A method for electrophilic cross-coupling of aryl perfluorobutyl sulfonates with aryl bromides

Abstract

The application discloses an electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide, and belongs to the technical field of organic compound synthesis. The aryl perfluorobutyl sulfonate compound and the aryl bromide are subjected to an electrophilic cross-coupling reaction under the action of a catalyst, a ligand and a metal in a solvent to obtain a target compound. The reaction uses the cheap and easily obtained aryl perfluorobutyl sulfonate as a coupling substrate, can not only reduce reaction steps, but also avoid using an organic metal compound which is prepared in advance and is sensitive to water and air, and provides a new method for synthesis of biaryl. The preparation method has the characteristics of mild reaction condition, simple post-treatment, green step, low pollution, high economic benefit and the like.

Description

Technical Field

[0001] This invention belongs to the field of organic compound synthesis technology, specifically relating to a method for electrophilic cross-coupling of aryl perfluorobutyl sulfonate and aryl bromine. Background Technology

[0002] In recent decades, the cross-coupling reaction of two electrophiles has proven to be a simple and practical strategy for the convenient synthesis of organic compounds with high structural diversity. Aryltrifluoromethanesulfonate (ArOSO2CF3) has been widely used as an excellent electrophile in synthesis. The electron-withdrawing ability of the -OSO2CF3 group is crucial for the rapid insertion of Pd(0) into the CO bond of aryltrifluoromethanesulfonate.

[0003] Because aryl trifluoromethanesulfonates have moderate reactivity and the functional groups of trifluoromethanesulfonates are relatively expensive, aryl fluorosulfonates have been proposed as alternatives to trifluoromethanesulfonates. These sulfonates exhibit similar reactivity to aryl trifluoromethanesulfonates and produce excellent results in various cross-coupling reactions. However, fluorosulfonic anhydrides, which are not widely commercialized, have toxicity comparable to phosgene and should be handled with care. Furthermore, aryl fluoroalkyl sulfonates (ArOSO2(CF2)...) n CF3) can be readily prepared using commercially available fluoroalkyl sulfonic anhydrides or halides. Particularly attractive are aryl perfluorobutyl sulfonates (ArONf = ArOSO2C4F9), which are easy to prepare, relatively stable, and readily purified by rapid column chromatography. Furthermore, they are readily prepared from phenols and inexpensive industrial products, making them cost-effective. Summary of the Invention

[0004] The purpose of this section is to outline some aspects of embodiments of the present invention and to briefly describe some preferred embodiments. Simplifications or omissions may be made in this section, as well as in the abstract and title of this application, to avoid obscuring the purpose of these documents; however, such simplifications or omissions should not be construed as limiting the scope of the invention.

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

[0006] One objective of this invention is to provide a method for electrophilic cross-coupling of aryl perfluorobutyl sulfonate with aryl bromide, which has mild reaction conditions and features simple post-processing, green steps, low pollution, and high economic benefits.

[0007] To solve the above-mentioned technical problems, the present invention provides the following technical solution: a method for electrophilic cross-coupling of aryl perfluorobutyl sulfonate and aryl bromine, comprising: carrying out an electrophilic cross-coupling reaction of aryl perfluorobutyl sulfonate compound I represented by formula I and aryl bromine represented by formula II in a solvent under the action of a catalyst, a ligand and a metal, to obtain the compound represented by formula III;

[0008] Ar-OSO2C4F9 (Formula I);

[0009] Ar′-Br (Formula II);

[0010] Ar-Ar′ (Formula III);

[0011] Ar includes one of the following: halogen, trifluoromethoxy, trifluoromethyl, methyl, allyl, N,N-dimethylamino, naphthalene substituent, and quinoline substituent.

[0012] Ar' includes one of the following: phenyl, methyl-substituted phenyl, methoxy-substituted phenyl, benzyloxy-substituted phenyl, dimethyl tert-butylsiloxy-substituted phenyl, amino-substituted phenyl, 1,2-methylenedioxyphenyl-substituted, and dibenzo[b,d]furan-substituted.

[0013] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide of the present invention, wherein 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, naphth-1-yl perfluorobutyl sulfonate, naphth-2-yl perfluorobutyl sulfonate, and quinoline-8-yl perfluorobutyl sulfonate.

[0014] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide of the present invention, wherein the aryl bromide includes 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 perfluorobutyl sulfonate and aryl bromine of the present invention, wherein the molar ratio of the aryl perfluorobutyl sulfonate compound to the aryl bromine is 1:3.

[0016] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide of the present invention, the catalyst comprises one of ferrous chloride, chromium trichloride, nickel chloride, nickel dichloride of bis(triphenylphosphine), copper chloride, nickel bromide, nickel iodide, cobalt dichloride of bis(triphenylphosphine), palladium dichloride of bis(triphenylphosphine), and nickel acetylacetonate.

