CN111732613A - Ferric iron complex containing meta-carborane ligand and preparation method and application thereof - Google Patents

Ferric iron complex containing meta-carborane ligand and preparation method and application thereof Download PDF

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CN111732613A
CN111732613A CN202010513570.6A CN202010513570A CN111732613A CN 111732613 A CN111732613 A CN 111732613A CN 202010513570 A CN202010513570 A CN 202010513570A CN 111732613 A CN111732613 A CN 111732613A
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关艾琳
姚子健
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Shanghai Institute of Technology
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    • C07F15/025—Iron compounds without a metal-carbon linkage
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    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
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Abstract

The invention relates to a ferric iron complex containing a meta-carborane triazole ligand, a preparation method and application thereof, wherein the ferric iron complex is prepared by the following steps: (1) dropwise adding the n-BuLi solution into the meta-carborane solution, stirring and reacting; then adding 3-bromopropyne for re-reaction, and separating to obtain 1, 3-dipropargyl m-carborane after the reaction is finished; (2) under the catalysis of CuI catalyst, 1, 3-dipropargyl meta-carborane reacts with aryl azide, and FeCl is added3Adding the mixture into a reaction system for continuous reaction, and separating to obtain the ligand containing the m-carboraneA trivalent iron complex of (1). The ferric iron complex is applied to catalyzing aldehyde, ortho-diketone and ammonium chloride to react in one pot under the solvent-free condition to synthesize the polysubstituted imidazole compound. Compared with the prior art, the ferric iron complex has simple preparation method, can be prepared with high yield, and can stably exist in the air.

Description

Ferric iron complex containing meta-carborane ligand and preparation method and application thereof
Technical Field
The invention relates to the field of complex synthesis, in particular to a ferric complex containing a meta-carborane ligand, and a preparation method and application thereof.
Background
The polysubstituted imidazole compounds are widely applied to synthesis of protein kinase inhibitors, calcium antagonists, cardiotonic agents, antitumor drugs and the like due to important physiological activities of the polysubstituted imidazole compounds. In addition, the compounds also have important application in the field of ionic liquid, such as good application prospect in the fields of organic synthesis, catalysis, extraction, mining and the like.
Wherein the synthesis of the 2,4, 5-trisubstituted imidazole is mainly prepared by the reaction of aldehyde, ortho-diketone and ammonium salt. Homogeneous catalysts such as ZrOCl are used for the reaction2·8H2O, heteropoly acid and (C)4H9)4Br、InCl3·3H2O、InF3Etc.; the heterogeneous supported catalyst has SiO2-TiCl4、Al2O3-NiCl2And supported FeCl3And the like. But many catalysts have the defects of complex preparation process, difficult obtainment of raw materials, higher cost and the like; catalytic reactions also typically require higher temperatures and the participation of organic solvents.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a ferric iron complex containing a meta-carborane ligand, which can efficiently catalyze multicomponent reactions of aldehyde, vicinal diketone and ammonium chloride to synthesize a 2,4, 5-trisubstituted imidazole compound by a one-pot method under the condition of room temperature and no solvent, and a preparation method and application thereof.
The purpose of the invention can be realized by the following technical scheme:
a ferric complex containing a meta carborane ligand, the ferric complex having the formula:
Figure BDA0002529313990000023
wherein R is H, OMe, NO2One of Cl or Br, "·" is a boron hydrogen bond.
A process for preparing a ferric complex containing a meta carborane triazole ligand as described above, comprising the steps of:
(1) preparation of 1, 3-dipropargyl meta-carborane: dropwise adding the n-BuLi solution into the meta-carborane solution, stirring and reacting; then adding 3-bromopropyne for re-reaction, and separating to obtain 1, 3-dipropargyl m-carborane after the reaction is finished; the reaction formula is as follows:
Figure BDA0002529313990000021
(2) preparation of a trivalent iron complex containing a meta-carborane ligand: under the catalysis of CuI catalyst, 1, 3-dipropargyl meta-carborane reacts with aryl azide, and FeCl is added3Adding the mixture into a reaction system for continuous reaction, and separating to obtain the ferric iron complex containing the meta-carborane ligand according to the reaction formula:
Figure BDA0002529313990000022
further, the molar ratio of the n-BuLi, the m-carborane and the 3-bromopropyne in the step (1) is (2.2-2.5) to 1.0 (2.2-2.5); CuI, 1, 3-dipropargyl meta-carborane, aryl azide and FeCl in step (2)3The molar ratio of (0.04-0.06) to (1.0), (1.2-1.5) to (0.8-1.2).
