Monoboratriazole compound as well as synthesis method and application thereof

Abstract

The invention relates to a mono-boratriazole compound as well as a synthesis method and application thereof, positive ion boron-nitrogen alkyne and (trimethylsilyl) diazomethane are subjected to cycloaddition reaction, trimethylsilyl is migrated from carbon atoms to nitrogen atoms to form a positive ion mono-boratriazole framework, trimethylsilyl and counter ions are further removed by using alkali, and the mono-boratriazole compound is obtained. The mono-boratriazole compound is obtained. The mono-boratriazole compound disclosed by the invention has a wide application prospect in the fields of metal coordination reaction, reverse cyclization ring-opening reaction and preparation of unsaturated boron compounds.

Description

Technical Field

[0001] This invention belongs to the field of organic chemical synthesis technology, and relates to borotriazole compounds and their synthesis methods. Background Technology

[0002] Triazoles are an important class of aromatic heterocyclic compounds, classified structurally into 1,2,3-triazoles and 1,2,4-triazoles. They can act as organic ligands, coordinating with transition metals to form transition metal complexes or metal-organic frameworks. They also serve as important organic synthesis intermediates, widely used in the synthesis of a range of pesticides and pharmaceuticals. Their skeletal structure significantly influences the activity, stability, and bioavailability of drugs. Furthermore, triazoles are used to prepare various polymeric materials and nanomaterials, which exhibit excellent properties in optics, electronics, and magnetism, providing strong support for the development of modern science and technology.

[0003] The 1,2,3-triazole skeleton contains three consecutive nitrogen atoms. Its most efficient synthetic method involves the Huisgen cycloaddition reaction of an alkyne with an azide, a transformation that typically requires high temperatures. In 2002, Sharpless et al. reported a copper-catalyzed reaction of a terminal alkyne with an azide at room temperature, which can prepare 1,4-substituted 1,2,3-triazoles with high regioselectivity, hailed as a typical example of "click chemistry." The synthetic route is as follows:

[0004]

[0005] Introducing heteroatoms into the 1,2,3-triazole skeleton can effectively alter the polarity and electronic structure of the molecule, thereby obtaining modified functional molecules, which is of significant research importance from both basic research and practical application perspectives. Due to the rapid development of the diversity and wide application of boron-nitrogen heterocyclic compounds in recent years, the synthesis of boron triazole molecules and the study of their uses have become urgent priorities. Boron has one less electron than carbon; therefore, replacing the CH unit in triazole with an L→B unit can yield isoelectronic boron analogs of triazole. The introduction of boron atoms can effectively raise the HOMO orbital energy levels of the molecule, thereby improving the nucleophilicity and coordination ability of the molecule. Currently, only one case of the creation of a boron triazole structure has been reported. The Kinjo research group synthesized a diborane triazole compound for the first time under mild conditions via a cycloaddition reaction of diborene and azide. The synthetic route is as follows:

[0006]

[0007] Currently, there are no reports on neutral monoboranetriazole compounds, and their synthetic methods and properties are lacking. Therefore, this invention is proposed. Summary of the Invention

[0008] Given the lack of research on neutral monoboratriazole compounds and their synthetic routes in the prior art, this invention has conducted in-depth research in the field of monoboratriazole compounds. It was discovered that a positron borazine ion can undergo a 1,3-dipolar cycloaddition reaction with (trimethylsilyl)diazomethane. The reaction is accompanied by the migration of the trimethylsilyl group from carbon to nitrogen atoms, ultimately forming an ionic monoboratriazole ion. Further removal of the trimethylsilyl group and counterion using a base yields a neutral monoboratriazole compound. This invention is based on these findings.

[0009] Therefore, one object of the present invention is to provide a borate triazole compound, which is a neutral monoborazene triazole compound.

[0010] A second objective of this invention is to provide a method for synthesizing the above-mentioned monoboranetriazole compound.

[0011] A third object of the present invention is to provide the use of the above-mentioned monoboranetriazole compound.

