Electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide

Abstract

The invention discloses an electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide, and belongs to the technical field of organic compound synthesis. The preparation method comprises the following step: carrying out electrophilic cross-coupling reaction on an aryl perfluorobutyl sulfonate compound and aryl bromide in a solvent in the presence of a catalyst under the action of a ligand and metal to obtain a target compound. The reaction uses cheap and easily available aryl perfluorobutyl sulfonate as a coupling substrate, so that the reaction steps can be reduced, the use of organic metal compounds which are prepared in advance and are sensitive to water and air can be avoided, and a new method is provided for synthesis of biaryl. The preparation method disclosed by the invention has the characteristics of mild reaction conditions, simple post-treatment, green steps, low pollution, high economic benefits and the like.

Description

Technical Field

[0001] The invention belongs to the technical field of organic compound synthesis, and specifically relates to an electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide. Background Art

[0002] In recent decades, cross-coupling reactions of two electrophiles have been demonstrated to be a simple and practical strategy for the convenient synthesis of organic compounds with high structural diversity. Aryl triflates (ArOSO2CF3) have been widely used as a good electrophile for synthesis. The electron-withdrawing ability of the -OSO2CF3 group is crucial for the rapid insertion of Pd(0) into the CO bond of aryl triflates.

[0003] Aryl fluorosulfonates have been proposed as alternatives to triflates due to their modest reactivity and the high cost of the triflate functional group. These sulfonates exhibit similar reactivity to aryl triflates and produce superior results in various cross-coupling reactions. However, fluorosulfonic anhydrides, which are not widely commercialized, have toxicity comparable to that of phosgene and should be handled with care. Furthermore, aryl fluoroalkanesulfonates (ArOSO2(CF2) n CF3) can be easily prepared using commercially available fluoroalkanesulfonic anhydrides or halides. Particularly attractive are aryl perfluorobutyl sulfonates (ArONf = ArOSO2C4F9), which are easy to prepare, relatively stable, and can be easily purified by rapid column purification. Moreover, they are easily prepared from phenols and cheap industrial products at low cost. Summary of the invention

[0004] The purpose of this section is to summarize some aspects of embodiments of the present invention and briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section and the specification abstract and the invention title of this application to avoid blurring the purpose of this section, the specification abstract and the invention title, and such simplifications or omissions cannot be used to limit the scope of the present invention.

[0005] In view of the above problems and / or the problems existing in the prior art, the present invention is proposed.

[0006] One of the purposes of the present invention is to provide an electrophilic cross-coupling method for aromatic perfluorobutyl sulfonate and aromatic bromide, which has the characteristics of mild reaction conditions, simple post-treatment, green steps, low pollution, high economic benefits, etc.

[0007] In order to solve the above technical problems, the present invention provides the following technical solutions: a method for electrophilic cross-coupling of an aryl perfluorobutyl sulfonate and an aryl bromide, comprising: subjecting an aryl perfluorobutyl sulfonate compound I shown in formula I and an aryl bromide shown in formula II to an electrophilic cross-coupling reaction in a solvent under the action of a catalyst, a ligand and a metal to obtain a compound shown in formula III;

[0008] Ar-OSO2C4F9 (Formula I);

[0009] Ar′-Br (Formula II);

[0010] Ar-Ar′ (Formula III);

[0011] Wherein, Ar includes one of halogen, trifluoromethoxy, trifluoromethyl, methyl, allyl, N,N-dimethylamino, naphthyl substituent, and quinoline substituent.

[0012] Ar' includes one of phenyl, methyl substituted phenyl, methoxy substituted phenyl, benzyloxy substituted phenyl, dimethyl tert-butylsilyloxy substituted phenyl, amino substituted phenyl, 1,2-methylenedioxybenzene substituent, and dibenzo[b,d]furan substituent.