Further, the method is characterized in that the step (1) is specifically as follows:
(1-1) dropwise adding the n-BuLi solution into the m-carborane solution at a low temperature and stirring;
(1-2) heating to room temperature, and continuing to react;
(1-3) adding 3-bromopropyne for re-reaction, draining the solvent after the reaction is finished, and recrystallizing to obtain the 1, 3-dipropargyl m-carborane.
Further, the low temperature in the step (1-1) is-5 to 5 ℃; the n-BuLi solution is n-BuLi n-hexane solution, and the m-carborane solution is m-carborane ethyl ether solution; the stirring time is 25-35 min; the continuous reaction time in the step (1-2) is 30-60 min; and (3) carrying out the re-reaction for 2-4h, and carrying out recrystallization by adopting n-hexane.
Further, the step (2) is specifically as follows:
(2-1) dissolving 1, 3-dipropargyl meta-carborane and aryl azide in a solvent under the catalysis condition of a catalyst CuI, and reacting at room temperature;
(2-2) adding FeCl3Adding the mixture into a reaction system for continuous reaction, standing and filtering after the reaction is finished, decompressing and draining the solvent, and performing column chromatography separation on the obtained crude product to obtain the ferric iron complex containing the m-carborane triazole ligand.
Further, the solvent in the step (2-1) is tetrahydrofuran THF, the aryl azide comprises azidobenzene, 4-methoxy azidobenzene, 4-nitro azidobenzene, 4-chloro azidobenzene or 4-bromo azidobenzene, and the reaction time at room temperature is 3-6 h; the time for continuing the reaction in the step (2-2) is 3-6 h.
The ferric iron complex containing the meta-carborane triazole ligand is applied to catalyzing aldehyde, ortho-diketone and ammonium chloride to react in one pot to synthesize a polysubstituted imidazole compound under the solvent-free condition, and the synthesis process is simple and green and has excellent selectivity and high yield.
Further, the specific application method comprises the following steps: mixing aldehyde, ortho-diketone and ammonium chloride, reacting, and after the reaction is finished, carrying out silica gel column chromatography separation on concentrated reaction liquid to obtain the corresponding 2,4, 5-trisubstituted imidazole compound.
Further, the molar ratio of the ferric iron complex, the aromatic aldehyde, the ortho-diketone and the ammonium chloride is 0.005:1.0:1.0 (2.1-2.5), and the reaction time is 6-8 h; the aldehyde comprises one or more of benzaldehyde, 2-methyl benzaldehyde, 3-methyl benzaldehyde, 4-methoxy benzaldehyde, 4-chlorobenzaldehyde or 4-nitrobenzaldehyde; the vicinal diketone comprises one or two of butanedione or benzil.
The preparation method of the iron complex is simple and green. The iron complex can efficiently catalyze aldehyde, ortho-diketone and ammonium chloride to react in one pot to synthesize the polysubstituted imidazole compound under the solvent-free condition. The method has the advantages of mild reaction conditions, good universality, high catalytic efficiency, few byproducts, low cost, easy separation of products and no generation of a large amount of waste residues. And the iron complex is used as a catalyst, has high stability and is insensitive to air and water.
Compared with the prior art, the invention has the following characteristics:
(1) the preparation method of the trivalent iron complex containing the meta-carborane ligand is simple, can be used for preparing the complex with high yield, and can stably exist in the air;
(2) the iron complex can catalyze multicomponent reaction of aldehyde, vicinal diketone and ammonium chloride to synthesize the 2,4, 5-trisubstituted imidazole compound under the condition of no solvent at room temperature, the catalyst has low use equivalent weight, good selectivity, mild reaction conditions, high substrate universality and high yield, and high temperature and participation of an organic solvent are not needed.
Detailed Description
The following examples are given for the detailed implementation and specific operation of the present invention, but the scope of the present invention is not limited to the following examples.