[0012] The technical solution for achieving the above-mentioned objectives can be summarized as follows:

[0013] A monoborane triazole compound having the structure shown in Formula I:

[0014]

[0015] In Formula I, Ar is aryl; NHC is N-heterocyclic carbene.

[0016] According to the present invention, the preferred aryl group is 2,4,6-tri-tert-butylphenyl or terphenyl, with 2,4,6-tri-tert-butylphenyl being the most preferred; the N-heterocyclic carbene is a five-membered imidazole-derived carbene IPr2Me2, I with different substituents. t Bu and IMe4, with IPr2Me2 being the optimal choice; it has the following structure:

[0017]

[0018] According to the present invention, the method for synthesizing the above-mentioned monoborane triazole compound includes the following steps:

[0019] A cycloaddition reaction is carried out between a positively charged boronazine and (trimethylsilyl)diazomethane to give a positively charged monoboranetriazole. The trimethylsilyl group and counterion are removed by a base to give a neutral monoboranetriazole compound.

[0020] According to the present invention, preferably, the positive ion boronazine has the following structure:

[0021]

[0022] The (trimethylsilyl)diazomethane (TMSCHN2) described above has the following structure:

[0023]

[0024] The aforementioned positive ion monoboranetriazole has the following structure:

[0025]

[0026] According to the present invention, preferably, the alkali is an organic alkali, more preferably potassium bis(trimethylsilyl)amino (KHMDS), lithium bis(trimethylsilyl)amino (LiHMDS), or potassium tert-butoxide (KHMDS). t Among the various options, KHMDS is the preferred choice, including BuOK.

[0027] According to the present invention, preferably, the cycloaddition reaction between the positively charged boronazine and (trimethylsilyl)diazomethane is carried out in a solvent, preferably chloroform;

[0028] The reaction is carried out in an anhydrous and oxygen-free environment, preferably in a nitrogen atmosphere;

[0029] Preferably, the reaction is carried out at room temperature and pressure, with the preferred temperature being 20-30℃;

[0030] Further preferably, the molar ratio of positive ion boronazine to (trimethylsilyl)diazomethane is 1:(1-1.2), and most preferably 1:1.

[0031] According to the present invention, preferably, after the reaction is completed, a purification process is further included:

[0032] Preferably, after the reaction is complete, the solvent is removed, washed, extracted, recrystallized, and the solid-liquid separation is performed to obtain the positive ion monoboranetriazole.

[0033] According to the present invention, preferably, the reaction process of removing the trimethylsilyl group and counterion in the positive ion monoboranetriazole with base is carried out in a solvent, preferably tetrahydrofuran;

[0034] The reaction is carried out in an oxygen-free environment, preferably in a nitrogen atmosphere;

[0035] Preferably, the molar ratio of the positively charged monoboranetriazole to the organic base is 1:(1-1.2);

[0036] Preferably, the reaction is carried out at room temperature and pressure, with the preferred temperature being 20-30℃;

[0037] According to the present invention, preferably, after the reaction is completed, a purification process is further included:

[0038] Preferably, after the reaction is complete, the solvent is removed, followed by washing and extraction, and solid-liquid separation to obtain the target product, a neutral monoboranetriazole compound.

[0039] According to the present invention, the above-mentioned neutral monoboranetriazole compound is used in the following fields:

[0040] Used in metal coordination reactions;

[0041] Alternatively, it can be reacted with elemental sulfur to prepare B=S double-bonded compounds.

[0042] Alternatively, it can be used to prepare imine borane through a heated reverse cyclization ring-opening reaction.

[0043] The beneficial effects of this invention are:

[0044] This invention reports a novel monoboranetriazole compound and its synthetic method. The first synthesis of a neutral monoboranetriazole compound was achieved, and a synthetic method for monoboranetriazole compounds was provided, filling a gap in the existing research in this field. Through mild synthetic conditions and a simple purification process, monoboranetriazole compounds with unique electronic properties can be efficiently prepared. This compound, with its electron-rich framework, coordinateable nitrogen atoms, and easy breakage and recombination characteristics, shows practical applications in metal coordination reactions and the preparation of unsaturated boron compounds, providing new ideas and key breakthroughs for further research on its applications in catalysis, drug synthesis, materials science, and other fields. Attached Figure Description

[0045] Figure 1 The compound 1a obtained in Example 1 1 H NMR spectrum;

[0046] Figure 2 The compound 1a obtained in Example 1 13 C{ 1 H NMR spectrum;

[0047] Figure 3 The compound 1a obtained in Example 1 11 B NMR spectrum;

[0048] Figure 4 The X-ray single-crystal diffraction structure of compound 1a obtained in Example 1 is shown below.

