CN115305490A - Method for synthesizing fluoroalkyl substituted dibenzosuberone compound by electrooxidation - Google Patents

Abstract

The invention discloses a method for synthesizing fluoroalkyl-substituted dibenzocycloheptanone compounds by electro-oxidation, and relates to the technical field of organic synthesis. It is specifically disclosed that: conducting an electrification reaction between o-propargyl biphenyl compounds and sodium fluoroalkyl sulfinate compounds to obtain fluoroalkyl-substituted dibenzocycloheptanone compounds. In the present invention, o-propargyl biphenyl compounds and sodium fluoroalkyl sulfinate compounds are used as raw materials, and the two are subjected to a constant current electrification reaction in an electrolyte solution. Under specific reaction temperature and current conditions, fluoroalkyl Oxidation of the sulfinate anion to a fluoroalkyl radical, which attacks the carbonyl alpha position of the alkynone reactant to give an alkenyl radical, which is then cyclized to another benzene by 7‑endo‑trig The seven-membered ring is constructed at the ring, and finally the fluoroalkyl-substituted dibenzocycloheptanones are obtained by deprotonation.

Description

Method for electrooxidative synthesis of fluoroalkyl-substituted dibenzocycloheptanone compounds

technical field

The invention relates to the technical field of organic synthesis, in particular to a method for electrooxidatively synthesizing fluoroalkyl-substituted dibenzocycloheptanone compounds.

Background technique

Colchicine is an alkaloid with a variety of physiological activities that has been isolated and utilized for a long time. However, due to its obvious toxic and side effects, it has not been effectively developed and utilized in anti-tumor. However, the natural class colchicine and its analogs (with 6-7-6 polycyclic structure) derived from its structure have been found to have low toxicity and good activity. Dibenzocycloheptane is its core skeleton, representative The compounds are shown below NSC51046, ZD 6126 and N-acetylcoichine.

The direct construction around the dibenzocycloheptanone skeleton became a research interest of synthetic organic chemists decades ago. On the other hand, the introduction of fluorine atoms into drug molecules often leads to improvements in biological activities such as solubility, bioavailability, and thermal stability. In recent years, organic synthetic chemists have carried out a lot of work around introducing fluorine-containing groups into organic molecules.

Therefore, finding a green and efficient method for synthesizing fluoroalkyl-substituted dibenzocycloheptanones is a very challenging and research-worthy task, which provides a basis for finding new compounds with similar pharmacological activities to the natural class colchicine. offers the possibility.

Contents of the invention

The object of the present invention is to provide a method for the electrooxidative synthesis of fluoroalkyl-substituted dibenzocycloheptanones to solve the problems in the prior art, thereby green and efficient synthesis of fluoroalkyl-substituted dibenzocycloheptanones Ketones.

To achieve the above object, the present invention provides the following scheme:

The invention provides a method for electrooxidatively synthesizing fluoroalkyl-substituted dibenzocycloheptanone compounds, comprising the following steps:

Conducting an electrification reaction between o-propargyl biphenyl compounds and sodium fluoroalkylsulfinate compounds to obtain the fluoroalkyl-substituted dibenzocycloheptanone compounds;

The o-propargyl biphenyl compound has a structure as shown in formula (I):

In formula (I):

Ar is an aromatic ring;

R is H, ^an alkyl group, a halogen atom, an ester group, a nitro group, a cyano group or an alkoxy group;

R ² is an aryl group, an alkyl group or a silicon group;

The sodium fluoroalkyl sulfinate compound has a structure as shown in formula (II):

In formula (II): R is CF ₃ or CF ₂ H.

As a further preference of the present invention, the energization reaction is a constant current energization reaction of 3mA-10mA, the reaction temperature is 25-70°C, and the reaction time is 4-10h.

More preferably, the electrification reaction is a constant current electrification reaction of 4 mA, the reaction temperature is 50° C., and the reaction time is 6 h.

The synthesis process of the present invention needs to ensure a suitable reaction temperature. If the reaction temperature is too high, side reactions will increase, and if the reaction temperature is too low, the yield of the target product will be reduced.