Example 1: synthesis of ferric iron complex 1 and application thereof in preparation of 2,4, 5-trisubstituted imidazole compound
(1) n-BuLi (22.0mmol) in n-hexane was added dropwise to the m-C m-carborane at 0 deg.C2B10H12(10.0mmol) of ethyl ether solution, continuously stirring for 30 minutes after the dropwise addition is finished, slowly raising the temperature to room temperature, continuously reacting for 30 minutes, adding 3-bromopropyne (21.0mmol), continuously reacting for 3 hours at room temperature, draining the solvent after the reaction is finished, and recrystallizing the product by n-hexane to obtain the 1, 3-dipropargyl m-carborane C8B10H16(yield 85%) the reaction equation is:
Figure BDA0002529313990000041
1H NMR(400MHz,CDCl325 ℃ C.). about.3.55 (s, 2H.), 2.63(s, 4H.) theoretical value of elemental analysis C8B10H16: c43.61, H7.32; experimental values: c43.55, H7.30.
(2) CuI (0.05mmol), 1, 3-dipropargylpropyl m-carborane (1.0mmol) and azidobenzene (1.2mmol) are dissolved in T at room temperatureHF, at this temperature for 3 hours, and then FeCl3(1.0mmol) was added to the reaction system and reacted for an additional 6 hours. After the reaction is finished, standing and filtering, decompressing and draining the solvent, and performing column chromatography separation on the obtained crude product (dichloromethane/ethyl acetate ═ 5:1) to obtain a brown target product, namely, the ferric iron complex 1 (the yield is 77 percent), wherein the reaction equation is as follows:
Figure BDA0002529313990000051
1H NMR(400MHz,CDCl325 ℃ C.: 8.58(s,2H),7.75(d, J ═ 7.5Hz,4H),7.61(d, J ═ 7.5Hz,2H),7.49(t, J ═ 7.0Hz,4H),3.27(s,4H), theoretical value of elemental analysis C20B10H26Cl3N6Fe: c38.70, H4.22, N13.54; experimental values: c38.77, H4.21, N13.58.
(3) Mixing the ferric iron complex 1(0.005mmol), aromatic aldehyde (1.0mmol), ortho diketone (1.0mmol) and ammonium chloride (2.3mmol) in a reaction tube, reacting at room temperature for 7 hours, filtering after the reaction is finished, and separating and purifying a crude product through column chromatography, wherein the eluent is petroleum ether: and (4) obtaining the 2,4, 5-trisubstituted imidazole compound by taking dichloromethane as 6: 1. Specific results are shown in table 1.
TABLE 1
Figure BDA0002529313990000052
Figure BDA0002529313990000061
Example 2: synthesis of ferric iron complex 2
(1) Consistent with the synthetic method of example 1;
(2) CuI (0.05mmol), 1, 3-dipropargylpyrocarbylborane (1.0mmol) and 4-methoxyazidobenzene (1.5mmol) were dissolved in THF at room temperature, reacted at this temperature for 6 hours, and then FeCl was added3(1.0mmol) was added to the reaction system and reacted for an additional 6 hours. After the reaction is finished, standing and filtering, decompressing and pumping out the solvent, and carrying out column chromatography on the obtained crude productIsolation (dichloromethane/ethyl acetate ═ 3:1) afforded iron complex 2 (75% yield) as the target product in brown color according to the formula:
Figure BDA0002529313990000062
1H NMR(400MHz,CDCl325 ℃ C.: 8.44(s,2H),7.82(d, J ═ 7.5Hz,4H),7.53(d, J ═ 7.0Hz,4H),3.48(s,6H),3.19(s,4H), theoretical value of elemental analysis C22B10H30Cl3N6FeO2: c38.81, H4.44, N12.34; experimental values: c38.76, H4.48, N12.35.