[0049] Figure 5 Compound 2a obtained in Example 2 1 H NMR spectrum;

[0050] Figure 6 Compound 2a obtained in Example 2 13 C{ 1 H NMR spectrum;

[0051] Figure 7 Compound 2a obtained in Example 2 11 B NMR spectrum;

[0052] Figure 8 X-ray single-crystal diffraction structure of compound 2a obtained in Example 2;

[0053] Figure 9 Compound 3a was prepared in Example 3. 1 H NMR spectrum;

[0054] Figure 10 Compound 3a was prepared in Example 3. 13 C{ 1 H NMR spectrum;

[0055] Figure 11 Compound 3a was prepared in Example 3. 11 B NMR spectrum;

[0056] Figure 12 Compound 3a was prepared in Example 3. 27 Al NMR spectrum;

[0057] Figure 13 The X-ray single-crystal diffraction structure of compound 3a obtained in Example 3 is shown below.

[0058] Figure 14 X-ray single-crystal diffraction structure of compound 4a obtained in Example 4;

[0059] Figure 15 The image shows the X-ray single-crystal diffraction structure of compound 5a obtained in Example 5. Detailed Implementation

[0060] This invention involves a cycloaddition reaction between a positively charged boronazine and (trimethylsilyl)diazomethane, where the trimethylsilyl group migrates from the carbon atom to the nitrogen atom, forming an unprecedented positively charged monoboranetriazole skeleton. The trimethylsilyl group and counterion are then removed using a base to obtain the monoboranetriazole compound.

[0061] The monoborane triazole compound of the present invention has the structure shown in Formula I:

[0062]

[0063] In Formula I, Ar is aryl and NHC is N-heterocyclic carbene.

[0064] In one or more preferred embodiments, the aryl group is 2,4,6-tri-tert-butylphenyl or terphenyl; the N-heterocyclic carbene is a five-membered imidazole-derived carbene IPr2Me2, I with different substituents. t Bu and IMe4. They have the following structures:

[0065]

[0066] According to the present invention, the method for synthesizing the above-mentioned monoborane triazole compound includes the following steps:

[0067] A cycloaddition reaction is carried out between a positively charged boronazine and (trimethylsilyl)diazomethane to give a positively charged monoborazine. The trimethylsilyl group and counterion in the positively charged monoborazine are removed by a base to give a neutral monoborazine compound.

[0068] In one or more preferred embodiments, the positive ion boronazine has the following structure:

[0069]

[0070] The (trimethylsilyl)diazomethane (TMSCHN2) described above has the following structure:

[0071]

[0072] In one or more preferred embodiments, the positive ion monoboranetriazole has the following structure:

[0073]

[0074] In one or more preferred embodiments, the base is an organic base, more preferably potassium bis(trimethylsilyl)amino (KHMDS), lithium bis(trimethylsilyl)amino (LiHMDS), or potassium tert-butoxide (KHMDS). t Among the various options, KHMDS is the preferred choice, including BuOK.

[0075] In one or more preferred embodiments, the cycloaddition reaction of the positively charged boronazine with (trimethylsilyl)diazomethane is carried out in a solvent, preferably chloroform.

[0076] The reaction is carried out in an anhydrous and oxygen-free environment, preferably in a nitrogen atmosphere;

[0077] Preferably, the reaction is carried out at room temperature and pressure, with the preferred temperature being 20-30℃;

[0078] Further preferably, the molar ratio of positive ion boronazine to (trimethylsilyl)diazomethane is 1:(1-1.2), and most preferably 1:1.