The electrification reaction is carried out in an electrolytic cell, the anode material is carbon electrode graphite felt, and the cathode is platinum or nickel.

As a further preference of the present invention, the aromatic ring includes a benzene ring substituted by an alkyl group, an alkoxy group, an aryl group, a halogen or an ester group, furan, pyrrole or thiophene.

As a further preference of the present invention, the aromatic ring is a benzene ring substituted by an alkyl group or an alkoxy group.

As a further preference of the present invention, the R ¹ is an alkyl or alkoxy group.

As a further preference of the present invention, the R ² is an aryl group.

As a further preference of the present invention, the molar ratio of the o-propargylbiphenyl compound to the sodium fluoroalkylsulfinate compound is 1:(1-3).

As a further preference of the present invention, in the electrolytic solution used in the electrification reaction, the electrolyte is tetrabutylammonium tetrafluoroborate, lithium tert-butoxide, tetrabutylammonium iodate, tetraethylammonium perchlorate, tetraethylhexafluoro Ammonium phosphate or tetrabutylammonium perchlorate; in the electrolytic solution used in the electrification reaction, the solvents are acetonitrile, water, dichloroethane, methanol, isopropanol, ethyl acetate, N,N-dimethylformamide and tetrahydrofuran at least one of the

The electrolyte solution concentration of the electrification reaction is 0.1mol/L.

As a further preference of the present invention, the electrolyte is tetraethylamine perchlorate, and the solvent is a mixed solvent of acetonitrile and water; wherein the volume ratio of acetonitrile and water is 3:1.

The invention also provides the fluoroalkyl-substituted dibenzocycloheptanone compound synthesized by the method.

Taking the sodium difluoroalkyl sulfinate free radical source as an example, the synthesis reaction of the present invention is illustrated, and the reaction formula is as follows:

In the reaction process, the use of o-propargyl biphenyl compounds in a solvent (preferably a mixed solvent of acetonitrile and water) reacts with difluoromethyl free radical (CF ₂ H ) precursor sodium difluorosulfinate compounds , under anodic oxidation conditions in an electrolytic cell, fluoroalkyl-substituted dibenzocycloheptanones were obtained by series radical cyclization.

In the above reaction, the o-alkyne benzoylbiphenyl reacts with the sodium difluorosulfinate compound under the condition of current flow in the electrolyte and the solvent to obtain the fluoroalkyl-substituted dibenzocycloheptanone compound. The reaction mechanism is speculated as follows:

First, the difluoromethylsulfinate ion undergoes an oxidation reaction at the anode, and loses electrons to generate a difluoroalkyl radical; this radical attacks the carbonyl α-position of the biphenyl at the alkynyl carbon position to generate a thermodynamically more stable free radical A , and then the free radical A is added to the benzene ring by 7-endo-trig cycloaddition to form a new free radical B, and the new free radical B loses an electron to generate an aryl cation C, and then deprotonates to form dibenzocycloheptanones compound.

The invention discloses the following technical effects:

In the present invention, o-propargyl biphenyl compounds and sodium fluoroalkyl sulfinate compounds are used as raw materials, and the two are subjected to a constant current electrification reaction in an electrolyte solution. Under specific reaction temperature and current conditions, fluoroalkyl The sulfinate anion is oxidized to a fluoroalkyl radical, which attacks the α-position of the carbonyl of the ketynone reactant to give an alkenyl radical, which is then cycloadditioned to another benzene by 7-endo-trig The construction of a seven-membered ring is achieved at the ring, and finally deprotonated to obtain a fluoroalkyl-substituted dibenzocycloheptanone compound.

Description of drawings

In order to more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the following will briefly introduce the accompanying drawings required in the embodiments. Obviously, the accompanying drawings in the following description are only some of the present invention. Embodiments, for those of ordinary skill in the art, other drawings can also be obtained based on these drawings without any creative effort.