[0013] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide of the present invention, the aryl perfluorobutyl sulfonate compound includes one of 4-(trifluoromethyl)phenyl perfluorobutyl sulfonate, 4-fluorophenyl perfluorobutyl sulfonate, 4-chlorophenyl perfluorobutyl sulfonate, 4-(trifluoromethoxy)phenyl perfluorobutyl sulfonate, 4-methylphenyl perfluorobutyl sulfonate, 2-methylphenyl perfluorobutyl sulfonate, 4-vinylphenyl perfluorobutyl sulfonate, 3-(dimethylamino)phenyl perfluorobutyl sulfonate, naphthalene-1-yl perfluorobutyl sulfonate, naphthalene-2-yl perfluorobutyl sulfonate and quinoline-8-yl perfluorobutyl sulfonate.

[0014] As a preferred embodiment of the electrophilic cross-coupling method of aromatic perfluorobutyl sulfonate and aromatic bromide of the present invention, the aromatic bromide comprises one of 1-bromo-2-methoxybenzene, 1-bromo-3-methoxybenzene, 1-bromo-4-methoxybenzene, 1-bromo-3,4-dimethoxybenzene, 4-bromo-2-methyl-1-methoxybenzene, 1-(benzyloxy)-4-bromobenzene, (4-bromophenoxy)(tert-butyl)dimethylsilane, 4-bromo-1,2-methylenedioxybenzene, 6-bromo-1,4-benzoxane, 4-bromo-N,N-diphenylaniline, 4-bromo-N,N-dimethylaniline and 2-bromodibenzo[b,d]furan.

[0015] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide of the present invention, the molar ratio of the aryl perfluorobutane sulfonate compound to the aryl bromide is 1:3.

[0016] As a preferred embodiment of the electrophilic cross-coupling method of aromatic perfluorobutyl sulfonate and aromatic bromide of the present invention, the catalyst comprises one of ferrous chloride, chromium trichloride, nickel chloride, bistriphenylphosphine nickel dichloride, cupric chloride, nickel bromide, nickel iodide, bistriphenylphosphine cobalt dichloride, bistriphenylphosphine palladium dichloride and nickel acetylacetonate.

[0017] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide of the present invention, the molar ratio of the catalyst to the aryl perfluorobutane sulfonate compound is 1 to 3:20, and the preferred molar ratio is 1:20.

[0018] As a preferred embodiment of the electrophilic cross-coupling method of aromatic perfluorobutyl sulfonate and aromatic bromide of the present invention, the ligand comprises one of tricyclohexylphosphine, 2,2'-bipyridine, 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl, bis(2-diphenylphosphophenyl)ether, 1,3-bis(diphenylphosphine)propane, 2,9-dimethyl-1,10-phenanthroline, 1,1'-bis(diphenylphosphine)ferrocene, 1,1,1-tris(diphenylphosphinomethyl)ethane, and 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl.

[0019] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide of the present invention, the molar ratio of the ligand to the aryl perfluorobutane sulfonate compound is 1 to 3:20, and the preferred molar ratio is 1:20.

[0020] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide of the present invention, the metal is magnesium powder, and the molar ratio of the magnesium powder to the aryl perfluorobutane sulfonate compound is 1 to 5:1, preferably 3:1.

[0021] As a preferred embodiment of the electrophilic cross-coupling method of aromatic perfluorobutane sulfonate and aromatic bromide of the present invention, the solvent comprises one of tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, N-methylpyrrolidone and dimethyl sulfoxide.

[0022] As a preferred embodiment of the electrophilic cross-coupling method of aromatic perfluorobutane sulfonate and aromatic bromide of the present invention, the direct cross-coupling reaction is carried out at a reaction temperature of 25 to 60° C., preferably 25° C.

[0023] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide of the present invention, it further comprises the step of purifying the obtained target compound.