[0079] According to the present invention, preferably, after the reaction is completed, a purification process is further included:

[0080] Preferably, after the reaction is complete, the solvent is removed, washed, extracted, recrystallized, and the solid-liquid separation is performed to obtain the positive ion monoboranetriazole.

[0081] In one or more preferred embodiments, the reaction of removing the trimethylsilyl group and counterion from the positive ion monoboranetriazole with a base is carried out in a solvent, preferably tetrahydrofuran;

[0082] The reaction is carried out in an oxygen-free environment, preferably in a nitrogen atmosphere;

[0083] Preferably, the molar ratio of the positively charged monoboranetriazole to the organic base is 1:(1-1.2);

[0084] Preferably, the reaction is carried out at room temperature and pressure, with the preferred temperature being 20-30℃.

[0085] In one or more preferred embodiments, after the reaction is complete, a purification process is further included:

[0086] Preferably, after the reaction is complete, the solvent is removed, followed by washing and extraction, and solid-liquid separation to obtain the target product, a neutral monoboranetriazole compound.

[0087] According to the present invention, the method for synthesizing the monoborane triazole compound includes the following steps:

[0088] Under a nitrogen atmosphere, compound 1 was dissolved in tetrahydrofuran, an organic base was added, and the mixture was stirred at room temperature for 1 hour. The solvent was then dried under vacuum, and the remaining solid was washed with hexane and extracted with toluene solution. After filtration, the filtrate was dried to obtain the target compound 2, which is a neutral monoborane triazole compound.

[0089] The preparation route is as follows:

[0090]

[0091] According to the present invention, the above-mentioned borate triazole compound is used in the following fields:

[0092] Used in metal coordination reactions;

[0093] Alternatively, it can be used to react with elemental sulfur in B=S double bond compounds;

[0094] Alternatively, it can be used to prepare imine borane through a heated reverse cyclization ring-opening reaction.

[0095] According to the present invention, the above application is further as follows:

[0096] Neutral monoboranetriazoles, with their multiple σ and π coordination sites, can achieve diverse metal coordination, making them unique ligands that play a crucial role in metal coordination reactions. In materials science, monoboranetriazoles can form stable coordination polymers with various metal ions, enabling the construction of functional metal-organic frameworks. These materials exhibit excellent performance in gas adsorption, separation, and fluorescent functional materials. Overall, monoboranetriazoles hold great potential for applications in drug development, materials science, and supramolecular chemistry, providing new ideas and methods for research and development in these fields.

[0097] Alternatively, it can react with elemental sulfur to prepare B=S double-bonded compounds. Heating monoborazine compounds in the presence of elemental sulfur yields borone intermediates, which can be oxidized in situ by elemental sulfur to form B=S double-bonded compounds. Due to their unique chemical properties, compounds with B=S double bonds can serve as synthetic intermediates for constructing complex organic molecules, particularly valuable in the synthesis of polycyclic structures and functionalized heterocycles. Furthermore, these compounds may exhibit excellent thermal stability and optical properties in materials science, making them suitable for developing novel functional materials. In medicinal chemistry, B=S double-bonded compounds can enhance the bioactivity of molecules by binding to enzyme active sites in vivo, thus possessing potential value in drug design and synthesis. Overall, the use of monoborazine in the preparation of B=S double-bonded compounds enriches the field of unsaturated boron chemistry.

[0098] Alternatively, it can be used to prepare imine boranes via a heated reverse cyclization ring-opening reaction. The application prospects of reverse cyclization ring-opening reactions of monoborane triazole compounds are mainly reflected in organic synthesis, materials science, and biomedicine. In organic synthesis, reverse cyclization ring-opening reactions can generate intermediates with unique structures, which can be used to construct complex organic molecules, such as polycyclic structures or functionalized heterocycles. In materials science, such reactions can be used to prepare high-performance, biodegradable cationic polymers, which show significant value in the biomedical field, for example, as gene carriers or drug delivery systems. Furthermore, by introducing responsive groups (such as disulfide bonds or orthogonal ester groups), these polymers can degrade under specific stimuli, thereby achieving efficient release of drugs or nucleic acids. Overall, the reverse cyclization ring-opening reaction of monoborane triazole compounds provides a new strategy for synthesizing complex molecules and developing high-performance materials, with broad application potential.

