A method for preparing a diaryl sulfide compound

Abstract

The application discloses a preparation method of a diaryl sulfide compound and belongs to the technical field of organic synthesis. The method uses cheap and easily obtained diaryl disulfide as a single raw material, and a desulfurization reaction occurs in a nickel or palladium catalyst, a phosphine ligand, a metal reducing agent, an organic base and an organic solvent, so that corresponding diaryl sulfide is obtained after purification treatment. The method has the advantages of cheap and easily obtained raw material, no use of halogen-containing compounds and pre-functionalized coupling reagents, low catalyst amount, high yield, convenient operation and the like, and has a high industrial application prospect.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic synthesis, and more particularly to a preparation method of diaryl sulfide compounds. BACKGROUND

[0002] Diaryl sulfide compounds have a wide range of applications in the fields of biological medicine, pesticides, dye intermediates, and organic polymer functional materials. There are mainly the following methods for synthesizing diphenyl sulfide: 1) diphenyl sulfide is prepared by reacting benzene and sulfur chloride under the catalysis of aluminum chloride, in which process a large amount of waste is generated, such as hydrogen chloride, hydrogen sulfide waste gas, and aluminum chloride complex solid waste, which causes serious pollution and energy consumption (Org. Synth. 1934, 14, 36); 2) diphenyl sulfide can also be prepared by reacting benzene / chlorobenzene and sulfur; 3) transition metal-catalyzed coupling reaction to synthesize diaryl sulfide, which specifically includes the coupling reaction of coupling reagents such as aryl halogen ArX (X = Cl, Br, I), aryl amine ArNR2, aryl phenol derivative ArOR, aryl borane ArB(OH)2, aryl metal (ArZnX, ArMgBr), aryl silicon ArSi(OEt)3, and sulfur-containing coupling reagents such as aryl thiol ArSH, aryl sodium sulfide ArSNa, and diaryl disulfide ArSSAr under the catalysis of transition metals (Pd, Ni, Cu, etc.) to prepare diaryl sulfide ArSAr (Mini-Reviews in Organic Chemistry, 2017, 14, 407-431);

[0003]

[0004] The above synthesis methods all use a variety of starting materials and pre-functionalization reagents to prepare aryl sulfide. Recently, a method for synthesizing diaryl sulfide by copper-catalyzed desulfurization of diaryl disulfide has been reported (ACS Catal. 2020, 10, 2707-2712), in which the consumption of copper catalyst (20 mol% dosage) and ligand (40 mol% dosage) is large, and the S atom is removed in the form of SO2, which has a large environmental pollution risk.

[0005] SUMMARY

[0006] The present application aims to provide a method for efficiently desulfurizing and preparing diaryl sulfide compounds Ar 1 SSAr 2 The present application aims to provide a method for efficiently desulfurizing and preparing diaryl sulfide compounds Ar 1 SAr 2 The present application aims to provide a method for efficiently desulfurizing and preparing diaryl sulfide compounds Ar 1 SSAr 1 The present application aims to provide a method for efficiently desulfurizing and preparing diaryl sulfide compounds Ar 1The SH oxidative dehydrogenation can be prepared, the substrate is widely applicable, the operation is convenient, the catalyst usage is low, the reaction yield is high, the cost is low, and the pollution is small.

[0007] To solve the problems raised in the above background art.

[0008] To achieve the above object, the present application provides the following technical scheme:

[0009] A preparation method of a diaryl sulfide compound, comprising the following steps:

[0010] S1: In an anhydrous and oxygen-free environment, such as a glove box, a diaryl disulfide, a catalyst, and a ligand having a structure as shown in formula (I) are added into a reactor, such as a Schlenk reaction tube, under an inert gas or nitrogen atmosphere;

[0011] S2: Base, metal, and organic solvent are further added into S1; under a certain temperature in a sealed environment, reaction is carried out, and after column chromatography separation and purification treatment, a diaryl sulfide compound having a structure as shown in formula (II) is obtained;

