Alpha-trifluoromethoxy carbene reagent, its preparation method and application

Abstract

The application relates to the technical field of organic synthetic chemistry, in particular to an alpha-trifluoromethoxy carbene reagent and a preparation method and application thereof. The specific technical scheme is as follows: the structural general formula is as follows: wherein R is one of aryl, heteroaryl, fused ring aryl, alkenyl, alkynyl, alkyl and cycloalkyl. The application can synthesize OCF3 compounds which cannot be synthesized or are difficult to be synthesized by using existing methods, and provides a mechanism clear, operation safe and disruptive tool for the synthesis of innovative drugs and functional materials containing OCF3.

Description

Technical Field

[0001] This invention relates to the field of organic synthetic chemistry, specifically to an α-trifluoromethoxycarbene reagent, its preparation method, and its application. Background Technology

[0002] Compounds containing trifluoromethoxy (OCF3) have significant applications in pharmaceuticals, pesticides, and functional materials research. However, the relatively limited availability of preparation methods and slow development have restricted their application. Synthesizing fluorinated organic compounds using fluorinated carbene transfer reactions is a crucial synthetic strategy in fluorine chemistry, but the lack of effective methods for constructing OCF3 makes the preparation of OCF3 carbene precursors extremely challenging, resulting in the absence of reported OCF3 carbenes to date.

[0003] Existing technical solution: The structure of this reagent (chloride) is a novel compound. Although similar structures such as bromides and fluorides are known, compounds with similar structures have never been developed into OCF3 carbene reagents before. Synthetic methods for this type of compound include bromides: Angew. Chem. Int. Ed. 2017, 56, 11986-11989; fluorides: Angew. Chem. Int. Ed. 2018, 57, 13266-13270, but these methods cannot be used for the synthesis of chlorides. Summary of the Invention

[0004] To address the shortcomings of existing technologies, this invention provides an α-trifluoromethoxycarbene reagent, its preparation method, and its applications, offering a disruptive tool with a clear mechanism and safe operation for the synthesis of innovative OCF3-containing drugs and functional materials.

[0005] To achieve the above objectives, the present invention provides the following technical solution: This invention discloses an α-trifluoromethoxycarbene reagent, the general structural formula of which is as follows: In this case, R is one of aryl, heteroaryl, fused-ring aryl, alkenyl, alkynyl, alkyl, and cycloalkyl.

[0006] Preferably, when R is one of aryl, heteroaryl, fused cyclic aryl, alkenyl, alkynyl, alkyl, or cycloalkyl, R can be substituted by any one or more of alkyl, haloalkyl, aryl, substituted aryl, heteroaryl, halogen, alkoxy, aryloxy, or nitro.

[0007] Correspondingly, a method for preparing an α-trifluoromethoxycarbene reagent involves mixing an α-substituted aldehyde, CPTFI, an organic solvent, and a Lewis acid, and reacting the mixture at 25-80°C for 10 min-3 h to synthesize the α-trifluoromethoxycarbene reagent.

[0008] Preferably, the molar ratio of the α-substituted aldehyde, CPTFI, and Lewis acid is 0.05-0.4:0.1-0.6:0.01-0.15.

[0009] Preferably, the organic solvent is one of dichloromethane, 1,2-dichloroethane, chloroform, toluene, and acetonitrile.

[0010] Preferably, the Lewis acid is one of aluminum chloride, zinc chloride, tin tetrachloride, titanium tetrachloride, zirconium tetrachloride, and hafnium tetrachloride.

[0011] Correspondingly, the application of an α-trifluoromethoxy carbene reagent in the synthesis of trifluoromethoxy compounds.

[0012] Preferably, the trifluoromethoxy-containing compound is a trifluoromethoxy-substituted cyclopropane compound, a trifluoromethoxy-substituted silane compound, or a trifluoromethoxy-substituted phosphate ester compound.

[0013] Preferably, the synthesis process of the trifluoromethoxy-substituted cyclopropane compound, the trifluoromethoxy-substituted silane compound, or the trifluoromethoxy-substituted phosphate ester compound is as follows: ; Wherein, R' is one of aryl or alkyl, and R” is one of aryl, alkyl, or fluoroalkyl.

[0014] Preferably, the synthesis process of the trifluoromethoxy-substituted cyclopropane compound, the trifluoromethoxy-substituted silane compound, or the trifluoromethoxy-substituted phosphate ester compound is as follows: ; Among them, R 1 It is one of aryl, alkyl, alkoxy, arylthio, carbazole, and alkenyl, R 2 It is one of aryl, alkyl, and cycloalkyl, R 3 It is one of aryl and alkyl, R 4 For aryl, R 5 It is an alkyl group.

[0015] The present invention has the following beneficial effects: This invention provides the first preparation of an OCF3 carbene reagent, which can realize a variety of classic carbene chemical reactions for the synthesis of OCF3-containing compounds. Attached Figure Description

[0016] Figure 1 The image shows the nuclear magnetic resonance spectrum of compound 2a. Figure 2 The image shows the nuclear magnetic resonance spectrum of compound 3a. Figure 3This is the NMR spectrum of compound 5a. Detailed Implementation

[0017] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0018] Unless otherwise specified, the technical means used in the implementation examples are conventional means well known to those skilled in the art.

[0019] This invention can synthesize OCF3 compounds that are difficult or impossible to synthesize using existing methods, such as OCF3-substituted cyclopropanes, silanes, and phosphate esters. The synthetic route is as follows: .