[0099] According to the present invention, the monoboron triazole compound 2 can react with AlMe3, GaCl3, [Rh(CO)2Cl... ]2The metal compounds Cr(CO)3(MeCN)3, Mo(CO)3(MeCN)3, and W(CO)3(MeCN)3 undergo coordination reactions. Preferably, the metal compound is AlMe3. The reaction route is as follows:

[0100]

[0101] Given the wide range of applications of triazoles in coordination chemistry, monoborane triazoles can also be used to construct metal-organic coordination polymers. These polymers exhibit excellent performance in catalysis, gas adsorption, and fluorescent probes. Furthermore, through coordination with metals, diverse structures can be synthesized, providing new research directions for materials science and asymmetric catalysis.

[0102] According to the present invention, the monoboranetriazole compound 2 reacts with elemental sulfur to undergo reverse cyclization and ring opening, releasing a borone intermediate, which is captured by elemental sulfur to yield a B=S double-bonded compound. The reaction route is as follows:

[0103]

[0104] The B=S double-bonded compounds formed by the reaction of monoboranetriazole with S8 possess unique chemical structures and potential applications. These compounds may serve as key intermediates in organic synthesis, leading to further transformations into complex organic molecules. Furthermore, B=S double-bonded compounds may enhance bioactivity by binding to enzyme active sites in vivo, thus holding potential applications in drug synthesis. In materials science, these compounds, due to their unique electronic structure and chemical stability, may also be used to develop novel functional materials. Overall, B=S double-bonded compounds demonstrate potential applications in organic synthesis, bioactive molecule synthesis, and materials science, but their specific applications still require further research and development.

[0105] According to the present invention, the monoboranetriazole compound 2 undergoes reverse cyclization ring-opening upon direct heating to 200°C, and the reaction route is as follows:

[0106]

[0107] The application of monoboranetriazole in the ring-opening reaction is mainly due to its versatility as a synthetic intermediate. The ring-opening reaction can generate highly reactive intermediates that can participate in various organic synthetic reactions, such as coupling reactions and cycloaddition reactions. Therefore, it has significant application prospects in organic synthesis, drug development, and materials science.

[0108] Taking (trimethylsilyl)aminopotassium as an example, the technical route of this invention is as follows:

[0109]

[0110] The present invention will be further described below through specific embodiments, but is not limited thereto.

[0111] Example 1: Preparation of compound 1a

[0112]

[0113] A cycloaddition reaction was carried out between the positive ion boronazine and (trimethylsilyl)diazomethane to give the positive ion monoborazinetriazole.

[0114] In a 50 mL Schlenk flask, 1 mmol (0.599 g) of ionic boronazine was added and dissolved in 15 mL of chloroform. A hexane solution of (trimethylsilyl)diazomethane (1 mmol, 0.5 mL, 2.0 M in hex) was slowly added dropwise while stirring at room temperature. The mixture was stirred for one hour. After the reaction was complete, the solvent was removed from the reaction mixture under negative pressure. The crude product was extracted with tetrahydrofuran solution, filtered, and the filtrate was concentrated until colorless crystals precipitated. The precipitated crystals were recrystallized overnight at -20 °C, and 0.644 g of the precipitated crystals were collected, yielding 90%. The product crystallized into colorless, blocky crystals in toluene solution at low temperature.

[0115] 1 H NMR (500MHz, CDCl3): δ = 7.48 (s, 2H, Ar-H), 6.97 (s, 1H, N = CH), 4.74 (br, 2H, CH (CH3) 2) ,2.30(s,6H,CH3),1.25(s,21H,CH3),0.94(s,18H,C(CH3)3),0.58(s,9H,Si(CH3)3);

[0116] 13 C{ 1 H}NMR (126MHz, CDCl3): δ = 151.2 (C q ),146.1(C q ),134.6(C q ),129.6(C q ),125.0(CH),53.1(CH(CH3)2),37.9(C q ),35.2(C q ),32.3(CH3),31.4(CH3),21.4(CH3),11.3(CH3),–0.6(CH3),BC was not observed;

[0117] 11B NMR (160 MHz, CDCl3): δ = 22.6 (br);

[0118] Example 2, Preparation of compound 2a

[0119]

[0120] The trimethylsilyl group and counterion in the positive ion monoboranetriazole were removed by KHMDS to obtain neutral monoboranetriazole.

