A method for synthesizing indane-substituted polyfluorinated arenes

Abstract

The application discloses a synthesis method of indane-substituted polyfluoroarene, and the method uses 2-iodostyrene compound, 7-oxanorbornadiene and polyfluoroarene as raw materials, and reacts in an organic solvent under the joint action of a palladium catalyst, a ligand, a base and an additive, and after reaction, post-treatment is performed to obtain the indane-substituted polyfluoroarene compound; a reaction formula is as follows: in the formula, R 1 one selected from a hydrogen atom, an alkyl group, an alkoxy group, an aryl group and a halogen; 2 one selected from a hydrogen atom, an alkyl group, an alkoxy group, an ester group, an acyl group and a cyano group; R is an alkyl group; and n is the number of fluorine atoms in the polyfluoroarene. The method uses the easily-prepared 2-iodostyrene compound and the commercialized 7-oxanorbornadiene and polyfluoroarene as raw materials, constructs one indane ring and three carbon-carbon bonds through a one-pot method, and realizes fast construction of the indane-substituted polyfluoroarene skeleton. The reaction has the advantages of simple operation, easy availability of raw materials, wide applicability of substrates and easy separation of target products.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of indane alkyl substituted polyfluoroarene. BACKGROUND

[0002] Alkylated polyfluoroarenes are ubiquitous in natural products and bioactive molecules, and have attracted extensive attention in the fields of medicine, dyes, pesticides, biology, etc. Among them, the strategy of palladium-catalyzed intramolecular cascade cyclization / polyfluoroarene alkylation has been highly valued. For example, in 2016, Liang's group reported a palladium-catalyzed intramolecular Heck / intermolecular C-H alkylation reaction of polyfluoroarene with o-iodoaniline-derived acrylamide. Subsequently, the group realized the alkylation of polyfluoroarene through the Narasaka-Heck reaction. Using a similar strategy, Zhang's group established a Pd / XuPhos catalytic system for the enantioselective cascade Heck / intermolecular C-H alkylation reaction of o-iodophenol-derived allyl ether with various polyfluoroarenes. However, these methods are limited by the use of o-iodophenol allyl ether or aryl acrylamide as the reaction substrate, and have the problems of limited substrate range, difficulty in preparation, relatively single synthesis method and poor product diversity. SUMMARY

[0003] In view of the above problems in the prior art, the purpose of the present application is to provide a synthesis method of indane alkyl substituted polyfluoroarene compound, which uses simple and readily available reaction materials to synthesize indane alkyl substituted polyfluoroarene compound through palladium-catalyzed intermolecular cascade cyclization alkylation reaction process in one pot.

[0004] To achieve the above-mentioned purpose, the present application adopts the following technical solutions:

[0005] A synthesis method of indane alkyl substituted polyfluoroarene, which uses 2-iodostyrene compound, 7-oxanorbornadiene and polyfluoroarene as raw materials, and reacts in the presence of palladium catalyst, ligand, base and additive in an organic solvent. After the reaction is completed, the indane alkyl substituted polyfluoroarene compound is obtained after post-treatment.

[0006] The reaction formula of the synthesis method is as follows:

[0007]

[0008] In the formula, R 1 is selected from one of hydrogen atom, alkyl, alkoxy, aryl and halogen; R 2 is selected from one of hydrogen atom, alkyl, alkoxy, ester group, acyl group and cyano group; R is alkyl; and n is the number of fluorine atoms in the polyfluoroarene.

[0009] Preferably, R1 one selected from the group consisting of hydrogen atom, methyl, methoxy, phenyl, trifluoromethyl, fluorine, chlorine; R in polyfluoroarene is one selected from the group consisting of hydrogen atom, methyl, methoxy, acetyl, tert-butyl acrylate, cyano, tert-butyl dimethylsilyloxymethyl; R is one selected from the group consisting of methyl, ethyl, propyl or n-butyl; n is 3, 4 or 5. 2 one selected from the group consisting of hydrogen atom, methyl, methoxy, phenyl, trifluoromethyl, fluorine, chlorine; R in polyfluoroarene is one selected from the group consisting of hydrogen atom, methyl, methoxy, acetyl, tert-butyl acrylate, cyano, tert-butyl dimethylsilyloxymethyl; R is one selected from the group consisting of methyl, ethyl, propyl or n-butyl; n is 3, 4 or 5.

[0010] Preferably, the palladium catalyst is one selected from the group consisting of palladium acetate, palladium chloride, palladium trifluoroacetate, bis(tricyclohexylphosphine)palladium dichloride and bis(acetonitrile)palladium dichloride.