[0020] This invention discloses an α-trifluoromethoxycarbene reagent, the general structural formula of which is as follows: In this case, R is one of aryl, heteroaryl, fused-ring aryl, alkenyl, alkynyl, alkyl, and cycloalkyl.

[0021] Furthermore, when R is one of aryl, heteroaryl, fused aryl, alkenyl, alkynyl, alkyl, or cycloalkyl, R can be substituted by any one or more of alkyl, haloalkyl, aryl, substituted aryl, heteroaryl, halogen, alkoxy, aryloxy, or nitro.

[0022] This invention discloses a method for preparing an α-trifluoromethoxycarbene reagent. The method involves mixing an α-substituted aldehyde, CPTFI, an organic solvent, and a Lewis acid, and reacting the mixture at 25-80°C for 10 min-3 h to synthesize the α-trifluoromethoxycarbene reagent. The molar ratio of the α-substituted aldehyde, CPTFI, and Lewis acid is 0.05-0.4:0.1-0.6:0.01-0.15. The organic solvent is one selected from dichloromethane, 1,2-dichloroethane, chloroform, toluene, and acetonitrile. The Lewis acid is one selected from aluminum chloride, zinc chloride, tin tetrachloride, titanium tetrachloride, zirconium tetrachloride, and hafnium tetrachloride.

[0023] This invention discloses the application of an α-trifluoromethoxy carbene reagent in the synthesis of trifluoromethoxy-containing compounds. The trifluoromethoxy-containing compounds are trifluoromethoxy-substituted cyclopropane compounds, trifluoromethoxy-substituted silane compounds, or trifluoromethoxy-substituted phosphate ester compounds.

[0024] Furthermore, the synthesis process of the trifluoromethoxy-substituted cyclopropane compounds, trifluoromethoxy-substituted silane compounds, or trifluoromethoxy-substituted phosphate ester compounds is as follows: ; Wherein, R is one of aryl, heteroaryl, fused-ring aryl, alkenyl, alkynyl, alkyl, and cycloalkyl. More preferably, when R is one of aryl, heteroaryl, fused-ring aryl, alkenyl, alkynyl, alkyl, and cycloalkyl, R can be substituted by any one or more of alkyl, haloalkyl, aryl, substituted aryl, heteroaryl, halogen, alkoxy, aryloxy, and nitro. R' is one of aryl and alkyl, and R” is one of aryl, alkyl, and fluoroalkyl.

[0025] Furthermore, the synthesis process of the trifluoromethoxy-substituted cyclopropane compounds, trifluoromethoxy-substituted silane compounds, or trifluoromethoxy-substituted phosphate ester compounds is as follows:

[0026] Among them, R 1 It is one of aryl, alkyl, alkoxy, arylthio, carbazole, and alkenyl, R 2 It is one of aryl, alkyl, and cycloalkyl, R 3 It is one of aryl and alkyl, R 4 For aryl, R 5 It is an alkyl group.

[0027] The specific synthesis process is as follows: Synthesis of trifluoromethoxy-substituted cyclopropane compounds: α-trifluoromethoxy carbene reagent, substituted olefin, base (such as KO) t The reaction is carried out with one of Bu, NaOtBu, LiOtBu, or NaH, and an organic solvent (such as one of dichloromethane, tetrahydrofuran, dioxane, or toluene) at room temperature for 15-30 hours. Separation by silica gel column chromatography yields OCF3 cyclopropane compounds. The molar ratio of α-trifluoromethoxycarbene reagent, substituted olefin, and base is 0.05-0.3 : 0.1-0.35 : 0.2-0.5.

[0028] Synthesis of trifluoromethoxy-substituted silanes: α-trifluoromethoxy carbene reagent, Si(R)3H, and a base (such as KO) are prepared. t The reaction is carried out with one of Bu, NaOtBu, LiOtBu, or NaH, and an organic solvent (such as one of dichloromethane, tetrahydrofuran, dioxane, or toluene) at room temperature for 8-24 hours. Separation by silica gel column chromatography yields α-OCF3 silane compounds. The molar ratio of α-trifluoromethoxycarbene reagent, Si(R)3H, and base is 0.05-0.3 : 0.4-1.5 : 0.2-0.5.

[0029] Synthesis of trifluoromethoxy-substituted phosphate esters: α-trifluoromethoxy carbene reagent, P(OEt)3, and a base (such as KO) are prepared. t The reaction mixture (one of Bu, NaOtBu, LiOtBu, or NaH) and an organic solvent (one of dichloromethane, tetrahydrofuran, dioxane, or toluene) is carried out at room temperature for 20-100 min, followed by silica gel column chromatography to obtain α-OCF3 phosphate ester compounds. The molar ratio of α-trifluoromethoxycarbene reagent, P(OEt)3, and base is 0.05-0.3 : 0.05-0.3 : 0.15-0.5.

[0030] To further illustrate the synthesis of the α-trifluoromethoxycarbene reagent in this invention, the following substances were selectively synthesized, but this invention is not limited to synthesizing only the following compounds.