[0024] In summary, the chemical equation for the optimal reaction conditions of the present invention is as follows:

[0025]

[0026] Compared with the prior art, the present invention has the following beneficial effects:

[0027] The present invention provides a novel method for electrophilic cross-coupling of aryl perfluorobutyl sulfonate and aryl bromide, wherein the reaction uses cheap and readily available aryl perfluorobutyl sulfonate as a coupling substrate, which can not only reduce the reaction steps, but also avoid the use of organic zinc reagents and toxic organic tin compounds that are sensitive to moisture, thereby providing a novel method for the synthesis of biaryl compounds. The preparation method of the present invention has mild reaction conditions, simple post-treatment, green steps, low pollution, high economic benefits, and the like. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without creative labor. Among them:

[0029] Figure 1 This is the hydrogen spectrum of the target product 4-methoxy-1,1'-biphenyl in Example 1 of the present invention;

[0030] Figure 2 This is the carbon spectrum of the target product 4-methoxy-1,1'-biphenyl in Example 1 of the present invention.

[0031] Figure 3 This is the hydrogen spectrum of the target product 4-methoxy-4'-methyl-1,1'-biphenyl in Example 2 of the present invention;

[0032] Figure 4 This is the carbon spectrum of the target product 4-methoxy-4'-methyl-1,1'-biphenyl of Example 2 of the present invention.

[0033] Figure 5 This is the hydrogen spectrum of the target product N,N-dimethyl-[1,1'-biphenyl]-4-amine of Example 3 of the present invention;

[0034] Figure 6 This is the carbon spectrum of the target product N,N-dimethyl-[1,1'-biphenyl]-4-amine of Example 3 of the present invention. DETAILED DESCRIPTION

[0035] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, the specific implementation methods of the present invention are described in detail below in conjunction with the embodiments of the specification.

[0036] In the following description, many specific details are set forth to facilitate a full understanding of the present invention, but the present invention may also be implemented in other ways different from those described herein, and those skilled in the art may make similar generalizations without violating the connotation of the present invention. Therefore, the present invention is not limited to the specific embodiments disclosed below.

[0037] Secondly, the term "one embodiment" or "embodiment" as used herein refers to a specific feature, structure, or characteristic that may be included in at least one implementation of the present invention. The term "in one embodiment" that appears in different places in this specification does not necessarily refer to the same embodiment, nor does it refer to a separate or selective embodiment that is mutually exclusive with other embodiments.

[0038] The raw material aryl perfluorobutyl sulfonate used in the examples was prepared in the laboratory with reference to the following literature:

[0039] [1] J.; Reissig, H. Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal-Catalyzed Reactions. Adv. Synth. Catal. 2009, 351, 2747-2763.

[0040] Unless otherwise specified, other raw materials used in the examples were purchased from commercial sources.

[0041] Example 1

[0042] (1) Place a sealed tube equipped with a magnetic stirrer in an oven and dry for one hour. Take it out and plug it with a rubber stopper while it is still hot and insert a nitrogen balloon. Then weigh magnesium chips (36.5 mg, 1.5 mmol, 3 equiv.) and lithium chloride (42.4 mg, 1.0 mmol, 2 equiv.) and add them to the sealed tube. Then, use an electric heating gun to heat the mixture of magnesium chips and lithium chloride under reduced pressure (320°C, 3 minutes).

[0043] (2) After the mixture cools to room temperature, 2 mL of ultra-dry tetrahydrofuran is added thereto, and then the sealed tube is evacuated and replaced with nitrogen three times. Aryl perfluorobutyl sulfonate (188.1 mg, 0.5 mmol, 1 equiv.), bis(triphenylphosphine) nickel dichloride (32.8 mg, 0.05 mmol, 10 mol%), p-bromoanisole (280.5 mg, 1.5 mmol, 3 equiv.), and bis(2-diphenylphosphinophenyl) ether (26.9 mg, 0.05 mmol, 10 mol%) are then added to the sealed tube respectively; the mixture is stirred at room temperature for 12 hours;

[0044] (3) The product was then quenched with a saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The extract was then removed by rotary evaporation. The crude product was purified by silica gel column chromatography. The column chromatography separation conditions were: the stationary phase was 300-400 mesh silica gel powder, and the mobile phase was petroleum ether. Finally, 79.2 mg of the target product was obtained.