[0011] Preferably, the ligand is one selected from the group consisting of triphenylphosphine, tri(p-methylphenyl)phosphine, tri(p-methoxyphenyl)phosphine, tri(p-fluorophenyl)phosphine, tricyclohexylphosphine tetrafluoroborate, tri-tert-butylphosphine tetrafluoroborate, 1,2-bis(diphenylphosphino)ethane, bis(diphenylphosphino)methane, 1,4-bis(diphenylphosphino)butane, 1,3-bis(diphenylphosphino)propane and 4,5-bisdiphenylphosphino-9,9-dimethylxanthene.

[0012] Preferably, the base is one selected from the group consisting of cesium carbonate, cesium acetate, potassium carbonate, sodium acetate, potassium phosphate, triethylamine and diisopropylamine.

[0013] Preferably, the organic solvent is one selected from the group consisting of ethylene glycol dimethyl ether, toluene, dioxane, acetonitrile, tetrahydrofuran and 1,2-dichloroethane.

[0014] Preferably, the additive is one selected from the group consisting of silver carbonate, silver acetate, silver nitrate and cuprous iodide.

[0015] Preferably, the molar ratio of the 2-iodostyrene compound, 7-oxanorbornadiene, polyfluoroarene, palladium catalyst, ligand, base and additive is 0.1:0.2:0.3:0.01:0.02:0.3:0.2, and the concentration of the 2-iodostyrene compound in the reaction solution is 0.1 mol / L.

[0016] Preferably, the reaction temperature is 110-150℃, and the reaction time is 10-24h, more preferably 130℃ for 16h.

[0017] Preferably, the post-treatment step is as follows: after the reaction is completed, the reaction system is cooled, the organic solvent is removed by rotary evaporation under reduced pressure, concentrated, the residue is mixed with silica gel and separated by column chromatography elution to obtain the indane group-substituted polyfluoroarene compound; the eluent for column chromatography elution is a mixture of petroleum ether and ethyl acetate in a volume ratio of 200:1 to 10:1.

[0018] Compared with the prior art, the present application has the following advantages:

[0019] 1. The present invention has the advantages of low reaction cost, safe and readily available raw materials, good functional group tolerance, and broad substrate universality;

[0020] 2. A variety of indane-substituted polyfluoroaromatic compounds were obtained, not limited to nitrogen or oxygen heterocyclic frameworks, thus expanding the range of alkylated polyfluoroaromatics.

[0021] 3. This invention effectively combines the indene ring skeleton with polyfluoroaromatics, providing a convenient and effective strategy for preparing bioactive molecules containing this similar skeleton. Attached Figure Description

[0022] Figure 1 The 1H NMR spectrum of the product structure in Example 1;

[0023] Figure 2 The 1H NMR spectrum of the product structure in Example 2;

[0024] Figure 3 The 1H NMR spectrum of the product structure in Example 3;

[0025] Figure 4 The 1H NMR spectrum of the product structure in Example 4;

[0026] Figure 5 The 1H NMR spectrum of the product structure in Example 5;

[0027] Figure 6 The 1H NMR spectrum of the product structure in Example 6;

[0028] Figure 7 The 1H NMR spectrum of the product structure in Example 7;

[0029] Figure 8 The 1H NMR spectrum of the product structure in Example 8;

[0030] Figure 9 The 1H NMR spectrum of the product structure in Example 9;

[0031] Figure 10 The 1H NMR spectrum of the product structure in Example 10;

[0032] Figure 11 The 1H NMR spectrum of the product structure in Example 11 is shown. Detailed Implementation

[0033] The present invention will be further described below with reference to specific embodiments, but the scope of protection of the present invention is not limited thereto;

[0034] Example 1:

[0035]

[0036] To a 25 mL reaction flask, 1-iodo-2-(prop-1-en-2-yl)benzene (24.3 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 2,3,5,6-tetrafluoroanisole (54.0 mg, 0.3 mmol), bis(tricyclohexylphosphine)palladium dichloride (7.4 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,2-dichloroethane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 16 hours. After the reaction was complete, the solvent was removed by rotary evaporation, and then the target product (51%) was obtained by column chromatography (petroleum ether / ethyl acetate = 100:1 to 50:1, v / v).

[0037] 1 H NMR(400MHz,Chloroform-d)δ7.30(t,J=4.7Hz,1H),7.12(d,J=2.2Hz,3H),6.52(d,J=5.5Hz,1H),6.24(dt,J=5 .3,2.5Hz,1H),3.92(d,J=1.3Hz,3H),3.07(dt,J=13.5,1.8Hz,1H),2.90(dt,J=13.4,1.8Hz,1H),1.29(s,3H).