[0031]

[0032] Example 1 Synthesis of compound 4-(chloro(trifluoromethoxy)methyl)-1,1'-biphenyl (2a) Add biphenylbenzaldehyde 1a (0.2 mmol), CPTFI (123.4 mg, 0.4 mmol, 2 times the volume), dichloromethane (1 mL), aluminum chloride (AlCl3, 6.7 mg, 0.05 mmol, 0.25 times the volume) to a flask and stir with a magnetic stir bar at 40 °C for 2 hours. After the reaction is complete, the reaction system is washed with saturated NaHCO3 aq., extracted three times with dichloromethane, the organic phases are combined, dried over anhydrous magnesium sulfate (MgSO4), filtered, the filtrate is collected and concentrated, and the crude product is separated by triethylamine-treated silica gel column chromatography (eluent: petroleum ether) to obtain a yellow solid 2a (51.5 mg, 90%).

[0033] The reaction equation is:

[0034] The nuclear magnetic resonance spectrum of the obtained product 2a is as follows: Figure 1 (A is the proton spectrum, B is the carbon spectrum, and C is the fluorine spectrum) As shown, the nuclear magnetic resonance data are: 1 H NMR (500 MHz, CDCl3) δ 7.68 (d, J = 8.0 Hz, 2H), 7.62 (d, J = 8.0 Hz, 4H), 7.50 (t, J = 7.8 Hz, 2H), 7.42 (t, J = 7.5 Hz (1H), 6.95 (s, 1H).13 C NMR (151 MHz, CDCl3) δ 143.2, 140.0, 135.6, 128.9, 127.9, 127.5, 127.2, 126.2,121.0 (q, J = 260.9 Hz), 86.5 (q, J = 3.9 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.57(s, 3F).GC-MS (EI, m / z, %): C 14 H 10 ClF3O, 286.00 (M + . 13), 251.01 (100), 181.05 (18). The synthesis methods for the remaining compounds 2b-2z, 2aa, and 2ab are the same as in Example 1, only requiring the replacement of the corresponding aldehydes. The structural formulas and NMR data of the synthesized compounds 2b-2z, 2aa, and 2ab are as follows: 1-(chloro(trifluoromethoxy)methyl)-4-methylbenzene (2b):

[0035] The NMR data of the obtained product 2b are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.38 (d, J = 7.8 Hz, 2H), 7.21 (d, J = 7.8 Hz, 2H), 6.81 (s, 1H), 2.36 (s, 3H). 13 C NMR (151 MHz, CDCl3) δ 140.4, 133.9,129.4, 125.7, 120.9 (q, J = 260.8 Hz), 86.7 (q, J = 4.1 Hz), 21.2. 19 F NMR (565MHz, CDCl3) δ -59.39 (s, 3F).GC-MS (EI, m / z, %): C9H8ClF3O, 223.97 (M + 3), 189.00 (100), 123.08 (22). 1-(chloro(trifluoromethoxy)methyl)-4-isopropylbenzene (2c):

[0036] The NMR data of the obtained product 2c are as follows: 1 H NMR (500 MHz, CDCl3) δ 7.45 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 8.5 Hz, 2H), 6.85 (s, 1H), 3.00 – 2.91 (m, 1H), 1.27 (d, J = 7.0 Hz, 6H). 13 C NMR (151MHz, CDCl3) δ 151.3, 134.2, 126.9, 125.8, 121.0 (q, J = 260.8 Hz), 86.7 (q, J = (4.0 Hz), 34.0, 23.8. 19 F NMR (565 MHz, CDCl3) δ -59.51 (s, 3F). 1-(tert-butyl)-4-(chloro(trifluoromethoxy)methyl)benzene (2d):

[0037] The 2-day NMR data of the obtained product are as follows: 1 H NMR (500 MHz, CDCl3) δ 7.48 (d, J = 2.0 Hz, 4H), 6.88 (s, 1H), 1.36 (s, 9H). 13 C NMR (151 MHz, CDCl3) δ 153.6, 133.9, 125.8, 125.5, 121.0 (q, J = 260.9 Hz), 86.7 (q, J = 4.2 Hz), 34.8, 31.2. 19 F NMR (565 MHz, CDCl3) δ -59.49(s, 3F). 1-(chloro(trifluoromethoxy)methyl)-4-phenoxybenzene (2e):

[0038] The NMR data of the obtained product 2e are as follows: 1 H NMR (500 MHz, CDCl3) δ 7.48 (d,J = 8.5 Hz, 2H), 7.39 (t, J = 8.0 Hz, 2H), 7.18 (t, J = 7.5 Hz, 1H), 7.07-7.02 (m, 4H), 6.85 (s, 1H). 13 C NMR (151MHz, CDCl3) δ 159.2, 156.1, 131.2, 130.0, 127.5, 124.2, 120.9 (q, J = 261.2Hz), 119.7, 118.2, 86.4 (q, J = 4.2 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.45 (s,3F). 1-Chloro-4-(chloro(trifluoromethoxy)methyl)benzene (2f):

[0039] The nuclear magnetic resonance data of the obtained product 2f are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.47 (d, J = 9.0 Hz, 2H), 7.42 (d, J = 8.4 Hz (2H), 6.85 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 136.3, 135.2, 129.1, 127.2, 120.9(q, J = 261.3Hz), 85.7 (q, J = 3.9 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.46 (s,3F). 1-Bromo-4-(chloro(trifluoromethoxy)methyl)benzene (2g):