[0012]

[0013] Formula (I);

[0014]

[0015] Formula (II);

[0016] Wherein, Ar 1 and Ar 2 are independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted heterocyclic aromatic group containing N, O, and S atoms; Ar 1 and Ar 2 are the same or different;

[0017] On the phenyl, naphthyl, and heterocyclic aromatic group containing N, O, and S atoms, the substituted groups include one or more substituted C6-C 20 long chain alkyl groups in ortho, meta, and para positions, or one or more substituted C6-C 20 branched alkyl groups in ortho, meta, and para positions, or one or more substituted C6-C 20 long chain alkoxy groups in ortho, meta, and para positions, or one or more substituted C6-C 20 branched alkoxy groups in ortho, meta, and para positions, or one or more of chlorine, aliphatic group, aldehyde group, trifluoromethyl group, cyano group, amino group, and phenyl group; further, the substituent groups of the aromatic ring are one or more of methyl group, methoxy group, chlorine, and phenyl group in ortho, meta, and para positions.

[0018] Preferably, the reaction structure of the diaryl disulfide to diaryl sulfide compound is shown as formula (III):

[0019]

[0020] Formula (III).

[0021] Preferably, the metal reducing agent is one or more of Zn, Mg, Cu, Fe and Al, preferably Zn.

[0022] Preferably, the reaction temperature is 50-150°C, and the reaction time is 4-24h.

[0023] Preferably, the catalyst is selected from any one or a mixture of two of nickel, palladium, platinum and rhodium catalysts;

[0024] Preferably, the nickel catalyst is any one or more of bis-triphenylphosphine nickel dichloride Ni(Ph3P)2Cl2, (1,1'-bis(diphenylphosphino)ferrocene)nickel dichloride Ni(dppf)Cl2, 1,3-bis(diphenylphosphino)propane nickel dichloride Ni(dppp)Cl2, bis-(1,5-cyclooctadiene)nickel Ni(cod)2, tetrakis(triphenylphosphine)nickel Ni(Ph3P)4, nickel chloride NiCl2and nickel bromide NiBr2; further, the nickel catalyst is any one or both of bis-triphenylphosphine nickel dichloride Ni(Ph3P)2Cl2and tetrakis(triphenylphosphine)nickel Ni(Ph3P)4.

[0025] Preferably, the palladium catalyst is any one or more of tris(dibenzylideneacetone)dipalladium Pd2(dba)3, (dibenzylideneacetone)palladium Pd(dba)2, tetrakis(triphenylphosphine)palladium Pd(Ph3P)4, palladium acetate Pd(OAc)2, palladium chloride PdCl2, palladium bromide PdBr2, 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride Pd(dppf)Cl2, 1,4-bis(diphenylphosphino)butane palladium dichloride Pd(dppb)Cl2and bis-triphenylphosphine palladium dichloride Pd(Ph3P)2Cl2; further, the palladium catalyst is any one or more of tris(dibenzylideneacetone)dipalladium Pd2(dba)3, tetrakis(triphenylphosphine)palladium Pd(Ph3P)4and bis-triphenylphosphine palladium dichloride Pd(Ph3P)2Cl2.

[0026] Preferably, the platinum catalyst is one or both of platinum chloride PtCl2and tetrakis(triphenylphosphine)platinum Pt(Ph3P)4.

[0027] Preferably, the rhodium catalyst is one or more of tris(triphenylphosphine)rhodium chloride Rh(PPh3)3Cl, tetracarbonyl dichlorodirhodium Rh2(CO)4Cl2 and tris(dibenzylideneacetone)rhodium Rh(dba)3.

[0028] Preferably, the molar ratio of the metal catalyst to the diaryl disulfide is 0.1% to 20%.

[0029] Preferably, the ligand comprises one or more of a tridentate ligand, a bidentate phosphine ligand and a monodentate phosphine ligand.