Fig. 1 is the ¹ H NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 1;

Fig. 2 is the ¹³ C NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 1;

Fig. 3 is the ¹⁹ F NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 1;

Fig. 4 is the ¹ H NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 2;

Fig. 5 is the ¹³ C NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 2;

Fig. 6 is the ¹⁹ F NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 2;

Fig. 7 is the ¹ H NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 3;

Fig. 8 is the ¹³ C NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 3;

Fig. 9 is the ¹⁹ F NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 3;

Figure 10 is the ¹ H NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 4;

Fig. 11 is the ¹³ C NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 4;

Fig. 12 is the ¹⁹ F NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 4;

Fig. 13 is the ¹ H NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 5;

Fig. 14 is the ¹³ C NMR spectrogram of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 5;

Fig. 15 is the ¹⁹ F NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 5.

Detailed ways

Various exemplary embodiments of the present invention will now be described in detail. The detailed description should not be considered as a limitation of the present invention, but rather as a more detailed description of certain aspects, features and embodiments of the present invention.

It should be understood that the terminology described in the present invention is only used to describe specific embodiments, and is not used to limit the present invention. In addition, regarding the numerical ranges in the present invention, it should be understood that each intermediate value between the upper limit and the lower limit of the range is also specifically disclosed. Each smaller range between any stated value or intervening value in a stated range and any other stated value or intervening value in a stated range is encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded from the range.

Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although only the preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference to disclose and describe the methods and/or materials in connection with which the documents are described. In case of conflict with any incorporated document, the contents of this specification control.

It will be apparent to those skilled in the art that various modifications and changes can be made in the specific embodiments of the present invention described herein without departing from the scope or spirit of the present invention. Other embodiments will be apparent to the skilled person from the description of the present invention. The description and examples of the invention are illustrative only.

As used herein, "comprising", "comprising", "having", "comprising" and so on are all open terms, meaning including but not limited to.

Example 1

In a reaction tube, accurately add o-propargylbiphenyl 1a (102.6 mg, 0.3 mmol, 1.0 equiv.), sodium difluoromethanesulfinate 2a (124.2 mg, 0.9 mmol, 3.0 equiv.), perchloric acid Tetraethylamine (92 mg, 0.4 mmol, 0.1 M) was finally added to the mixed solvent MeCN/H ₂ O (v/v, 3:1, 4 mL). The reaction was carried out at 50° C. for 6 h with a constant current. Transfer all solvent to a round bottom flask. Silica was added to the flask and the solvent was evaporated in vacuo. Using n-hexane/EtOAc (v/v, 3:1) as the eluent, silica gel column chromatography was used for purification to obtain the corresponding product 3a with a yield of 57%. The reaction formula is as follows:

Product NMR data: ¹ H NMR (400MHz, CDCl3) δ7.92(d, J=7.8Hz, 1H), 7.69–7.65(m,1H), 7.59–7.50(m,2H), 7.35–7.32(m ,3H),7.22(s,2H), 6.78(d,J＝2.4Hz,1H),6.41(d,J＝2.3Hz,1H),6.12(t,J＝53.6Hz,1H), 3.89(s ,3H),3.27(s,3H) ^.13 C NMR(101MHz,CDCl3)δ196.0,160.9,160.1,145.4,144.1(t,J＝9.3Hz),140.2,139.4,136.4,133.4(t,J＝6.6 Hz), 131.43, 128.9, 128.4, 128.0, 127.7, 125.3, 118.4, 112.6 (t, J=8.9Hz), 110.3, 106.9, 99.6, 55.6, 55.6. ¹⁹ F NMR (377MHz, CDCl3) δ-100.79 (d ,J＝315.9Hz), -114.66(d,J＝315.9Hz).HR–MS(ESI)m/z calc.for C ₂₄ H ₁₈ ¹⁹ F ₂ O ₃ [M+H]+: 393.1297,found: 393.1274.

FIG. 1 is the ¹ H NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 1.

Fig. 2 is the ¹³ C NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 1.

Fig. 3 is the ¹⁹ F NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 1.