[0040] The NMR data of 2g of the obtained product are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.58 (d, J = 8.4 Hz, 2H), 7.40 (d, J = 8.4 Hz (2H), 6.82 (s, 1H). 13C NMR (151 MHz, CDCl3) δ 135.7, 132.1, 127.4, 124.5, 120.9(q, J = 261.4 Hz), 85.8 (q, J = 4.1 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.55 (s,3F). 1-(chloro(trifluoromethoxy)methyl)-4-iodobenzene (2h):

[0041] The NMR data of the obtained product after 2 hours are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.78 (d, J = 8.4 Hz, 2H), 7.25 (d, J = 8.4 Hz (2H), 6.80 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 138.0, 136.3, 127.4, 120.9 (q, J = 261.3 Hz), 96.4, 85.9 (q, J = 3.8 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.53 (s,3F). 1-(chloro(trifluoromethoxy)methyl)-4-(trifluoromethyl)benzene (2i):

[0042] The nuclear magnetic resonance data of the obtained product 2i are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.72 (d, J = 7.8 Hz, 2H), 7.66 (d, J = 8.4 Hz (2H), 6.90 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 140.2, 132.4 (q, J = 3.3 Hz), 126.3, 125.96 (q, J = 3.6 Hz), 123.6 (q, J = 272.9 Hz), 120.9 (q, J =261.4 Hz), 85.4 (q, J = 3.9 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.61 (s, 3F), -63.01 (s, 3F). 1-(chloro(trifluoromethoxy)methyl)-4-nitrobenzene (2j):

[0043] The NMR data of the obtained product 2j are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.31 (d, J = 8.4 Hz, 2H), 7.72 (d, J = 8.4 Hz (2H), 6.94 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 148.8, 142.7, 127.0, 124.2, 120.8(q, J = 262.0 Hz), 84.7 (q, J = 4.2 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.58 (s,3F). 1-(chloro(trifluoromethoxy)methyl)-3-methylbenzene (2k):

[0044] The NMR data of the obtained product at 2k are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.42 – 7.32 (m, 3H), 7.22-7.20 (m, 1H), 6.80 (s, 1H), 2.37 (s, 3H). 13 C NMR (151 MHz, CDCl3) δ 138.7, 136.7, 131.0, 128.7,126.3, 122.8, 121.0 (q, J = 261.1 Hz), 86.7 (q, J = 3.9 Hz), 21.3. 19 F NMR (565MHz, CDCl3) δ -59.48 (s, 3F). 1-(chloro(trifluoromethoxy)methyl)-3-methoxybenzene (2l):

[0045] The nuclear magnetic resonance data of the obtained product 2l are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.35 (t, J = 7.8 Hz, 1H), 7.10-7.07 (m, 2H), 6.97 (ddd, J = 8.4, 2.7, 0.9 Hz, 1H), 6.83 (s, 1H), 3.85 (s, 3H). 13 C NMR (151MHz, CDCl3) δ 159.8, 138.1, 129.9, 120.9 (q, J = 261.0 Hz), 117.9, 115.9,111.2, 86.4 (q, J = 4.0 Hz), 55.4. 19 F NMR (565 MHz, CDCl3) δ -59.52 (s, 3F). 1-(chloro(trifluoromethoxy)methyl)-3-iodobenzene (2m):

[0046] The NMR data of the obtained product at 2m are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.87 (s, 1H), 7.77 (d, J = 7.8 Hz, 1H), 7.49 (d, J = 7.8 Hz, 1H), 7.18 (t, J = 7.8 Hz (1H), 6.79 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 139.3, 138.6, 134.7, 130.5, 125.0, 120.8 (q, J = 261.5 Hz), 94.1,85.2 (q, J = 4.0 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.50 (s, 3F). 2-(chloro(trifluoromethoxy)methyl)-1,1'-biphenyl(2n):

[0047] The nuclear magnetic resonance data of the obtained product 2n are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.85 (d, J = 7.8 Hz, 1H), 7.51-7.41 (m, 5H),7.33 (d, J = 7.8 Hz, 2H), 7.27 (dd, J = 7.5, 1.5 Hz, 1H), 6.80 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 139.4, 138.6, 134.8, 129.97, 129.90, 129.0, 128.6, 128.4,128.1, 126.8, 120.7 (q, J = 261.1 Hz), 84.4 (q, J = 3.9 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.27 (s, 3F). 1-Bromo-2-(chloro(trifluoromethoxy)methyl)benzene (2o):

[0048] The NMR data of the obtained product 2o are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.73 (dd, J = 8.1, 1.5 Hz, 1H), 7.55 (dd, J = 7.8, 1.2 Hz, 1H), 7.39 (td, J = 7.5, 1.5 Hz, 1H), 7.24 (td, J = 7.8, 1.8 Hz, 1H), 7.19 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 136.1, 132.9, 131.5, 128.2,127.7, 120.8 (q, J = 261.5 Hz), 120.6, 85.4 (q, J = 3.9 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.27 (s, 3F). 1,3-Di-tert-butyl-5-(chloro(trifluoromethoxy)methyl)benzene (2p):

[0049] The NMR data of the obtained product 2p are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.50 (t, J = 1.5 Hz, 1H), 7.34 (d, J = 1.8 Hz, 2H), 6.85 (s, 1H), 1.34 (s, 18H). 13 C NMR (151 MHz, CDCl3) δ 151.6, 136.0,124.5, 121.0 (q, J = 260.8 Hz), 120.0, 87.5 (q, J = (4.0 Hz), 35.0, 31.4. 19 F NMR (565 MHz, CDCl3) δ -59.29 (s, 3F). 1-Bromo-4-(chloro(trifluoromethoxy)methyl)-2-methoxybenzene (2q):