[0030] Preferably, the monodentate phosphine ligand comprises one or more of triphenylphosphine (Ph3P), tricyclohexylphosphine (Cy3P), diphenylmethylphosphine (MePPh2) and phenyldimethylphosphine (Me2PPh); the bidentate phosphine ligand comprises one or more of bis-diphenylphosphinomethane (dppm), bis-diphenylphosphineethane (dppe), bis-diphenylphosphinopropane (dppp), bis-diphenylphosphinobutane (dppb), bis-diphenylphosphinohexane (dpph), 1,1'-bis(diphenylphosphino)ferrocene (dppf), the bidentate phosphine ligand comprises one or more of 1,1'-binaphthalene-2,2'-bis(diphenylphosphine) (BINAP) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos); further, the bidentate phosphine ligand comprises one or more of bis-diphenylphosphinomethane (dppm), bis-diphenylphosphineethane (dppe), bis-diphenylphosphinopropane (dppp), bis-diphenylphosphinobutane (dppb), bis-diphenylphosphinohexane (dpph) and 1,1'-bis(diphenylphosphino)ferrocene (dppf).

[0031] The ligand can adjust the electrical property of the catalyst metal center, thereby changing its catalytic activity, and also adjust the reaction course of the oxidative addition and reductive elimination, etc.; or no ligand is added, and the yield is slightly lower than that with the ligand.

[0032] Preferably, the base is an organic base, and the organic base is selected from one or more combinations of lithium tert-butoxide, lithium methoxide, lithium ethoxide, lithium hexamethyldisilylamide, lithium diisopropylamide, potassium tert-butoxide, sodium tert-butoxide, sodium carbonate, potassium carbonate, lithium carbonate, sodium methoxide and sodium ethoxide; further, the organic base is selected from one or more combinations of lithium tert-butoxide, lithium methoxide, lithium ethoxide, potassium tert-butoxide, sodium tert-butoxide, sodium methoxide and sodium ethoxide; or one of other common organic bases.

[0033] Preferably, the organic solvent is selected from one or any mixture of tetrahydrofuran, acetonitrile and DMF.

[0034] Compared with the prior art, the present application has the following beneficial effects:

[0035] The synthesis method of the diaryl disulfide provided by the application opens up a new synthesis catalytic system and a synthesis path of aryl sulfide; the defects of preparation by various starting materials are overcome; the diaryl sulfide compound can be obtained by using a single starting material; the single starting material is simple to obtain and can be prepared by oxidation and dehydrogenation of aryl sulfur ArSH; no halogen-containing compound and pre-functionalized coupling reagent is used, the yield of the target product is high, the reaction condition is mild, the operation is simple, the cost is low, no pollution gas is generated, and the method has high industrial application prospect. BRIEF DESCRIPTION OF DRAWINGS

[0036] Figure 1 The application provides a preparation method specific reaction structure process diagram;

[0037] Figure 2 The application provides a diaryl disulfide schematic diagram;

[0038] Figure 3 The application provides a diaryl sulfide compound schematic diagram. DETAILED DESCRIPTION

[0039] Example 1:

[0040] The application provides a technical solution:

[0041] Through the dose amplification reaction experiment, the influence of the dose of different materials on the reaction result under the same reaction condition and reaction material is detected:

[0042] When the dose is 1.0 mmol:

[0043] Under the protection of nitrogen, diphenyl disulfide (1.0 mmol), Pd2(dba)3 (0.01 mmol), dppb (0.02 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2.0 mL) are sequentially added into a 25 mL Schlenk reaction tube, mixed and stirred, then reacted at 70 DEG C for 4 hours, after the reaction is completed, the target product diphenyl sulfide is separated by column chromatography, is a colorless liquid, and the yield is 86%.