[0038] Example 2:

[0039]

[0040] To a 25 mL reaction flask, 1-iodo-4-methyl-2-(prop-1-en-2-yl)benzene (25.8 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 2,3,5,6-tetrafluoroanisole (54.0 mg, 0.3 mmol), palladium acetate (2.2 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,2-dichloroethane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 20 hours. After the reaction was complete, the solvent was removed by rotary evaporation, followed by column chromatography (petroleum ether / ethyl acetate = 100:1 to 50:1, v / v) to obtain the target product (52%).

[0041] 1 H NMR(400MHz,Chloroform-d)δ7.20(s,1H),7.10(d,J=7.5Hz,1H),7.02(d,J=7.6Hz,1H),6.57(d,J=5.5Hz,1H),6.24(dd,J=5 .4,2.7Hz,1H),4.01(t,J=1.3Hz,3H),3.14(dt,J=13.4,1.6Hz,1H),2.91(dt,J=13.4,1.6Hz,1H),2.40(s,3H),1.34(s,3H).

[0042] Example 3:

[0043]

[0044] To a 25 mL reaction flask, 4-chloro-2-iodo-1-(prop-1-en-2-yl)benzene (27.8 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 2,3,5,6-tetrafluoroanisole (54.0 mg, 0.3 mmol), bis(tricyclohexylphosphine)palladium dichloride (7.4 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,2-dichloroethane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 16 hours. After the reaction was complete, the solvent was removed by rotary evaporation, followed by column chromatography (petroleum ether / ethyl acetate = 100:1 to 50:1, v / v) to obtain the target product (53%).

[0045] 1 H NMR(400MHz,Chloroform-d)δ7.29(d,J=8.5Hz,1H),7.20–7.12(m,2H),6.53(d,J=5.5Hz,1H),6.40(dt, J=5.3,2.5Hz,1H),4.01(t,J=1.4Hz,3H),3.13(dt,J=13.5,1.8Hz,1H),3.06–2.96(m,1H),1.36(s,3H).

[0046] Example 4:

[0047]

[0048] To a 25 mL reaction flask, 4-fluoro-2-iodo-1-(prop-1-en-2-yl)benzene (26.2 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 2,3,5,6-tetrafluoroanisole (54.0 mg, 0.3 mmol), bis(tricyclohexylphosphine)palladium dichloride (7.4 mg, 0.01 mmol), tri-tert-butylphosphine tetrafluoroborate (5.8 mg, 0.02 mmol), potassium carbonate (41.4 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,2-dichloroethane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 16 hours. After the reaction was complete, the solvent was removed by rotary evaporation, and then the product was separated by column chromatography (petroleum ether / ethyl acetate = 100:1 to 50:1, v / v) to obtain the target product (47%).

[0049] 1 H NMR(400MHz,Chloroform-d)δ7.29(dd,J=9.0,4.9Hz,1H),6.87(ddt,J=9.3,4.6,2.4Hz,2H),6.54(d,J=5.6Hz,1H),6.4 1(dt,J=5.3,2.5Hz,1H),4.01(t,J=1.2Hz,3H),3.13(dt,J=13.5,1.8Hz,1H),3.01(dt,J=13.6,1.9Hz,1H),1.37(s,3H).

[0050] Example 5:

[0051]

[0052] To a 25 mL reaction flask, 2-iodo-1-methyl-3-(prop-1-en-2-yl)benzene (25.8 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 2,3,5,6-tetrafluoroanisole (54.0 mg, 0.3 mmol), bis(tricyclohexylphosphine)palladium dichloride (7.4 mg, 0.01 mmol), 1,4-bis(diphenylphosphine)butane (8.6 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,4-dioxane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 16 hours. After the reaction was complete, the solvent was removed by rotary evaporation, followed by column chromatography (petroleum ether / ethyl acetate = 100:1 to 50:1, v / v) to obtain the target product (62%).

[0053] 1 H NMR(400MHz,Chloroform-d)δ7.20(d,J=7.4Hz,1H),7.11(t,J=7.4Hz,1H),7.02(d,J=7.4Hz,1H),6.72(d,J=5.6Hz,1H),6.31(dt ,J=5.3,2.5Hz,1H),4.01(d,J=1.5Hz,3H),3.14(dt,J=13.5,1.8Hz,1H),2.91(dt,J=13.5,1.9Hz,1H),2.36(s,3H),1.33(s,3H).