[0045] The above target products were characterized, such as Figure 1 and 2 As shown, the result is: white solid; the result is: white solid; 1 H NMR (400MHz, CDCl3): δ7.59–7.51(m,4H),7.43(t,J=7.7Hz,2H),7.36–7.28(m,1H),7.03–6.95(m,2H),3.86(s,3H)ppm. 13 C NMR (100MHz, CDCl3): δ159.1,140.8,133.7,128.7,128.1,126.7,126.6,114.1,55.3ppm.IR (KBr): ν=3033,2961,1606,1522,1488,1251,834,760cm -1 .HRMS(m / z):calcd for C 13 H 13 O[M+H] + 185.0961, found:185.0960.

[0046] According to the characterization data, the target product is 4-methoxy-1,1'-biphenyl (purity> 98%); the product yield is calculated to be 86%. The structural formula of the target product 4-methoxy-1,1'-biphenyl is:

[0047]

[0048] Example 2

[0049] (1) Place a sealed tube equipped with a magnetic stirrer in an oven and dry for one hour. Take it out and plug it with a rubber stopper while it is still hot and insert a nitrogen balloon. Then weigh magnesium chips (36.5 mg, 1.5 mmol, 3 equiv.) and lithium chloride (42.4 mg, 1.0 mmol, 2 equiv.) and add them to the sealed tube. Then, use an electric heating gun to heat the mixture of magnesium chips and lithium chloride under reduced pressure (320°C, 3 minutes).

[0050] (2) After the mixture cools to room temperature, 2 mL of ultra-dry tetrahydrofuran is added thereto, and then the sealed tube is evacuated and replaced with nitrogen three times. Subsequently, 4-methylphenyl perfluorobutyl sulfonate (195.1 mg, 0.5 mmol, 1 equiv.), bis(triphenylphosphine) nickel dichloride (32.8 mg, 0.05 mmol, 10 mol%), p-bromoanisole (280.5 mg, 1.5 mmol, 3 equiv.), and bis(2-diphenylphosphinophenyl) ether (26.9 mg, 0.05 mmol, 10 mol%) are added to the sealed tube respectively; the mixture is stirred at room temperature for 12 hours;

[0051] (3) The product was then quenched with a saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The extract was then removed by rotary evaporation. The crude product was purified by silica gel column chromatography. The column chromatography separation conditions were: the stationary phase was 300-400 mesh silica gel powder, and the mobile phase was petroleum ether. Finally, 54.5 mg of the target product was obtained.

[0052] The above target products were characterized, such as Figure 3 and 4 As shown, the result is: white solid; 1 H NMR (400MHz, CDCl3): δ7.57-7.53(m,2H),7.51-7.47(m,2H),7.29-7.24(m,2H),7.03-6.98(m,2H),3.87(s,3H),2.42(s,3H)ppm. 13 C NMR (100MHz, CDCl3): δ158.8,137.9,136.3,133.6,129.4,127.9,126.5,114.1,55 .3,21.0ppm.IR(KBr):ν=2951,1602,1506,1295,1221,1047,1011,831,698,621cm -1 .HRMS(m / z):calcd for C 14 H 15 O[M+H] + 199.1117, found:199.1124.

[0053] According to the characterization data, the target product is 4-methoxy-4'-methyl-1,1'-biphenyl (purity> 98%); the product yield is calculated to be 55%. The structural formula of the target product 4-methoxy-4'-methyl-1,1'-biphenyl is:

[0054]

[0055] Example 3

[0056] (1) Place a sealed tube equipped with a magnetic stirrer in an oven and dry for one hour. Take it out and plug it with a rubber stopper while it is still hot and insert a nitrogen balloon. Then weigh magnesium chips (36.5 mg, 1.5 mmol, 3 equiv.) and lithium chloride (42.4 mg, 1.0 mmol, 2 equiv.) and add them to the sealed tube. Then, use an electric heating gun to heat the mixture of magnesium chips and lithium chloride under reduced pressure (320°C, 3 minutes).