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

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

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

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

[0021] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromide of the present invention, the solvent includes 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 aryl perfluorobutyl sulfonate and aryl bromine of the present invention, wherein: the direct cross-coupling reaction is carried out at a reaction temperature of 25-60°C; preferably, the temperature is 25°C.

[0023] As a preferred embodiment of the electrophilic cross-coupling method of aryl perfluorobutyl sulfonate and aryl bromine of the present invention, the method further includes a step of purifying the obtained target compound.

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

[0025]

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

[0027] This invention provides a novel method for the electrophilic cross-coupling of aryl perfluorobutyl sulfonate with aryl bromide. This reaction utilizes inexpensive and readily available aryl perfluorobutyl sulfonate as the coupling substrate, which not only reduces the number of reaction steps but also avoids the use of moisture-sensitive organozinc reagents and toxic organotin compounds, providing a new method for the synthesis of biaryl compounds. The preparation method of this invention features mild reaction conditions, simple post-processing, green procedures, low pollution, and high economic efficiency. Attached Figure Description

[0028] To more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings used in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort. Wherein:

[0029] Figure 1 The proton NMR spectrum of 4-methoxy-1,1'-biphenyl, the target product of Example 1 of the present invention;

[0030] Figure 2 The carbon spectrum of 4-methoxy-1,1'-biphenyl, the target product of Example 1 of this invention.

[0031] Figure 3 The 1H NMR spectrum of the target product 4-methoxy-4'-methyl-1,1'-biphenyl in Example 2 of this invention;

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

[0033] Figure 5 The 1H N-dimethyl-[1,1'-biphenyl]-4-amine, the target product of Example 3 of this invention;

[0034] Figure 6 The carbon spectrum of N,N-dimethyl-[1,1'-biphenyl]-4-amine, the target product of Example 3 of the present invention. Detailed Implementation

[0035] To make the above-mentioned objects, features and advantages of the present invention more apparent and understandable, the specific embodiments of the present invention will be described in detail below with reference to the examples in the specification.

[0036] Many specific details are set forth in the following description in order to provide a full understanding of the invention. However, the invention may also be practiced in other ways different from those described herein, and those skilled in the art can make similar extensions without departing from the spirit of the invention. Therefore, the 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 phrase "in one embodiment" appearing in different places in this specification does not necessarily refer to the same embodiment, nor is it a single or selective embodiment that is mutually exclusive with other embodiments.

[0038] The 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, all other raw materials used in the examples were commercially purchased.

[0041] Example 1

[0042] (1) Place the sealed tube equipped with a magnetic stirrer in an oven to dry for one hour. After taking it out, while it is still hot, plug it with a rubber stopper 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, under reduced pressure, heat the mixture of magnesium chips and lithium chloride with an electric heating gun (320 °C, 3 minutes).

[0043] (2) After the mixture cooled to room temperature, 2 mL of ultra-dry tetrahydrofuran was added, and the sealing tube was evacuated with nitrogen three times. Then, 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-diphenylphosphine) ether (26.9 mg, 0.05 mmol, 10 mol%) were added to the sealing tube respectively; the mixture was stirred at room temperature for 12 hours.

[0044] (3) Subsequently, the product was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried with 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: 300-400 mesh silica gel powder as the stationary phase and petroleum ether as the mobile phase. Finally, 79.2 mg of the target product was obtained.

[0045] The target product was characterized as follows: Figure 1 and 2 As shown, 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] Characterization data showed that the target product obtained was 4-methoxy-1,1'-biphenyl (purity > 98%); the calculated yield was 86%. The structural formula of the target product 4-methoxy-1,1'-biphenyl is as follows:

[0047]

[0048] Example 2

[0049] (1) Place the sealed tube equipped with a magnetic stirrer in an oven to dry for one hour. After taking it out, while it is still hot, plug it with a rubber stopper 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, under reduced pressure, heat the mixture of magnesium chips and lithium chloride with an electric heating gun (320 °C, 3 minutes).

[0050] (2) After the mixture cooled to room temperature, 2 mL of ultra-dry tetrahydrofuran was added, and the sealing tube was evacuated 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-diphenylphosphine) ether (26.9 mg, 0.05 mmol, 10 mol%) were added to the sealing tube respectively; the mixture was stirred at room temperature for 12 hours.

[0051] (3) Subsequently, the product was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried with 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: 300-400 mesh silica gel powder as the stationary phase and petroleum ether as the mobile phase. Finally, 54.5 mg of the target product was obtained.

[0052] The target product was characterized as follows: Figure 3 and 4 As shown, the result is: a 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] Characterization data showed that the target product obtained was 4-methoxy-4'-methyl-1,1'-biphenyl (purity > 98%); the calculated yield was 55%. The structural formula of the target product 4-methoxy-4'-methyl-1,1'-biphenyl is as follows:

[0054]

[0055] Example 3

[0056] (1) Place the sealed tube equipped with a magnetic stirrer in an oven to dry for one hour. After taking it out, while it is still hot, plug it with a rubber stopper 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, under reduced pressure, heat the mixture of magnesium chips and lithium chloride with an electric heating gun (320 °C, 3 minutes).