[0044] When the dose is 10 mmol:

[0045] Under the protection of nitrogen, diphenyl disulfide (10.0 mmol), Pd2(dba)3 (0.1 mmol), dppb (0.2 mmol), lithium tert-butoxide (20.0 mmol), zinc powder (20.0 mmol) and tetrahydrofuran (20 mL) are sequentially added into a 250 mL Schlenk reaction tube, mixed and stirred, then reacted at 70 DEG C for 12 hours, after the reaction is completed, the target product diphenyl sulfide is separated by column chromatography, is a colorless liquid, and the yield is 87%.

[0046] From the above experiment, under the same material and experimental conditions, the diphenyl sulfide extracted from the diphenyl disulfide compound is a colorless liquid, and the yield is 86% and 87% respectively. With the increase of the dose, the yield is increased by 1%. The dose has little effect on the preparation method of the present application. Therefore, the preparation method of the present application has the prospect of large-scale production, and the yield will not decrease.

[0047] Example 2:

[0048] Ar 1 = Ar 2 , and the yield is different. The substituent group in each experiment is selected under the condition of the highest yield.

[0049] Experiment 1:

[0050] Under the protection of nitrogen, 4,4'-dimethyl diphenyl disulfide (1.0 mmol), Pd2(dba)3(0.02 mmol), dppb (0.04 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2.0 mL) were added into a 25 mL Schlenk reaction tube in sequence. After mixing and stirring, the reaction was carried out at 90°C for 24 hours. After the reaction was completed, the target product 4,4'-dimethyl diphenyl sulfide was separated by column chromatography, which was a white solid with a yield of 97%.

[0051] Experiment 2:

[0052] Under the protection of nitrogen, 3,3'-dimethyl diphenyl disulfide (1.0 mmol), Pd2(dba)3(0.02 mmol), dppb (0.04 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2.0 mL) were added into a 25 mL Schlenk reaction tube in sequence. After mixing and stirring, the reaction was carried out at 90°C for 24 hours. After the reaction was completed, the target product 3,3'-dimethyl diphenyl sulfide was separated by column chromatography, which was a colorless liquid with a yield of 86%.

[0053] Experiment 3:

[0054] Under nitrogen protection, 2,2'-dimethyl diphenyl disulfide (1.0 mmol), Pd2(dba)3(0.02 mmol), dppb (0.04 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2 mL) were added into a 25 mL Schlenk tube in turn. After mixing and stirring, the mixture was reacted at 90 °C for 24 hours. After the reaction was completed, the target product 2,2'-dimethyl diphenyl sulfide was obtained by column chromatography, white solid, with a yield of 95%.

[0055] Experiment 4:

[0056] Under nitrogen protection, 4,4'-dimethoxy diphenyl disulfide (1.0 mmol), Pd2(dba)3(0.02 mmol), dppb (0.04 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2 mL) were added into a 25 mL Schlenk tube in turn. After mixing and stirring, the mixture was reacted at 90 °C for 24 hours. After the reaction was completed, the target product 4,4'-dimethoxy diphenyl sulfide was obtained by column chromatography, white solid, with a yield of 97%.

[0057] Experiment 5:

[0058] Under nitrogen protection, 4,4'-dichloro diphenyl disulfide (1.0 mmol), Pd2(dba)3(0.01 mmol), dppb (0.02 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2 mL) were added into a 25 mL Schlenk tube in turn. After mixing and stirring, the mixture was reacted at 90 °C for 22 hours. After the reaction was completed, the target product 4,4'-dichloro diphenyl sulfide was obtained by column chromatography, colorless liquid, with a yield of 88%.

[0059] Experiment 6:

[0060] Under nitrogen protection, 2-naphthalene disulfide (1.0 mmol), Pd2(dba)3(0.02 mmol), dppb (0.04 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2 mL) were added into a 25 mL Schlenk tube in turn. After mixing and stirring, the mixture was reacted at 90 °C for 21 hours. After the reaction was completed, the target product 2-naphthalene sulfide was obtained by column chromatography, white solid, with a yield of 89%.