Example 2

In a reaction tube, accurately add o-propargylbiphenyl 1b (126.0 mg, 0.3 mmol, 1.0 equiv.), sodium difluoromethanesulfinate 2a (124.2 mg, 0.9 mmol, 3.0 equiv.), perchloric acid Tetraethylamine (92 mg, 0.4 mmol, 0.1 M) was finally added to the mixed solvent MeCN/H ₂ O (v/v, 3:1, 4 mL). The reaction was carried out at 50° C. for 6 h with a constant current. Transfer all solvent to a round bottom flask. Silica was added to the flask and the solvent was evaporated in vacuo. Using n-hexane/EtOAc (v/v, 3:1) as the eluent, silica gel column chromatography was used for purification to obtain the corresponding product 3b with a yield of 55%. The reaction formula is as follows:

Product NMR data: ¹ H NMR (400MHz, CDCl ₃ ) δ7.88(d, J=7.9Hz, 1H), 7.67–7.63(m, 1H), 7.52(d, J=4.2Hz, 2H), 7.44 (d, J=8.5Hz, 2H), 7.07 (d, J=7.7Hz, 2H), 6.74(d, J=2.4Hz, 1H), 6.38(d, J=2.3Hz, 1H), 6.10(d , J ＝53.9Hz, 1H), 3.87(s, 3H), 3.31(s, 3H). ¹³ C NMR (101MHz, CDCl ₃ ) δ195.7, 161.1, 156.0, 145.3, 142.9(t, J＝9.2Hz ),140.3,138.5,133.7(t,J＝7.0Hz), 131.5,130.9,130.0,129.0,128.5,125.3,122.2,117.7,114.7,112.4(t,J＝8.9Hz),110.0,106.9,99.3, ₂₄ ^_ _{_} H ₁₇ ¹⁹ F ₂ O ₃ [M+H] ⁺ :471.0402,found:471.0373.

Fig. 4 is the ¹ H NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 2.

Fig. 5 is the ¹³ C NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 2.

Fig. 6 is the ¹⁹ F NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 2.

Example 3

In a reaction tube, accurately add o-propargylbiphenyl 1c (111.6 mg, 0.3 mmol, 1.0 equiv.), sodium difluoromethanesulfinate 2a (124.2 mg, 0.9 mmol, 3.0 equiv.), perchloric acid Tetraethylamine (92 mg, 0.4 mmol, 0.1 M) was finally added to the mixed solvent MeCN/H ₂ O (v/v, 3:1, 4 mL). The reaction was carried out at 50° C. for 6 h with a constant current. Transfer all solvent to a round bottom flask. Silica was added to the flask and the solvent was evaporated in vacuo. Using n-hexane/EtOAc (v/v, 3:1) as the eluent, silica gel column chromatography was used for purification to obtain the corresponding product 3c with a yield of 60%. The reaction formula is as follows:

Product NMR data: ¹ H NMR (400MHz, CDCl ₃ ) δ7.54 (d, J = 8.5Hz, 1H), 7.40 (d, J = 2.3Hz, 1H), 7.34–7.31 (m, 3H), 7.22 (s,2H),7.06(dd,J=8.5,2.4Hz,1H),6.76(d,J=2.4Hz,1H),6.40(d,J=2.4Hz,1H),6.11(t,J= 54.0 Hz,1H),3.96(s,3H),3.88(s,3H),3.26(s,3H). ¹³ C NMR(101MHz,CDCl ₃ )δ 194.8,162.0,160.9,160.2,143.8(t,J ＝9.4Hz), 140.1, 139.6139.1, 138.6, 128.4, 128.0, 127.7, 118.5, 115.2, 114.2, 113.8, 112.8(t, J＝8.4Hz), 110.5, 106.9, 99.6, 55.7, 55.6, 55.6 N. ¹⁹ F (377MHz, CDCl ₃ )δ-100.86(d, J=315.3Hz),-115.01(d, J=315.3Hz).HR–MS(ESI)m/z calc.for C ₂₅ H ₂₁ ¹⁹ F ₂ O ₄ [M+H] ⁺ :423.1403,found:423.1379.