[0050] The NMR data of the obtained product 2q are as follows: 1 H NMR (500 MHz, CDCl3) δ 7.72 (d, J = 2 Hz, 1H), 7.42 (dd, J = 8.5, 2.5Hz, 1H), 6.91 (d, J = 8.5 Hz, 1H), 6.79 (s, 1H), 3.92 (s, 3H). 13 C NMR (151 MHz, CDCl3) δ 157.2, 130.9, 130.1, 126.2, 120.8 (q, J = 261.2 Hz), 111.9, 111.5,85.5 (q, J = 4.0 Hz), 56.4. 19 F NMR (565 MHz, CDCl3) δ -59.48 (s, 3F). 2-(chloro(trifluoromethoxy)methyl)-1,3,5-trimethylbenzene (2r):

[0051] The nuclear magnetic resonance data of the obtained product 2r are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.18 (s, 1H), 7.87 (s, 2H), 2.46 (s, 6H), 2.27 (s, 3H). 13 C NMR (151 MHz, CDCl3) δ 139.9, 135.9, 132.8, 130.0, 121.0 (q, J = 260.5 Hz), 84.3 (q, J = (4.2 Hz), 20.9, 19.9. 19 F NMR (565 MHz, CDCl3) δ -59.92(s, 3F). 2-(chloro(trifluoromethoxy)methyl)naphthalene(2s):

[0052] The nuclear magnetic resonance data of the obtained product 2s are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.98 (s, 1H), 7.93 (d, J = 8.4 Hz, 1H), 7.90(td, J = 7.2, 3.0 Hz, 2H), 7.66 (dd, J = 8.4, 1.8 Hz, 1H), 7.61 – 7.55 (m, 2H), 7.07 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 133.9 (d, J = 3.6 Hz), 132.5, 129.1,128.5, 127.8, 127.4, 126.9, 125.2, 122.7, 121.1 (q, J = 261.0 Hz), 86.9 (q, J = 4.1 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.36 (s, 3F). (3R,5R,7R)-1-[5-[6-(chloro(trifluoromethoxy)methyl)naphth-2-yl]-2-methoxyphenyl]adamantane (2t):

[0053] The NMR data of the obtained product 2t are as follows: 1 H NMR (600 MHz, CDCl3) δ 8.00 (s, 1H), 7.95 (s, 1H), 7.94 (s, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.79 (dd, J = 8.4, 1.8 Hz, 1H), 7.61 (dd, J = 8.4, 1.8Hz, 1H), 7.59 (d, J = 1.8 Hz, 1H), 7.52 (s, 1H), 7.02 (s, 1H), 6.98 (s, 1H), 3.89 (s, 3H), 2.18 (s, 6H), 2.10 (s, 3H), 1.80 (s, 6H). 13 C NMR (151 MHz, CDCl3) δ 158.9, 140.6, 139.0, 134.3, 133.4, 132.6, 131.3, 129.3, 128.9,126.8, 125.9, 125.7, 125.04, 124.8, 123.1, 121.1 (q, J = 260.9 Hz), 112.1,87.0 (q, J = 3.8 Hz), 55.2, 40.6, 37.23, 37.15, 29.1. 19 F NMR (565 MHz, CDCl3) δ-59.35 (s, 3F).HRMS (ESI) m / z: calc'd for C 29 H 29 ClF3O2[M+H] + 501.1803, found 501.1795. 2-(chloro(trifluoromethoxy)methyl)thiophene (2u):

[0054] The nuclear magnetic resonance data of the obtained product 2u are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.46 (d, J = 3.0 Hz, 1H), 7.35-7.33 (m, 1H),7.18 (d, J = 5.4 Hz (1H), 6.93 (s, 1H). 13C NMR (151 MHz, CDCl3) δ 137.6, 127.3,125.2, 124.1, 120.9 (q, J = 262.3 Hz), 82.7 (q, J = 4.1 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.41 (s, 3F). GC-MS (EI, m / z, %): C6H4ClF3OS, 215.92 (M + 7), 180.96(100), 115.01 (20). 2-(chloro(trifluoromethoxy)methyl)-5-nitrofuran (2v):

[0055] The NMR data of the obtained product 2v are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.31 (d, J = 4.0 Hz, 1H), 6.87-6.86 (m, 2H). 13 C NMR (151 MHz, CDCl3) δ 152.2, 149.3, 120.7 (q, J = 263.2 Hz), 112.5,111.4, 77.8 (q, J = 4.5 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.77 (s, 3F).GC-MS(EI, m / z, %): C6H3ClF3NO4, 244.96 (M + 5), 209.94 (100), 136.01 (16). (E)-(3-chloro-3-(trifluoromethoxy)prop-1-en-1-yl)benzene (2w):