Example 3: synthesis of ferric iron complex 3
(1) Consistent with the synthetic method of example 1;
(2) CuI (0.05mmol), 1, 3-dipropargylpyrocarbylborane (1.0mmol) and 4-nitroazidobenzene (1.3mmol) were dissolved in THF at room temperature, reacted at that temperature for 6 hours, and then FeCl was added3(1.0mmol) was added to the reaction system and reacted for another 8 hours. After the reaction is finished, standing and filtering, decompressing and draining the solvent, and performing column chromatography separation on the obtained crude product (dichloromethane/ethyl acetate ═ 5:1) to obtain a brown target product iron complex 3 (yield is 81 percent), wherein the reaction formula is as follows:
Figure BDA0002529313990000071
1H NMR(400MHz,CDCl325 ℃ C.: 8.33(s,2H),7.82(d, J ═ 7.2Hz,4H),7.75(d, J ═ 7.0Hz,4H),3.22(s,4H). theoretical value of elemental analysis C20B10H24Cl3N8FeO4: c33.80, H3.40, N15.77; experimental values: c33.89, H3.45, N15.75.
Example 4: synthesis of ferric iron complex 4
(1) Consistent with the synthetic method of example 1;
(2) CuI (0.05mmol), 1, 3-dipropargylpyrocarbylborane (1.0mmol) and 4-chloroazidobenzene (1.2mmol) were dissolved in THF at room temperature, reacted at that temperature for 3 hours, and thenFeCl is added3(1.0mmol) was added to the reaction system and reacted for an additional 7 hours. After the reaction is finished, standing and filtering, decompressing and draining the solvent, and performing column chromatography separation on the obtained crude product (dichloromethane/ethyl acetate is 3:1) to obtain a brown target product iron complex 4 (yield is 82%) which has the reaction formula:
Figure BDA0002529313990000072
1H NMR(400MHz,CDCl325 ℃ C.: 8.45(s,2H),7.80(d, J ═ 7.2Hz,4H),7.75(d, J ═ 7.2Hz,4H),3.27(s,4H). theoretical value of elemental analysis C20B10H24Cl5N6Fe: c34.83, H3.51, N12.19; experimental values: c34.78, H3.55, N12.28.
Example 5: synthesis of ferric iron complex 5
(1) Consistent with the synthetic method of example 1;
(2) CuI (0.05mmol), 1, 3-dipropargylpyrocarbylborane (1.0mmol) and 4-bromoazidobenzene (1.3mmol) were dissolved in THF at room temperature, reacted at that temperature for 6 hours, and then FeCl was added3(1.0mmol) was added to the reaction system and reacted for an additional 6 hours. After the reaction is finished, standing and filtering, decompressing and draining the solvent, and performing column chromatography separation on the obtained crude product (dichloromethane/ethyl acetate is 4:1) to obtain a brown target product iron complex 5 (yield is 85 percent), wherein the reaction formula is as follows:
Figure BDA0002529313990000081
1H NMR(400MHz,CDCl325 ℃ C.: 8.47(s,2H),7.82(d, J ═ 7.2Hz,4H),7.66(d, J ═ 7.2Hz,4H),3.26(s,4H). theoretical value of elemental analysis C20B10H24Cl3Br2N6Fe: c30.85, H3.11, N10.79; experimental values: c30.88, H3.17, N10.69.
The ferric iron complexes of examples 1-5 were used to catalyze the reaction of benzaldehyde, benzil and ammonium chloride with the iron complex as follows:
mixing a ferric iron complex (serving as a catalyst), benzaldehyde (1.0mmol), benzil (1.0mmol) and ammonium chloride in a reaction tube, reacting at room temperature for 6-8 hours, filtering after the reaction is finished, separating and purifying a crude product by column chromatography, wherein an eluent is petroleum ether: the 2,4, 5-trisubstituted imidazole compound is obtained by taking dichloromethane as 6:1, and the specific results are shown in table 1, and the reaction formula is as follows:
Figure BDA0002529313990000082
TABLE 2
Figure BDA0002529313990000083
Figure BDA0002529313990000091
Example 6
A ferric complex containing a meta carborane ligand, the ferric complex having the formula:
Figure BDA0002529313990000092
wherein, R is OMe, and the- (G-H) -is a boron hydrogen bond.
The preparation method of the iron complex comprises the following steps:
(1) adding n-BuLi n-hexane solution into m-carborane ether solution at-5 ℃, and then continuously stirring for 35 min; heating to room temperature, and continuing to react for 30 min; adding 3-bromopropyne, reacting at room temperature for 4h, draining the solvent after the reaction is finished, and recrystallizing by n-hexane to obtain 1, 3-dipropargyl m-carborane;
(2) dissolving 1, 3-dipropargyl meta-carborane, aryl azide and a catalyst CuI in an organic solvent tetrahydrofuran, and then reacting for 3 hours at room temperature; adding FeCl3Reacting at room temperature for 8h, standing and filtering after the reaction is finished, decompressing and pumping out the solvent to obtain a crude product, and then carrying out column chromatography separation on the crude product to obtain the compoundTo a ferric iron complex. Wherein, the catalyst, 1, 3-dipropargyl meta-carborane, aryl azide and FeCl3Is 0.05:1.0:1.2: 1.