[0121] In a 50 mL Schlenk flask, the positively charged monoboranetriazole 1a (1 mmol, 0.714 g) prepared in Example 1 was added and dissolved in 15 mL of tetrahydrofuran. KHMDS (1 mmol, 0.199 g) was dissolved in 10 mL of tetrahydrofuran. The tetrahydrofuran solution of KHMDS was slowly added dropwise to compound 1a at room temperature with stirring. After the addition was complete, the mixture was stirred for one hour. After the reaction was complete, the solvent was removed from the reaction mixture under negative pressure. The crude product was washed with n-hexane and then extracted with toluene solution. The product was dried to obtain 0.354 g of a pale yellow solid powder, with a yield of 72%. The product crystallized into colorless blocky crystals in toluene solution at low temperature.

[0122] 1 H NMR (500MHz, C6D6): δ=7.62(s,2H,Ar-H),7.55(s,1H,BCH),5.39(s,2H,CH(CH3)2),1.63(s ,6H,CH3),1.38(s,9H,C(CH3)3),1.31(s,18H,C(CH3)3),0.86(d,J=5.8Hz,12H,CH(CH3)2).

[0123] 13 C{ 1 H}NMR (126MHz, C6D6): δ = 147.7 (C q ),147.6(C q ),141.05(BNC),128.35(BCH),126.63(NCCH3),123.88(Ar-CH),51.85(CH(CH3)2),38.31(C(CH3 )3),34.98(C(CH3)3),33.00(C(CH3)3),31.73(C(CH3)3),20.97(CH(CH3)2),10.08(NCCH3),NCN was not observed.

[0124] 11B NMR (160MHz, C6D6): δ = 20.52 (br).

[0125] Example 3: Preparation of compound 3a

[0126]

[0127] In a 25 mL Schlenk tube, add 0.5 mmol (0.246 g) of monoboranetriazole 2a prepared in Example 2, dissolve it in a small amount of benzene (5 mL), then add a toluene solution of trimethylaluminum (0.5 mmol, 0.25 mL, 2.0 M in tol), shake for five minutes, filter immediately, and allow the filtrate to stand at room temperature to evaporate and precipitate colorless flaky crystals. Collect 0.268 g of the product, with a yield of 95%.

[0128] 1 H NMR (500MHz, C6D6): δ = 7.36 (s, 2H, Ar-H), 6.91 (s, 1H, BCH), 5.01 (s, 2H, CH (CH3) 2), 2.19 (s, 6H, CH3 ),1.19(s,9H,C(CH3)3),1.12(s,12H,CH(CH3)2),0.92(s,18H,C(CH3)3),-0.88(s,9H,Al(CH3)2).

[0129] 13 C{ 1 H}NMR (126MHz, C6D6): δ = 149.36 (C q ),146.65(C q ),137.19(BNC),127.68(NCCH3),124.42(Ar-CH),52.45(CH3),37.91(C(CH3)3),35.00(C(CH3)3) ,32.39(C(CH3)3),31.50(C(CH3)3),21.21(CH(CH3)2),10.79(CH(CH3)2),-8.19(Al(CH3)3).BCH and NCN was not observed.

[0130] 11 B NMR (160MHz, C6D6): δ = 20.83 (br).

[0131] 27 Al NMR (130MHz, C6D6): δ = 72.96 (br).

[0132] Example 4, Preparation of compound 4a

[0133]

[0134] In a 50 mL reaction tube, add 0.5 mmol, 0.246 g of monoborazine 2a prepared in Example 2, dissolve it in a small amount of benzene (5 mL), then add excess S8 (0.3 mmol, 0.0768 g), heat at 60 °C for 2 hours, filter, and the filtrate evaporates at room temperature to obtain pale yellow blocky crystals.