[0057] (2) After the mixture cools to room temperature, 2 mL of ultra-dry tetrahydrofuran is added thereto, and then the sealed tube is evacuated and replaced with nitrogen three times. Aryl perfluorobutyl sulfonate (188.1 mg, 0.5 mmol, 1 equiv.), bis(triphenylphosphine) nickel dichloride (32.8 mg, 0.05 mmol, 10 mol%), 4-bromo-N,N-dimethylaniline (300.1 mg, 1.5 mmol, 3 equiv.), and bis(2-diphenylphosphinophenyl) ether (26.9 mg, 0.05 mmol, 10 mol%) are then added to the sealed tube respectively; the mixture is stirred at room temperature for 12 hours;

[0058] (3) The product was then quenched with a saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The extract was then removed by rotary evaporation. The crude product was purified by silica gel column chromatography. The column chromatography separation conditions were: the stationary phase was 300-400 mesh silica gel powder, and the mobile phase was petroleum ether. Finally, 66.1 mg of the target product was obtained.

[0059] The above target products were characterized, such as Figure 5 and 6 As shown, the result is: white solid; 1 H NMR (400MHz, CDCl3): δ7.63–7.58(m,2H),7.57–7.53(m,2H),7.47–7.40(m,2H),7.33–7.27(m,1H),6.87–6.82(m,2H),3.02(s,6H)ppm. 13C NMR (100MHz, CDCl3): δ 149.9, 141.2, 128.6, 127.7, 126.3, 126.0, 112.7, 40.6ppm. IR (KBr): ν = 2997, 2902, 2832, 1506, 1216, 1048, 815, 771, 698, 587cm -1 .HRMS(m / z):calcd for C 14 H 16 N[M+H] + 198.1277, found:198.1280.

[0060] According to the characterization data, the target product is N, N-dimethyl-[1,1'-biphenyl]-4-amine (purity> 98%); the product yield is calculated to be 67%. The structural formula of the target product N, N-dimethyl-[1,1'-biphenyl]-4-amine is:

[0061]

[0062] Example 4

[0063] Example 4 is basically the same as Example 1, except that the solvent in step (1) is different, as shown in Table 1 below:

[0064] Table 1

[0065]

[0066]

[0067] As can be seen from Table 1, under the same reaction conditions, using different solvents, we found that the reaction could not be carried out in organic solvents such as DMSO, DMF, DME, and NMP. When we used 2-MeTHF as the reaction solvent, the target product was obtained with a yield of 39%. When we used THF as the solvent, the reaction effect was the best, and the target product was obtained with an isolated yield of 81%. Therefore, it was finally determined that the optimal solvent for the template reaction was THF.

[0068] Example 5

[0069] Example 5 is basically the same as Example 1, except that the catalyst in step (1) is different, as shown in Table 2 below:

[0070] Table 2

[0071]

[0072]

[0073] As can be seen from Table 2, under the same reaction conditions, different catalysts were used and it was found that when NiCl2 was used as a catalyst, the desired target product was obtained with a separation yield of 69%. In contrast, the use of other metal catalysts, including FeCl2, CrCl3, CrCl2, and Co(PPh3)2Cl2, all resulted in a product separation yield of less than 60%. Subsequently, nickel catalysts were screened; the experimental results showed that nickel catalysts could all obtain the desired target product, among which Ni(PPh3)2Cl2 was the most ideal catalyst for the reaction system, and the separation yield of the corresponding product was increased to 81%.

[0074] Example 6

[0075] Example 6 is basically the same as Example 1, except that different ligands are added in step (1), as shown in Table 3 below:

[0076] Table 3

[0077]

[0078]

[0079] As can be seen from Table 3, under the same reaction conditions, using different catalysts, we found that the reaction can be achieved when using nitrogen ligands for the reaction, among which the reaction effect is best when L6 (DPEphos) is used as the ligand, and the product separation yield can reach 91%.