The iron complex is used for catalyzing aromatic aldehyde, ortho-diketone and ammonium chloride to react and synthesize the 2,4, 5-trisubstituted imidazole compound by a one-pot method.
Example 7
A ferric complex containing a meta carborane ligand, the ferric complex having the formula:
Figure BDA0002529313990000101
wherein, R is OMe, and the- (G-H) -is a boron hydrogen bond.
The preparation method of the iron complex comprises the following steps:
(1) adding n-BuLi n-hexane solution into m-carborane ether solution at 5 ℃, and then continuously stirring for 25 min; heating to room temperature, and continuing to react for 60 min; adding 3-bromopropyne, reacting at room temperature for 2h, draining the solvent after the reaction is finished, and recrystallizing by n-hexane to obtain 1, 3-dipropargyl m-carborane;
(2) dissolving 1, 3-dipropargyl meta-carborane, aryl azide and a catalyst CuI in an organic solvent tetrahydrofuran, and then reacting for 6 hours at room temperature; adding FeCl3And reacting at room temperature for 6h, standing and filtering after the reaction is finished, decompressing and pumping out the solvent to obtain a crude product, and then carrying out column chromatography separation on the crude product to obtain the iron complex. Wherein, the catalyst, 1, 3-dipropargyl meta-carborane, aryl azide and FeCl3Is 0.05:1.0:1.5: 1.
The iron complex is used for catalyzing aromatic aldehyde, ortho-diketone and ammonium chloride to react and synthesize the 2,4, 5-trisubstituted imidazole compound by a one-pot method.
Example 8
A ferric complex containing a meta carborane ligand, the ferric complex having the formula:
Figure BDA0002529313990000111
wherein, R is OMe, and the- (G-H) -is a boron hydrogen bond.
The preparation method of the iron complex comprises the following steps:
(1) adding n-BuLi n-hexane solution into m-carborane ether solution at 0 ℃, and then continuously stirring for 30 min; heating to room temperature, and continuing to react for 45 min; adding 3-bromopropyne, reacting at room temperature for 3h, draining the solvent after the reaction is finished, and recrystallizing by n-hexane to obtain 1, 3-dipropargyl m-carborane;
(2) dissolving 1, 3-dipropargyl meta-carborane, aryl azide and a catalyst CuI in an organic solvent tetrahydrofuran, and then reacting for 4 hours at room temperature; adding FeCl3And reacting for 7 hours at room temperature, standing and filtering after the reaction is finished, decompressing and pumping out the solvent to obtain a crude product, and then carrying out column chromatography separation on the crude product to obtain the iron complex. Wherein, the catalyst, 1, 3-dipropargyl meta-carborane, aryl azide and FeCl3Is 0.05:1.0:1.3: 1.
The iron complex is used for catalyzing aromatic aldehyde, ortho-diketone and ammonium chloride to react and synthesize the 2,4, 5-trisubstituted imidazole compound by a one-pot method.
The embodiments described above are described to facilitate an understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.

Claims (10)

1. A ferric complex containing a meta carborane ligand, the ferric complex having the formula:
Figure FDA0002529313980000011
wherein R is H, OMe, NO2One of Cl or Br, "·" is a boron hydrogen bond.
2. A process for preparing a ferric complex with a meta carborane triazole ligand as claimed in claim 1, comprising the steps of:
(1) preparation of 1, 3-dipropargyl meta-carborane: dropwise adding the n-BuLi solution into the meta-carborane solution, stirring and reacting; then adding 3-bromopropyne for re-reaction, and separating to obtain 1, 3-dipropargyl m-carborane after the reaction is finished;
(2) preparation of a trivalent iron complex containing a meta-carborane ligand: under the catalysis of CuI catalyst, 1, 3-dipropargyl meta-carborane reacts with aryl azide, and FeCl is added3Adding the mixture into a reaction system for continuous reaction, and separating to obtain the ferric iron complex containing the meta-carborane ligand after the reaction is finished.