[0056] The NMR data of the obtained product 2w are as follows: 1 H NMR (500 MHz, CDCl3) δ 7.42 (d, J = 7.0 Hz, 2H), 7.38 - 7.35 (m,3H), 6.80 (d, J = 16.0 Hz, 1H), 6.50 (d,J = 6.0 Hz, 1H), 6.32 (dd, J = 16.0, 6.3 Hz, 1H). 13 C NMR (151 MHz, CDCl3) δ 134.3, 133.8, 129.3, 128.8, 127.2,123.6, 120.9 (q, J = 260.9 Hz), 86.2 (q, J = 4.1 Hz). 19 F NMR (565 MHz, CDCl3) δ-59.34 (s, 3F).GC-MS (EI, m / z, %): C 10 H8ClF3O, 236.02 (M + 5), 201.02 (85), 115.06 (100). (E)-1-Chloro-4-(3-Chloro-3-(trifluoromethoxy)prop-1-en-1-yl)benzene (2x):

[0057] The NMR data of the obtained product 2x are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.34 (d, J = 1.2 Hz, 4H), 6.76 (dd, J = 15.6, 1.2 Hz, 1H), 6.50 (dd, J = 6.0, 1.2 Hz, 1H), 6.30 (dd, J = 16.2, 6.0 Hz, 1H). 13 CNMR (151 MHz, CDCl3) δ 135.1, 132.8, 132.5, 129.0, 128.4, 124.2, 120.9 (q, J = 261.1 Hz), 85.9 (q, J = 4.1 Hz 19 F NMR (565 MHz, CDCl3) δ -59.38 (s, 3F).GC-MS (EI, m / z, %):C 10 H7Cl2F3O, 269.93 (M + 5), 234.98 (100), 149.02 (30). (3-Chloro-3-(trifluoromethoxy)prop-1-yn-1-yl)benzene (2y):

[0058] The nuclear magnetic resonance data of the obtained product 2y are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.52 (d, J = 7.2 Hz, 2H), 7.43 (t, J = 7.5 Hz, 1H), 7.37 (t, J = 7.5 Hz (2H), 6.65 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 132.0,130.0, 128.5, 120.7 (q, J = 262.6 Hz), 120.1, 90.3, 80.7, 73.7 (q, J = 4.9 Hz). 19 F NMR (565 MHz, CDCl3) δ -59.33 (s, 3F).GC-MS (EI, m / z, %): C 10 H6ClF3O, 233.94 (M + 14), 199.00 (100), 151.01 (35). (3-Chloro-3-(trifluoromethoxy)propyl)benzene (2z):

[0059] The nuclear magnetic resonance data of the obtained product 2z are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.31 (m, 2H), 7.22 (t, J = 7.2 Hz, 1H), 7.17 (d, J = 7.2 Hz, 2H), 5.82 (t, J = 6.0 Hz, 1H), 2.85-2.75 (m, 2H), 2.43-2.30 (m, 2H). 13 C NMR (151 MHz, CDCl3) δ 139.2, 128.7, 128.3, 126.5, 121.0 (q, J = 260.2Hz), 87.1 (q, J =3.8 Hz), 40.6, 30.6. 19 F NMR (565 MHz, CDCl3) δ -59.51 (s,3F).GC-MS (EI, m / z, %): C 10 H 10 ClF3O, 237.96 (M + . 33), 117.08 (50), 91.00 (100). (chloro(trifluoromethoxy)methyl)cyclopentane (2aa):

[0060] The nuclear magnetic resonance data of the obtained product 2aa are as follows: 13 C NMR (151 MHz, CD2Cl2) δ 121.1 (q, J = 259.3 Hz), 91.6 (q, J = 3.5Hz), 47.6, 28.6, 28.3, 25.6, 25.5. 19 F NMR (565 MHz, CD2Cl2) δ -59.81 (s, 3F). 1-Chloro-2,2-dimethyl-1-(trifluoromethoxy)propane (2ab):

[0061] The NMR data of the obtained product 2ab are as follows: 19 F NMR (565 MHz, CDCl3) δ -59.97 (s, 3F). Example 2 Synthesis of trifluoromethoxy-substituted cyclopropane compounds Compound 2 was reacted with various alkenes to generate cyclopropane 3, specifically as follows: alkene (alkene, 0.1 mmol), compound 2 (0.15 mmol, 1.5 times the amount), and KO were added sequentially to a 5 mL reaction flask (with a built-in magnetic stir bar). t Bu (0.3 mmol, 3 times the volume) and dichloromethane (1.0 mL). After stirring at 25 °C for 20 hours, the reaction was quenched with an appropriate amount of dilute hydrochloric acid. After three extractions with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated by silica gel column chromatography using petroleum ether as the eluent to obtain cyclopropane product 3.

[0062] The reaction equation is as follows: .

[0063] The specific compounds synthesized are as follows: The synthesis of compound 4,4''-(1-(trifluoromethoxy)cyclopropane-1,2-diyl)bis-1,1'-biphenyl (3a) is as follows: Add bistyrene (0.1 mmol), compound 2a (0.15 mmol, 1.5 times the volume), and KO to a 5 mL reaction flask (with built-in magnetic stirrer) in sequence. t Bu (0.3 mmol, 3 equiv.) and dichloromethane (1.0 mL). After stirring at 25 °C for 20 hours, the reaction was quenched with an appropriate amount of dilute hydrochloric acid. After three extractions with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated by silica gel column chromatography using petroleum ether as eluent to obtain a white solid 4,4''-(1-(trifluoromethoxy)cyclopropane-1,2-diyl)di-1,1'-biphenyl (3a) (42.6 mg, 99%).