[0057] (2) After the mixture cooled to room temperature, 2 mL of ultra-dry tetrahydrofuran was added, and the sealing tube was evacuated with nitrogen three times. Then, 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-diphenylphosphine) ether (26.9 mg, 0.05 mmol, 10 mol%) were added to the sealing tube respectively; the mixture was stirred at room temperature for 12 hours.

[0058] (3) Subsequently, the product was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried with 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: 300-400 mesh silica gel powder as the stationary phase and petroleum ether as the mobile phase. Finally, 66.1 mg of the target product was obtained.

[0059] The target product was characterized as follows: Figure 5 and 6 As shown, the result is: a 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] Characterization data revealed that the target product was N,N-dimethyl-[1,1'-biphenyl]-4-amine (purity > 98%); the calculated yield was 67%. The structural formula of the target product N,N-dimethyl-[1,1'-biphenyl]-4-amine is as follows:

[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 shown in Table 1, under the same reaction conditions, using different solvents, we found that this reaction could not proceed in organic solvents such as DMSO, DMF, DME, and NMP. When we used 2-MeTHF as the reaction solvent, we were able to obtain the target product in a 39% yield. When we used THF as the solvent, the reaction effect was the best, obtaining the target product in a 81% separation yield. Therefore, THF was ultimately determined to be the optimal solvent for the template reaction.

[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] Table 2 shows that, under the same reaction conditions, using different catalysts, NiCl2 was found to achieve a separation yield of 69% for the desired product. In contrast, the use of other metal catalysts, including FeCl2, CrCl3, CrCl2, and Co(PPh3)2Cl2, all resulted in product separation yields below 60%. Subsequently, nickel catalysts were screened; experimental results showed that all nickel catalysts could yield the desired product, with Ni(PPh3)2Cl2 being the most ideal catalyst for this reaction system, increasing the product separation yield to 81%.

[0074] Example 6

[0075] Example 6 is basically the same as Example 1, except that the ligand added in step (1) is different, 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 using nitrogen ligands. Among them, the reaction effect is the 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] This invention provides a novel nickel-catalyzed site-affinity cross-coupling reaction of aryl perfluorobutyl sulfonate with aryl bromide. This reaction utilizes inexpensive and readily available aryl perfluorobutyl sulfonate as the coupling substrate, which not only reduces the number of reaction steps but also avoids the use of pre-prepared organometallic compounds that are sensitive to water and air, thus providing a new method for the synthesis of biaryl compounds. The preparation method of this invention features mild reaction conditions, simple post-processing, environmentally friendly procedures, low pollution, and high economic efficiency.

[0087] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit it. Although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art should understand that modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, and all such modifications or substitutions should be covered within the scope of the claims of the present invention.

Claims

1. A method for electrophilic cross-coupling of aryl perfluorobutyl sulfonate with aryl bromide, characterized in that: include, The aryl perfluorobutyl sulfonate compound shown in Formula I and the aryl bromide shown in Formula II were subjected to an electrophilic cross-coupling reaction in a solvent under the action of a catalyst, ligand and metal to obtain the compound shown in Formula III. (Formula I); (Formula II); (Formula III); Wherein, the aryl perfluorobutyl sulfonate compound represented by Formula I is 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, naphth-1-yl perfluorobutyl sulfonate, naphth-2-yl perfluorobutyl sulfonate, and quinoline-8-yl perfluorobutyl sulfonate; The aryl bromide represented by Formula II is 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; The catalyst is one of the following: ferrous chloride, chromium trichloride, nickel chloride, nickel dichloride of bis(triphenylphosphine), copper chloride, nickel bromide, nickel iodide, cobalt dichloride of bis(triphenylphosphine), and nickel acetylacetonate. The ligand is bis(2-diphenylphosphine) ether; The solvent is one of tetrahydrofuran and 2-methyltetrahydrofuran; The metal is magnesium powder.

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

3.

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

20.

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

20.

5. The method for electrophilic cross-coupling of aryl perfluorobutyl sulfonate and aryl bromide as described in any one of claims 1 to 4, characterized in that: The molar ratio of the metal to the aryl perfluorobutyl sulfonate compound is 1 to 5:

1.

6. The method for electrophilic cross-coupling of aryl perfluorobutyl sulfonate and aryl bromide as described in any one of claims 1 to 4, characterized in that: The reaction is carried out at a temperature of 25~60℃.

7. The method for electrophilic cross-coupling of aryl perfluorobutyl sulfonate and aryl bromide as described in any one of claims 1 to 4, characterized in that: It also includes a step of purifying the obtained target compound.

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