[0061] Experiment 7:

[0062] Under nitrogen protection, 2-thiophene disulfide (1.0 mmol), Pd2(dba)3(0.04 mmol), dppb (0.08 mmol), lithium tert-butoxide (2.2 mmol), zinc powder (2.2 mmol) and tetrahydrofuran (2 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the reaction was carried out at 90°C for 4 hours. After the reaction was completed, the target product 2-thiophene sulfide was separated by column chromatography, which was a colorless liquid with a yield of 50%.

[0063] Experiment 8:

[0064] Under nitrogen protection, 2-thiophene disulfide (1.0 mmol), Pd2(dba)3(0.04 mmol), dppb (0.08 mmol), lithium tert-butoxide (2.2 mmol), zinc powder (2.2 mmol) and tetrahydrofuran (2 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the reaction was carried out at 90°C for 4 hours. After the reaction was completed, the target product 2-thiophene sulfide was separated by column chromatography, which was a colorless liquid with a yield of 50%.

[0065] Experiment 9:

[0066] Under nitrogen protection, 2-thiophene disulfide (1.0 mmol), Pd2(dba)3(0.04 mmol), dppb (0.08 mmol), lithium tert-butoxide (2.2 mmol), zinc powder (2.2 mmol) and tetrahydrofuran (2 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the reaction was carried out at 90°C for 4 hours. After the reaction was completed, the target product 2-thiophene sulfide was separated by column chromatography, which was a colorless liquid with a yield of 50%.

[0067] Experiment 10:

[0068] Under nitrogen protection, 2-thiophene disulfide (1.0 mmol), Pd2(dba)3(0.04 mmol), dppb (0.08 mmol), lithium tert-butoxide (2.2 mmol), zinc powder (2.2 mmol) and tetrahydrofuran (2 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the reaction was carried out at 90°C for 4 hours. After the reaction was completed, the target product 2-thiophene sulfide was separated by column chromatography, which was a colorless liquid with a yield of 50%.

[0069] In experiments 9 and 10, diphenyl diselenide and diphenyl ditelluride were added. Since sulfur, selenium and tellurium are in the same main group, their properties and reactions are similar, so the desulfurization strategy is applied to the preparation of diselenide and ditelluride.

[0070] Example 2-1:

[0071] In the same conditions as in experiment 1 of example 1, the organic base lithium tert-butoxide was replaced by lithium hexamethyldisilazide, with a yield of 38%.

[0072] Example 2-2:

[0073] In the same conditions as in experiment 1 of example 1, the bidentate phosphorus ligand dppb was replaced by 1,1'-binaphthalene-2,2'-diphenylphosphine (BINAP), with a yield of 64%.

[0074] Example 2-3:

[0075] In the same conditions as in experiment 1 of example 1, the bidentate phosphorus ligand dppb was replaced by triphenylphosphine (Ph3P), with a yield of 56%.

[0076] Example 2-4:

[0077] In the same conditions as in experiment 1 of example 1, the bidentate phosphorus ligand dppb was replaced by tricyclohexylphosphine (Cy3P), with a yield of 44%.

[0078] Example 2-5:

[0079] In the same conditions as in experiment 1 of example 1, the organic solvent tetrahydrofuran was replaced by acetonitrile, with a yield of 76%.

[0080] Example 2-6:

[0081] In the same conditions as in experiment 1 of example 1, the organic solvent tetrahydrofuran was replaced by DMF, with a yield of 56%.

[0082] Example 2-7:

[0083] In the same conditions as in experiment 1 of example 1, Pd2(dba)3(0.02 mmol) was replaced by PdCl2(0.04 mmol), with a yield of 82%.

[0084] Example 2-8:

[0085] In the same conditions as in experiment 1 of example 1, Pd2(dba)3(0.02 mmol) was replaced by Pd(OAc)2(0.04 mmol), with a yield of 65%.