3. The method for preparing a trivalent iron complex containing a meta carborane triazole ligand according to claim 2, wherein the molar ratio of n-BuLi, meta carborane, and 3-bromopropyne in step (1) is (2.2-2.5):1.0 (2.2-2.5); CuI, 1, 3-dipropargyl meta-carborane, aryl azide and FeCl in step (2)3The molar ratio of (0.04-0.06) to (1.0), (1.2-1.5) to (0.8-1.2).
4. The preparation method of the trivalent iron complex containing the m-carborane triazole ligand as claimed in claim 2, wherein the step (1) is specifically as follows:
(1-1) dropwise adding the n-BuLi solution into the m-carborane solution at a low temperature and stirring;
(1-2) heating to room temperature, and continuing to react;
(1-3) adding 3-bromopropyne for re-reaction, draining the solvent after the reaction is finished, and recrystallizing to obtain the 1, 3-dipropargyl m-carborane.
5. The method for preparing a trivalent iron complex containing a m-carborane triazole ligand according to claim 4, wherein the low temperature in the step (1-1) is-5 to 5 ℃; the n-BuLi solution is n-BuLi n-hexane solution, and the m-carborane solution is m-carborane ethyl ether solution; the stirring time is 25-35 min; the continuous reaction time in the step (1-2) is 30-60 min; and (3) carrying out the re-reaction for 2-4h, and carrying out recrystallization by adopting n-hexane.
6. The preparation method of the trivalent iron complex containing the m-carborane triazole ligand as claimed in claim 2, wherein the step (2) is specifically as follows:
(2-1) dissolving 1, 3-dipropargyl meta-carborane and aryl azide in a solvent under the catalysis condition of a catalyst CuI, and reacting at room temperature;
(2-2) adding FeCl3Adding the mixture into a reaction system for continuous reaction, standing and filtering after the reaction is finished, decompressing and draining the solvent, and performing column chromatography separation on the obtained crude product to obtain the ferric iron complex containing the m-carborane triazole ligand.
7. The method for preparing the trivalent iron complex containing the m-carborane triazole ligand according to claim 6, wherein the solvent in the step (2-1) is Tetrahydrofuran (THF), the aryl azide comprises azidobenzene, 4-methoxy azidobenzene, 4-nitro-azidobenzene, 4-chloro-azidobenzene or 4-bromo-azidobenzene, and the room-temperature reaction time is 3-6 h; the time for continuing the reaction in the step (2-2) is 3-6 h.
8. The use of a ferric complex containing a meta-carborane triazole ligand according to claim 1, wherein the ferric complex is used to catalyze the one-pot reaction of aldehyde, vicinal diketone and ammonium chloride to synthesize a polysubstituted imidazole compound in the absence of a solvent.
9. The application of the trivalent iron complex containing the m-carborane triazole ligand as the claim 8, is characterized in that the specific application method comprises the following steps: mixing aldehyde, ortho-diketone and ammonium chloride, reacting, and after the reaction is finished, carrying out silica gel column chromatography separation on concentrated reaction liquid to obtain the corresponding 2,4, 5-trisubstituted imidazole compound.
10. The use of a trivalent iron complex containing a meta carborane triazole ligand as claimed in claim 8 or claim 9, wherein the molar ratio of the trivalent iron complex, the aromatic aldehyde, the ortho diketone and the ammonium chloride is 0.005:1.0:1.0 (2.1-2.5), and the reaction time is 6-8 h; the aldehyde comprises one or more of benzaldehyde, 2-methyl benzaldehyde, 3-methyl benzaldehyde, 4-methoxy benzaldehyde, 4-chlorobenzaldehyde or 4-nitrobenzaldehyde; the vicinal diketone comprises one or two of butanedione or benzil.
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CN110483581A (en) * 2019-08-09 2019-11-22 上海应用技术大学 It is a kind of containing the palladium complex of carborane ligand and its preparation and application between double phosphines
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CN110483581A (en) * 2019-08-09 2019-11-22 上海应用技术大学 It is a kind of containing the palladium complex of carborane ligand and its preparation and application between double phosphines
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