseras F., Pérez P. J., Introducing the catalytic amination of silanes via nitrene insertion. J. Am. Chem. Soc. 144, 10608–10614 (2022). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 92.Yang X., Wang C., Dichotomy of manganese catalysis via organometallic or radical mechanism: Stereodivergent hydrosilylation of alkynes. Angew. Chem. Int. Ed. Engl. 130, 935–940 (2018). [DOI] [PubMed] [Google Scholar]
  • 93.Parks D. J., Piers W. E., Tris(pentafluorophenyl)boron-catalyzed hydrosilation of aromatic aldehydes, ketones, and esters. J. Am. Chem. Soc. 118, 9440 (1996). [Google Scholar]
  • 94.Parks D. J., Blackwell J. M., Piers W. E., Studies on the mechanism of B(C6F5)3-catalyzed hydrosilation of carbonyl functions. J. Org. Chem. 65, 3090–3098 (2000). [DOI] [PubMed] [Google Scholar]
  • 95.Rubin M., Schwier T., Gevorgyan V., Highly efficient B(C6F5)3-catalyzed hydrosilylation of olefins. J. Org. Chem. 67, 1936–1940 (2002). [DOI] [PubMed] [Google Scholar]
  • 96.Wang W., Liu Y., Qiu G., Krylov I. B., Terent’ev A. O., Cao S., Sun K., Chen X., Qu L., Yu B., Photocatalytic germylation via direct hydrogen atom transfer. Chin. J. Chem. 43, 1664–1672 (2025). [Google Scholar]

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Supplementary Materials

Supplementary Text

Figs. S1 to S12

Tables S1 to S15

References

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Data Availability Statement

All data and code needed to evaluate and reproduce the results in the paper are present in the paper and/or the Supplementary Materials.

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