[0086] Example 3:

[0087] Ar 1 ≠ Ar 2 , and of different species:

[0088] Experiment 1:

[0089] Under nitrogen protection, 1-phenyl-2-(4-methylphenyl) disulfide (1.0 mmol), Pd2(dba)3(0.02 mmol), dppb (0.04 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the mixture was reacted at 90°C for 20 hours. After the reaction was completed, the target product 1-phenyl-2-(4-methylphenyl) sulfide was separated by column chromatography, and was a colorless liquid with a yield of 82%.

[0090] Experiment 2:

[0091] Under nitrogen protection, 1-(4-methylphenyl)-2-(4-methoxyphenyl) disulfide (1.0 mmol), Pd2(dba)3(0.02 mmol), dppb (0.04 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the mixture was reacted at 90°C for 20 hours. After the reaction was completed, the target product 1-(4-methylphenyl)-2-(4-methoxyphenyl) sulfide (1.0 mmol) was separated by column chromatography, and was a colorless liquid with a yield of 85%.

[0092] From the two experiments of Example 3, it can be seen that even if Ar 1 ≠ Ar 2 , and are of different types, the yield remains at a high level.

[0093] Example 4:

[0094] When the catalyst is a Ni catalyst:

[0095] Under nitrogen protection, diphenyl disulfide (1.0 mmol), Ni(Ph3P)2Cl2(0.05 mmol), lithium tert-butoxide (2.0 mmol), zinc powder (4.0 mmol) and tetrahydrofuran (2.0 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the mixture was reacted at 90°C for 4 hours. After the reaction was completed, the target product diphenyl sulfide was separated by column chromatography, and was a colorless liquid with a yield of 39%.

[0096] Example 4-1:

[0097] In Example 4, under the same conditions, the metal catalyst Ni(Ph3P)2Cl2was replaced by Ni(cod)2, and the yield was 40%.

[0098] Example 5:

[0099] When the catalyst uses a Pt catalyst:

[0100] Experiment 1: Under nitrogen protection, diphenyl disulfide (1.0 mmol), Pt(Ph3P)4(0.05 mmol), lithium tert-butoxide (2.2 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2.0 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the reaction was carried out at 90°C overnight. After the reaction was completed, the target product diphenyl sulfide was separated by column chromatography, and was a colorless liquid with a yield of 10%.

[0101] Experiment 2: Under nitrogen protection, diphenyl disulfide (1.0 mmol), PtCl2(0.05 mmol), lithium tert-butoxide (2.2 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2.0 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the reaction was carried out at 90°C overnight. After the reaction was completed, the target product diphenyl sulfide was separated by column chromatography, and was a colorless liquid with a yield of 15%.

[0102] Example 6:

[0103] When the catalyst uses a Rh catalyst:

[0104] Under nitrogen protection, diphenyl disulfide (1.0 mmol), Rh(Ph3P)3Cl (0.05 mmol), lithium tert-butoxide (2.2 mmol), zinc powder (2.0 mmol) and tetrahydrofuran (2.0 mL) were sequentially added into a 25 mL Schlenk tube, and after mixing and stirring, the reaction was carried out at 90°C overnight. After the reaction was completed, the target product diphenyl sulfide was separated by column chromatography, and was a colorless liquid with a yield of 28%.

[0105] Example 6-1:

[0106] In Example 6, under the same conditions, the metal catalyst Rh(Ph3P)3Cl was replaced by Rh(dba)3, and the yield was 30%.

[0107] From Example 4, Example 5 and Example 6, it can be seen that when the metal catalyst is a Ni catalyst, a Pt catalyst and a Rh catalyst, there is still a certain yield; so that the selection of the metal catalyst is more diverse.

[0108] The above only describes the preferred embodiments of the present application and is not used to limit the present application, and any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application shall be included in the protection scope of the present application.