[0064] The reaction equation is:

[0065] The NMR spectrum of compound 3a is as follows: Figure 2 (A is the proton spectrum, B is the carbon spectrum, and C is the fluorine spectrum) As shown, the nuclear magnetic resonance data are: 1 H NMR (600 MHz, CDCl3) major: δ = 7.55 (d, J = 7.8 Hz, 2H), 7.52 (d, J = 7.8 Hz, 2H), 7.48 (d, J = 8.4 Hz, 2H), 7.43-7.30 (m, 10H), 6.99 (dd, J = 8.0Hz, 2H), 3.04 (dd, J = 11.0, 8.0 Hz, 1H), 2.14 (dd, J = 10.8, 7.3 Hz, 1H), 1.93(t, J = 7.5 Hz, 1H), minor: δ = 7.67-7.63 (m, 8H), 7.54 (d, J = 7.8 Hz, 2H), 7.49 (q, J = 7.2 Hz, 4H), 7.41-7.37 (m, 4H), 2.46 (dd, J = 10.2, 8.4 Hz, 1H), 2.20 (t,J = 8.1 Hz, 1H), 2.11 (dd, J = 10.2, 7.2 Hz, 1H). 13 C NMR (151 MHz, CDCl3)major: δ = 141.1. 140.5, 140.3, 139.2, 130.1, 128.8, 128.7, 128.5, 127.5,127.2, 127.1, 126.9, 126.8, 126.7, 122.4 (q, J = 259.1 Hz), 68.4 (d, J = 1.8Hz), 30.0, 17.0; minor: δ 141.0, 140.8, 140.5, 139.9, 138.6, 133.8, 128.9,128.8, 127.6, 127.4, 127.3, 127.2, 127.1, 127.0, 126.6, 122.6 (q, J = 259.0Hz), 66.2, 32.5, 16.8. 19 F NMR (565 MHz, CDCl3) major: δ = -54.26 (s, 3F), minor: -54.42 (s, 3F).GC-MS (EI, m / z , %): C 28 H 21 F3O, 430.13 (M + , 100), 345.13(74), 191.09 (74). The synthesis methods for the remaining compounds 3b-3z and 3aa-3aq are the same as those for compound 3a in Example 2, only requiring the replacement of the corresponding compound 2 and alkene. The structural formulas and NMR data of the synthesized compounds 3b-3z and 3aa-3aq are as follows: 4-[2-(p-Tolyl)-1-(Trifluoromethoxy)cyclopropyl]-1,1'-Biphenyl (3b):

[0066] The NMR data for compound 3b are as follows: 1 H NMR (500 MHz, CDCl3) major: δ= 7.55 (d, J = 7.5 Hz, 2H), 7.45 (d, J =8.0 Hz, 2H), 7.42 (t, J = 7.5 Hz, 2H), 7.35-7.31 (m, 3H), 6.93 (d, J = 8.0 Hz,2H), 6.81 (d, J = 8.0 Hz, 2H), 2.96 (dd, J = 11.0, 8.0 Hz, 1H), 2.23 (s, 3H),2.07 (dd, J = 10.8, 7.3 Hz, 1H), 1.86 (t, J = 7.8 Hz, 1H), minor: 7.61-7.59 (m,4H), 7.48-7.42 (m, 4H), 7.35 (td, J = 7.2, 1.8 Hz, 1H), 7.19-7.15 (m, 4H),2.36-2.33 (m, 4H), 2.09 (t, J = 8.1 Hz, 1H), 1.99 (dd, J = 10.2, 7.8 Hz, 1H). 13 CNMR (151 MHz, CDCl3) major: δ = 140.8, 140.3, 136.0, 133.3, 132.4, 129.9,128.72, 128.70, 127.9, 127.4, 127.0, 126.6, 122.3 (q, J = 258.8 Hz), 68.1 (d, J = 1.8Hz), 30.0, 20.9, 16.6, minor: 140.8. 140.5, 138.8, 136.6, 131.6, 129.0,128.9, 128.6, 128.4, 127.6, 127.4, 127.2, 127.0, 126.5, 122.6 (q, J = 259.0Hz), 66.0, 32.4, 21.2, 16.5. 19 F NMR (565 MHz, CDCl3) major: δ = -54.27 (s,3F), minor: -54.39 (s, 3F).GC-MS (EI, m / z , %): C 23 H 19 F3O, 368.06 (M+ , 100),283.11 (90), 191.06 (50). 4-[2-(4-tert-butylphenyl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3c):

[0067] The NMR data for compound 3c are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.55 (d, J = 8.4 Hz, 2H), 7.46 (d, J = 7.8 Hz, 2H), 7.42 (t, J = 7.5 Hz, 3H), 7.34 (d, J = 8.7 Hz, 3H), 7.16 (d, J =8.4 Hz, 2H), 6.85 (d, J = 8.4 Hz, 2H), 2.97 (dd, J = 10.8, 7.2 Hz, 1H), 2.08 (dd, J = 10.8, 7.2 Hz, 1H), 1.85 (t, J = 7.8 Hz (1H), 1.24 (s, 9H). 13 C NMR (151MHz, CDCl3) major: δ = 149.4, 140.9, 140.4, 133.4, 132.6, 130.0, 128.7,127.7, 127.4, 127.0, 126.6, 124.9, 122.3 ( J = 258.8 Hz), 68.2 (d, J = 2.3 Hz),34.3, 31.2, 29.9, 16.9. 19 F NMR (565 MHz, CDCl3) major: δ = -54.27 (s, 3F), minor: -54.47 (s, 3F).GC-MS (EI, m / z, %): C 26 H 25 F3O, 410.09 (M + . 100), 353.05(50), 191.09 (42). 4-[2-(4-methoxyphenyl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3d):