[0135] Example 5: Preparation of compound 5a

[0136]

[0137] In a J-Young tube, 0.3 mmol, 0.148 g of monoboranetriazole 2a solid prepared in Example 2 was added and heated to 200 °C until the pale yellow solid turned into a yellow oily compound. The product was then extracted with n-hexane solution and the product crystallized into yellow blocky crystals in n-hexane solution at low temperature.

Claims

1. A monoboranetriazole compound, characterized in that, This borotriazole compound has the structure shown in Formula I: In Formula I, Mes* represents aryl, and NHC represents N-heterocyclic carbene.

2. The monoboranetriazole compound according to claim 1, characterized in that, The aryl group is 2,4,6-tri-tert-butylphenyl or terphenyl; the N-heterocyclic carbene is a five-membered imidazole-derived carbene IPr2Me2, I with different substituents. t Bu and IMe4 have the following structures:

3. A method for synthesizing the borate triazole compound according to claim 1 or 2, comprising the following steps: A cycloaddition reaction is carried out between a positively charged boronazine and (trimethylsilyl)diazomethane to give a positively charged monoborazine. The trimethylsilyl group and counterion in the positively charged monoborazine are removed by a base to give a neutral monoborazine compound.

4. The method for synthesizing monoboranetriazole compounds according to claim 3, characterized in that, The positive ion boronazine has the following structure: The (trimethylsilyl)diazomethane (TMSCHN2) described above has the following structure: The aforementioned positive ion monoboranetriazole has the following structure:

5. The method for synthesizing monoborane triazole compounds according to claim 3, characterized in that, The alkali is an organic alkali, preferably potassium bis(trimethylsilyl)amino, lithium bis(trimethylsilyl)amino, or potassium tert-butoxide.

6. The method for synthesizing monoboranetriazole compounds according to claim 3, characterized in that, The cycloaddition reaction between the positively charged boronazine and (trimethylsilyl)diazomethane is carried out in a solvent; the preferred solvent is chloroform. Preferably, the reaction is carried out in an anhydrous and oxygen-free environment, and more preferably in a nitrogen atmosphere; Preferably, the reaction is carried out at room temperature and pressure, with the preferred temperature being 20-30℃; Preferably, the molar ratio of positive ion boronazine to (trimethylsilyl)diazomethane is 1:(1-1.2).

7. The method for synthesizing monoborane triazole compounds according to claim 3, characterized in that, After the cycloaddition reaction of the positively charged boronazine with (trimethylsilyl)diazomethane is completed, the process also includes a purification process: Preferably, after the reaction is complete, the solvent is removed, washed, extracted, recrystallized, and the solid-liquid separation is performed to obtain the positive ion monoboranetriazole.

8. The method for synthesizing monoborane triazole compounds according to claim 3, characterized in that, The reaction of removing the trimethylsilyl group and counterion from the positive ion monoboranetriazole with a base is carried out in a solvent, preferably tetrahydrofuran. Preferably, the reaction is carried out in an anaerobic environment, and more preferably in a nitrogen atmosphere; Preferably, the molar ratio of the positively charged monoboranetriazole to the organic base is 1:(1-1.2); Preferably, the reaction is carried out at room temperature and pressure, with the preferred temperature being 20-30℃.

9. The method for synthesizing monoborane triazole compounds according to claim 3, characterized in that, After the reaction of removing the trimethylsilyl group and counterion from the positively charged monoboranetriazole with alkali is completed, the purification process is also included: Preferably, after the reaction is complete, the solvent is removed, followed by washing and extraction, and solid-liquid separation to obtain the target product, a neutral monoboranetriazole compound.

10. The use of the monoboranetriazole compound according to claim 1 or 2 in the following fields: Used in metal coordination reactions; Alternatively, it can be used to react with elemental sulfur in B=S double bond compounds; Alternatively, it can be used to prepare imine borane through a heated reverse cyclization ring-opening reaction.

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