Fig. 7 is the ¹ H NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 3.

Fig. 8 is the ¹³ C NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 3.

Fig. 9 is the ¹⁹ F NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 3.

Example 4

In a reaction tube, accurately add o-propargylbiphenyl 1a (102.6 mg, 0.3 mmol, 1.0 equiv.), sodium trifluoromethanesulfinate 2b (140.4 mg, 0.9 mmol, 3.0 equiv.), perchloric acid Tetraethylamine (92 mg, 0.4 mmol, 0.1 M) was finally added to the mixed solvent MeCN/H ₂ O (v/v, 3:1, 4 mL). The reaction was carried out at 50° C. for 6 h with a constant current. Transfer all solvent to a round bottom flask. Silica was added to the flask and the solvent was evaporated in vacuo. Using n-hexane/EtOAc (v/v, 3:1) as the eluent, silica gel column chromatography was used for purification to obtain the corresponding product 3d with a yield of 46%. The reaction formula is as follows:

Product NMR data: ¹ H NMR (600MHz, CDCl ₃ ) δ7.94(d, J=7.9Hz, 1H), 7.70(t, J=7.5Hz, 1H), 7.56(t, J=7.4Hz, 1H ),7.50(d,J=7.5Hz,1H), 7.29–7.28(m,3H),7.22(s,2H),6.76(d,J=2.1Hz,1H),6.39(d,J=2.1Hz , 1H),3.88(s,3H),3.26(s,3H). ¹³ C NMR(151MHz,CDCl ₃ )δ195.2,161.1, 160.6,145.0(q,J＝2.0Hz),140.0,139.9,136.4,131.6 ,130.08(q,J=19.2Hz), 128.9,128.3,128.0,127.8,127.2,124.9,122.5,120.7,118.5,106.9,99.8,55.6, 55.6. ¹⁹ F NMR(565MHz,CDCl ₃ )δ-52.63. HR–MS(ESI)m/z calc.for C ₂₄ H ₂₇ ¹⁹ F ₃ O ₃ [M+H] ⁺ :411.1203,found:411.1195.

FIG. 10 is the ¹ H NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 4.

Fig. 11 is the ¹³ C NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 4.

Fig. 12 is the ¹⁹ F NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 4.

Example 5

In a reaction tube, accurately add o-propargylbiphenyl 1e (124.2 mg, 0.3 mmol, 1.0 equiv.), sodium difluoromethanesulfinate 2a (106.8 mg, 0.9 mmol, 3.0 equiv.), perchloric acid Tetraethylamine (92 mg, 0.4 mmol, 0.1 M) was finally added to the mixed solvent MeCN/H ₂ O (v/v, 3:1, 4 mL). The reaction was carried out at 50° C. for 6 h with a constant current. Transfer all solvent to a round bottom flask. Silica was added to the flask and the solvent was evaporated in vacuo. Using n-hexane/EtOAc (v/v, 3:1) as the eluent, silica gel column chromatography was used for purification to obtain the corresponding product 3e with a yield of 45%. The reaction formula is as follows:

Product NMR data: ¹ H NMR (400MHz, CDCl ₃ ) δ7.87(s,1H), 7.50–7.45(m,2H),7.33–7.28(m,3H),7.18(s,2H),6.71( d,J=2.3Hz,1H), 6.40(d,J=2.2Hz,1H),6.10(t,J=53.9Hz,1H),3.88(s,3H),3.25(s,3H). ¹³ C NMR (101MHz, CDCl ₃ ) δ194.9, 161.1, 160.3, 144.4(t, J=9.3Hz), 143.7, 139.2, 138.8, 138.2, 137.4, 133.4(t, J=6.8Hz), 128.9, 128.4, 128.2, 127.8 , 126.9,118.5,112.6(t,J＝9.7Hz),110.2,106.7,100.1,55.7,55.6. ¹⁹ F NMR (377MHz,CDCl ₃ )δ-60.03(s).HR–MS(ESI)m/z calc.for C ₂₄ H ₁₈ Cl ¹⁹ F ₂ O ₃ [M+H] ⁺ :427.0907,found:427.0868.