[0054] Example 6:

[0055]

[0056] To a 25 mL reaction flask, 1-(but-1-en-2-yl)-2-iodo-4-methoxybenzene (28.8 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 2,3,5,6-tetrafluoroanisole (54.0 mg, 0.3 mmol), palladium acetate (2.2 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,2-dichloroethane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 16 hours. After the reaction was complete, the solvent was removed by rotary evaporation, followed by column chromatography (petroleum ether / ethyl acetate = 100:1 to 10:1, v / v) to obtain the target product (45%).

[0057] 1 H NMR(400MHz,Chloroform-d)δ7.24–7.15(m,1H),6.72(dq,J=5.1,2.5Hz,2H),6.57(d,J=5.6Hz,1H),6.28(dt,J=5.5,2.6Hz, 1H),3.98(d,J=1.3Hz,3H),3.79(s,3H),3.20–3.10(m,1H),3.08–2.98(m,1H),1.90(q,J=7.4Hz,2H),0.55(t,J=7.4Hz,3H).

[0058] Example 7:

[0059]

[0060] To a 25 mL reaction flask, 1-(but-1-en-2-yl)-2-iodobenzene (25.8 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 2,3,5,6-tetrafluoroanisole (54.0 mg, 0.3 mmol), bis(tricyclohexylphosphine)palladium dichloride (7.4 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,2-dichloroethane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 14 hours. After the reaction was complete, the solvent was removed by rotary evaporation, followed by column chromatography (petroleum ether / ethyl acetate = 200:1 to 50:1, v / v) to obtain the target product (48%).

[0061] 1 H NMR(400MHz,Chloroform-d)δ7.33(q,J=4.2,3.4Hz,1H),7.22–7.14(m,3H),6.63(d,J=5.6Hz,1H),6.25(dt,J=5.4,2.6Hz,1H),3. 98(d,J=1.3Hz,3H),3.17(dt,J=13.5,1.8Hz,1H),3.04(dt,J=13.4,1.8Hz,1H),1.93(qd,J=7.2,2.7Hz,2H),0.54(t,J=7.4Hz,3H).

[0062] Example 8:

[0063]

[0064] To a 25 mL reaction flask, 1-iodo-2-(prop-1-en-2-yl)benzene (24.3 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 1,2,3,5,6-pentafluorobenzene (50.4 mg, 0.3 mmol), palladium trifluoroacetate (3.3 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), potassium phosphate (63.3 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,4-dioxane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 16 hours. After the reaction was complete, the solvent was removed by rotary evaporation, followed by column chromatography (petroleum ether / ethyl acetate = 200:1 to 100:1, v / v) to obtain the target product (60%).

[0065] 1 H NMR(400MHz,Chloroform-d)δ7.43–7.36(m,1H),7.19(t,J=4.0Hz,3H),6.59(d,J=5.6Hz,1H),6.3 1(dt,J=5.4,2.6Hz,1H),3.18(dt,J=13.5,2.0Hz,1H),3.07(dt,J=13.4,2.0Hz,1H),1.40(s,3H).

[0066] Example 9:

[0067]

[0068] To a 25 mL reaction flask, 1-iodo-2-(prop-1-en-2-yl)benzene (24.3 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 1,2,4,5-tetrafluorobenzene (45.0 mg, 0.3 mmol), bis(tricyclohexylphosphine)palladium dichloride (7.4 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of toluene was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 14 hours. After the reaction was complete, the solvent was removed by rotary evaporation, and then the target product (50%) was obtained by column chromatography (petroleum ether / ethyl acetate = 200:1 to 100:1, v / v).

[0069] 1H NMR(400MHz,Chloroform-d)δ7.39(t,J=4.4Hz,1H),7.20(d,J=3.1Hz,3H),6.85(tt,J=9.6,7.4Hz,1H),6.60(d,J =5.5Hz,1H),6.33(dt,J=5.6,2.6Hz,1H),3.22(dq,J=13.3,1.6Hz,1H),3.05(dq,J=13.2,1.6Hz,1H),1.39(s,3H).

[0070] Example 10:

[0071]

[0072] To a 25 mL reaction flask, 1-iodo-2-(prop-1-en-2-yl)benzene (24.3 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), 2,4,5-trifluorobenzonitrile (47.1 mg, 0.3 mmol), bis(tricyclohexylphosphine)palladium dichloride (7.4 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver carbonate (54.8 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of 1,2-dichloroethane was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 12 hours. After the reaction was complete, the solvent was removed by rotary evaporation, followed by column chromatography (petroleum ether / ethyl acetate = 200:1 to 50:1, v / v) to obtain the target product (42%).