[0080] Example 7

[0081] Example 7 is basically the same as Example 1, except that in step (1), the aryl perfluorobutyl sulfonate is different from the aryl bromide, as shown in Table 5 below:

[0082] Table 5

[0083]

[0084]

[0085]

[0086] The present invention provides a new method for the site-philic cross-coupling reaction of aryl perfluorobutane sulfonate and aryl bromide catalyzed by nickel, which uses cheap and readily available aryl perfluorobutane sulfonate as a coupling substrate, which can not only reduce the reaction steps, but also avoid the use of pre-prepared organic metal compounds that are sensitive to water and air, and provide a new method for the synthesis of biaryl compounds. The preparation method of the present invention has mild reaction conditions, simple post-treatment, green steps, low pollution, high economic benefits, etc.

[0087] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention rather than to limit it. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention may be modified or replaced by equivalents without departing from the spirit and scope of the technical solutions of the present invention, which should all be included in the scope of the claims of the present invention.

Claims

1. A method for electrophilic cross-coupling of an aryl perfluorobutane sulfonate and an aryl bromide, characterized in that: include, The aryl perfluorobutyl sulfonate compound represented by formula I and the aryl bromide represented by formula II are subjected to an electrophilic cross-coupling reaction in a solvent in the presence of a catalyst, a ligand and a metal to obtain a compound represented by formula III; Ar-OSO2C4F9 (Formula I); Ar'-Br (Formula II); Ar-Ar' (Formula III); Wherein, Ar includes one of halogen, trifluoromethoxy, trifluoromethyl, methyl, allyl, N,N-dimethylamino, naphthyl substituent, and quinoline substituent. Ar' includes one of phenyl, methyl substituted phenyl, methoxy substituted phenyl, benzyloxy substituted phenyl, dimethyl tert-butylsilyloxy substituted phenyl, amino substituted phenyl, 1,2-methylenedioxybenzene substituent, and dibenzo[b,d]furan substituent.

2. The electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide according to claim 1, characterized in that: The molar ratio of the aryl perfluorobutane sulfonate compound to the aryl bromide is 1:

3.

3. The electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide according to claim 1 or 2, characterized in that: The catalyst comprises one of ferrous chloride, chromium trichloride, nickel chloride, bistriphenylphosphine nickel dichloride, cupric chloride, nickel bromide, nickel iodide, bistriphenylphosphine cobalt dichloride, bistriphenylphosphine palladium dichloride and nickel acetylacetonate.

4. The electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide as claimed in claim 3, characterized in that: The molar ratio of the catalyst to the aryl perfluorobutyl sulfonate compound is 1 to 3:

20.

5. The electrophilic cross-coupling method of aryl perfluorobutanesulfonate and aryl bromide according to any one of claims 1, 2 and 4, characterized in that: The ligand includes one of tricyclohexylphosphine, 2,2'-bipyridine, 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl, bis(2-diphenylphosphinophenyl) ether, 1,3-bis(diphenylphosphino)propane, 2,9-dimethyl-1,10-phenanthroline, 1,1'-bis(diphenylphosphino)ferrocene, 1,1,1-tris(diphenylphosphinomethyl)ethane, and 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl.

6. The electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide according to claim 5, characterized in that: The molar ratio of the ligand to the aryl perfluorobutyl sulfonate compound is 1 to 3:

20.

7. The electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide according to any one of claims 1, 2, 4, and 6, characterized in that: The metal is magnesium powder, and the molar ratio of the metal to the aromatic perfluorobutyl sulfonate compound is 1 to 5:

1.

8. The electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide according to claim 8, characterized in that: The solvent includes one of tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, N-methylpyrrolidone and dimethyl sulfoxide.

9. The electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide according to any one of claims 1, 2, 4, 6, and 8, characterized in that: The reaction temperature is 25-60°C.

10. The electrophilic cross-coupling method of aryl perfluorobutane sulfonate and aryl bromide according to any one of claims 1, 2, 4, 6, and 8, characterized in that: The method also includes a step of purifying the obtained target compound.

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