Fig. 13 is the ¹ H NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 5.

Fig. 14 is the ¹³ C NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 5.

Fig. 15 is the ¹⁹ F NMR spectrum of the fluoroalkyl-substituted dibenzocycloheptanone compound prepared in Example 5.

The optimization process of reaction conditions is as follows:

In the reaction tube, accurately add o-propargyl biphenyl 1a (0.3mmol, 1.0equiv.), sodium difluoromethanesulfinate 2a (0.9mmol, 3.0equiv.), electrolyte 0.1M, solvent 4mL; As the anode, Pt as the cathode, through a constant current of 4mA, the reaction 6h. Transfer all solvent to a round bottom flask. Silica was added to the flask and the solvent was evaporated in vacuo. Using n-hexane/EtOAc (v/v, 3:1) as the eluent, silica gel column chromatography was used for purification to obtain product 3a, and the yield was calculated. The reaction formula is as follows:

Parameter optimization process and yield are shown in Table 1:

Table 1

In Table 1, [a] represents that the addition amount of sodium difluoromethanesulfinate 2a is 0.9mmol, 3.0equiv.; [b] represents a constant current of 3mA; [c] represents a constant current of 6mA; [d] represents GF is the anode and Ni is the cathode; [e] means Pt is the anode and Pt is the cathode; [f] means no electricity.

The above-mentioned embodiments are only to describe the preferred mode of the present invention, and are not intended to limit the scope of the present invention. Variations and improvements should fall within the scope of protection defined by the claims of the present invention.

Claims (10)

1. A method for synthesizing fluoroalkyl-substituted dibenzosuberone compounds by electrooxidation is characterized by comprising the following steps:

carrying out an electrifying reaction on an o-propargyl propionyl biphenyl compound and a fluoroalkyl sodium sulfinate compound to obtain a fluoroalkyl-substituted dibenzosuberone compound;

the o-propargyl propionyl biphenyl compound has a structure shown in a formula (I):

in formula (I):

ar is an aromatic ring;

R ¹ is H, alkyl, halogen atom, ester group, nitro, cyano or alkoxy;

R ² is aryl, alkyl or silicon;

the fluoroalkyl sodium sulfinate compound has a structure shown in a formula (II):

in formula (II): r is CF ₃ Or CF ₂ H。

2. The method according to claim 1, wherein the energization reaction is a constant current energization reaction of 3 mA-10 mA, the reaction temperature is 25-70 ℃, and the reaction time is 4-10 h.

3. The method of claim 1, wherein the aromatic ring comprises an alkyl, alkoxy, aryl, halogen, or ester substituted benzene ring, furan, pyrrole, or thiophene.

4. The method of claim 3, wherein the aromatic ring is an alkyl-or alkoxy-substituted benzene ring.

5. The method of claim 1, wherein R is ¹ Is alkyl or alkoxy.

6. The method of claim 1, wherein R is ² Is an aryl group.

7. The method according to claim 1, wherein the molar ratio of the o-propargyl biphenyl compound to the fluoroalkyl sodium sulfinate compound is 1 (1 to 3).

8. The method according to claim 1, wherein in the electrolyte solution used for the energization reaction, the electrolyte is tetrabutylammonium tetrafluoroborate, lithium tert-butoxide, tetrabutylammonium iodate, tetraethylammonium perchlorate, tetraethylammonium hexafluorophosphate, or tetrabutylammonium perchlorate; in the electrolyte solution used for the electrifying reaction, the solvent is at least one of acetonitrile, water, dichloroethane, methanol, isopropanol, ethyl acetate, N-dimethylformamide and tetrahydrofuran.

9. The method according to claim 8, wherein the electrolyte is tetraethylene perchlorate and the solvent is a mixed solvent of acetonitrile and water.

10. A fluoroalkyl substituted dibenzosuberone compound synthesized according to the method of any one of claims 1 to 9.

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