Claims

1. A method for preparing a diaryl sulfide compound, characterized in that: Includes the following steps: S1: Under anhydrous and oxygen-free conditions, a diaryl disulfide, a catalyst, and a ligand with the structure shown in formula (I) are added to the reactor; S2: Add alkali, metal and organic solvent to S1; react in a sealed environment at a certain temperature and then undergo post-treatment to obtain diaryl sulfide compounds with the structure shown in formula (II); Among them, Ar 1 and Ar 2 Individually, they are substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, and substituted or unsubstituted heterocyclic aryl groups containing N, O, or S atoms; Ar 1 and Ar 2 Same or different; The substituted groups on phenyl, naphthyl, and heterocyclic aryl groups containing N, O, or S atoms include mono- or poly-substituted C6-C groups (ortho-, meta-, and para-substituted). 20 Long-chain alkyl groups, or C6-C groups including ortho, meta, and para substituted or polysubstituted groups. 20 Branched alkyl groups, or C6-C groups including ortho, meta, and para substituted or polysubstituted groups. 20 Long-chain alkoxy groups, or C6-C groups including ortho, meta, and para substituted or polysubstituted groups. 20 The branched alkoxy group, or including one or more of chlorine, ester, aldehyde, trifluoromethyl, cyano, amino and phenyl groups; The catalyst is any one or a mixture of two of the following metal catalysts: nickel, palladium, platinum, and rhodium. The ligands include one or more of bidentate phosphine ligands and monodentate phosphine ligands; The metal is Zn; The nickel catalyst is selected from any one or more of the following: nickel dichloride of bis(triphenylphosphine), nickel dichloride of (1,1'-bis(diphenylphosphine)ferrocene), nickel dichloride of 1,3-bis(diphenylphosphine propane), nickel dichloride of bis(1,5-cyclooctadiene), nickel tetra(triphenylphosphine), nickel chloride, and nickel bromide. The palladium catalyst is any one or more of tris(dibenzylacetone)palladium, (dibenzylacetone)palladium, tetra(triphenylphosphine)palladium, palladium acetate, palladium chloride, palladium bromide, 1,1'-bis(diphenylphosphine)ferrocene palladium(II), 1,4-bis(diphenylphosphinebutane)palladium(II) and bistriphenylphosphinepalladium(II); The platinum catalyst is any one or both of platinum chloride and tetra(triphenylphosphine)platinum; The rhodium catalyst is any one or more of tris(triphenylphosphine) rhodium chloride, tetracarbonyl dirhodium chloride, and tris(dibenzylideneacetone) rhodium.

2. The method for preparing a diaryl sulfide compound according to claim 1, characterized in that: The molar ratio of the catalyst to diaryl disulfide is 0.1%-20%.

3. The method for preparing a diaryl sulfide compound according to claim 1, characterized in that: Monodentate phosphine ligands include one or more of triphenylphosphine, tricyclohexylphosphine, diphenylmethylphosphine, and phenyldimethylphosphine; bidentate phosphine ligands include one or more of bis(diphenylphosphinemethane), bis(diphenylphosphineethane), bis(diphenylphosphinepropane), bis(diphenylphosphinebutane), bis(diphenylphosphinehexane), 1,1'-bis(diphenylphosphine)ferrocene, 1,1'-binaphthyl-2,2'-bis(diphenylphosphine), and 4,5-bis(diphenylphosphine)-9,9-dimethyloxane.

4. The method for preparing a diaryl sulfide compound according to claim 1, characterized in that: The alkali is one or more combinations of lithium tert-butoxide, lithium methoxide, lithium ethanol, hexamethyldisilamide lithium, diisopropylamide lithium, potassium tert-butoxide, sodium tert-butoxide, sodium carbonate, potassium carbonate, lithium carbonate, sodium methoxide, and sodium ethanol.

5. The method for preparing a diaryl sulfide compound according to claim 1, characterized in that: The organic solvent is selected from one or any mixture of tetrahydrofuran, acetonitrile, and DMF.

6. The method for preparing a diaryl sulfide compound according to claim 1, characterized in that: The reaction temperature is 50℃-150℃, and the reaction time is 4-24h.

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