[0073] 1 H NMR(400MHz,Chloroform-d)δ7.35–7.30(m,1H),7.16–7.07(m,4H),6.51(d,J=5. 5Hz, 1H), 6.24 (dt, J=5.5, 2.7Hz, 1H), 3.11 (qt, J=13.3, 1.7Hz, 2H), 1.35 (s, 3H).

[0074] Example 11:

[0075]

[0076] To a 25 mL reaction flask, 1-iodo-2-(prop-1-en-2-yl)benzene (24.3 mg, 0.1 mmol), dimethyl 7-oxabicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (42.0 mg, 0.2 mmol), tert-butyldimethyl((2,3,5,6-tetrafluorobenzyl)oxy)silane (88.2 mg, 0.3 mmol), bis(tricyclohexylphosphine)palladium dichloride (7.4 mg, 0.01 mmol), tricyclohexylphosphine tetrafluoroborate (7.4 mg, 0.02 mmol), cesium carbonate (97.8 mg, 0.3 mmol), and silver acetate (33.4 mg, 0.2 mmol) were added sequentially. Then, 1.0 mL of ethylene glycol dimethyl ether was added, the flask was sealed, and the mixture was stirred in an oil bath at 130 °C for 20 hours. After the reaction was complete, the solvent was removed by rotary evaporation, and then the product was separated by column chromatography (petroleum ether / ethyl acetate = 200:1 to 100:1, v / v) to obtain the target product (66%).

[0077] 1 H NMR(400MHz,Chloroform-d)δ7.32(p,J=2.7Hz,1H),7.16–7.04(m,3H),6.52(d,J=5.6Hz,1H),6.26(dt,J=5.3,2.5Hz,1H), 4.65(t,J=1.6Hz,2H),3.14(dt,J=13.3,1.8Hz,1H),2.95(dt,J=13.2,1.8Hz,1H),1.31(s,3H),0.81(s,9H),-0.01(s,6H).

[0078] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A method for synthesizing indane-substituted polyfluoroaromatics, characterized in that: Using 2-iodostyrene, 7-oxanorbornene and polyfluoroaromatics as raw materials, the reaction takes place in an organic solvent under the combined action of palladium catalyst, ligand, base and additives. After the reaction is completed, the indane-substituted polyfluoroaromatic compound is obtained by post-treatment. The reaction formula for the synthesis method is as follows: ； R in the 2-iodostyrene compound 1 Selected from one of hydrogen atom, methyl, methoxy, phenyl, trifluoromethyl, fluorine, chlorine; R in polyfluoroaromatics 2 It is selected from one of hydrogen atom, methyl, benzyloxymethyl, methoxy, acetyl, tert-butyl acrylate, cyano, tert-butyldimethoxymethyl; R is one of methyl, ethyl, propyl or n-butyl; the number of fluorine atoms n in the polyfluoroaromatic hydrocarbon is 3, 4 or 5; The ligand is one of triphenylphosphine, tris(p-methylphenyl)phosphine, tris(p-methoxyphenyl)phosphine, tris(p-fluorophenyl)phosphine, tricyclohexylphosphine tetrafluoroborate, tri-tert-butylphosphine tetrafluoroborate, 1,2-bis(diphenylphosphine)ethane, bis(diphenylphosphine)methane, 1,4-bis(diphenylphosphine)butane, 1,3-bis(diphenylphosphine)propane, and 4,5-bisdiphenylphosphine-9,9-dimethyloxanethene. The additive is one of silver carbonate, silver acetate, silver nitrate, and cuprous iodide.

2. The method for synthesizing indane-substituted polyfluoroaromatics according to claim 1, characterized in that: The palladium catalyst is one of palladium acetate, palladium chloride, palladium trifluoroacetate, bis(tricyclohexylphosphine)palladium dichloride, or bis(acetonitrile)palladium dichloride.

3. The method for synthesizing indane-substituted polyfluoroaromatics according to claim 1, characterized in that: The alkali is one of cesium carbonate, cesium acetate, potassium carbonate, sodium acetate, potassium phosphate, triethylamine, and diisopropylamine.

4. The method for synthesizing indane-substituted polyfluoroaromatics according to claim 1, characterized in that: The organic solvent is one of ethylene glycol dimethyl ether, toluene, dioxane, acetonitrile, tetrahydrofuran, or 1,2-dichloroethane.

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