[0068] The NMR data for compound 3d are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.52–7.50 (m, 2H), 7.42 (d, J = 8.4Hz, 2H), 7.38 (t, J = 7.8 Hz, 2H), 7.31–7.26 (m, 3H), 6.82 (d, J = 8.4 Hz, 2H), 6.63 (d, J = 9.0 Hz, 2H), 3.66 (s, 3H), 2.91 (dd, J = 11.4, 8.1 Hz, 1H), 2.02(dd, J = 10.8, 7.2 Hz, 1H), 1.79 (t, J = 7.8 Hz, 1H); minor: 7.61–7.58 (m, 4H),7.47–7.43 (m, 4H), 7.34 (t, J = 7.8 Hz, 1H), 7.21 (d, J = 8.4 Hz, 2H), 6.89 (d, J = 8.4 Hz, 2H), 3.80 (s, 3H), 2.33 (dd, J = 10.2, 8.4 Hz, 1H), 2.05 (t, J = 7.8 Hz, 1H), 1.98 (dd, J = 9.9, 7.8 Hz, 1H). 13 C NMR (126 MHz, CDCl3) major: δ =158.2, 140.8, 140.3, 133.4, 129.8, 129.1, 128.7, 127.4, 127.0, 126.6, 122.3(q, J = 260.1 Hz), 113.5, 68.0 (d, J= 1.4 Hz), 55.0, 29.6, 16.5; minor: 158.6,140.7, 140.4, 138.7, 133.4, 129.5, 128.8, 127.5, 127.3, 127.1, 126.4, 122.5(q, J = 259.3 Hz), 113.7, 65.8 (d, J = (1.5 Hz), 55.2, 32.0, 28.2. 19 F NMR (565MHz, CDCl3) major: δ = -54.25 (s, 3F), minor: -54.40 (s, 3F).GC-MS (EI, m / z,%): C 23 H 19 F3O2, 384.05 (M + . 67), 299.08 (100), 191.07 (35). 4-[2-Phenylacetyl-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3e):

[0069] The NMR data for compound 3e are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.53 (d, J = 7.2 Hz, 2H), 7.44 (d, J = 8.4 Hz, 2H), 7.40 (t, J = 7.8 Hz, 2H), 7.34-7.29 (m, 3H), 7.13-7.07 (m, 3H), 6.92 (d, J = 7.2 Hz, 2H), 6.93 (d, J = 7.2 Hz, 2H), 3.00 (dd, J = 10.8, 8.4 Hz, 1H), 2.09 (dd, J = 10.8, 7.2 Hz, 1H), 1.90 (t, J = 7.8 Hz, 1H), minor: 7.61 (t, J = 7.8 Hz, 4H), 7.48 (d, J = 7.8 Hz, 2H), 7.44 (t, J= 7.5 Hz, 2H), 7.36 (t, J =7.5 Hz, 3H), 7.31-7.27 (m, 3H), 2.39 (t, J = 9.0 Hz, 1H), 2.12 (t, J = 8.1 Hz, 1H), 2.02 (dd, J = 10.2, 7.8 Hz, 1H). 13 C NMR (126 MHz, CDCl3) major: δ = 141.0,140.3, 135.6, 133.2, 129.9, 128.7, 128.1, 128.0, 127.4, 127.0, 126.6, 126.5,122.3 (q, J = 258.9 Hz), 68.2, 30.3, 16.6, minor: 140.9. 140.5, 138.6, 134.7,128.9, 128.6, 128.3, 127.6, 127.4, 127.2, 127.0, 126.6, 122.5 (q, J = 258.8Hz), 68.4 (d, J = 1.5 Hz), 32.6, 16.5. 19 F NMR (565 MHz, CDCl3) major: δ = -54.30 (s, 3F), minor: -54.49 (s, 3F).GC-MS (EI, m / z , %): C 22 H 17 F3O, 354.10 (M + ,100), 269.11 (55), 191.07 (40). 4-[2-(4-fluorophenyl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3f):

[0070] The NMR data for compound 3f are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.54 (d, J = 7.5 Hz, 2H), 7.45 (d, J = 8.0 Hz, 2H), 7.42 (t,J = 7.5 Hz, 2H), 7.34 (t, J = 7.5 Hz, 1H), 7.29 (d, J = 8.5 Hz, 2H), 6.89-6.86 (m, 2H), 6.83-6.79 (m, 2H), 2.96 (dd, J = 10.5, 8.0 Hz, 1H), 2.09 (dd, J = 10.5, 7.5 Hz, 1H), 1.86 (t, J = 7.5 Hz, 1H). 13 C NMR (151 MHz, CDCl3) major: δ = 162.3, 160.7, 141.1, 140.2, 133.0, 131.3 (d, J = 3.3 Hz), 129.8, 129.6 (d, J = 8.0 Hz), 128.7, 127.5, 127.0, 126.7, 122.3 (q, J = 258.8Hz), 115.0, 114.9, 67.9, 29.6, 16.6. 19 F NMR (565 MHz, CDCl3) major: δ= -54.41(s, 3F), -116.01--116.06 (m, 1F), minor: -54.54 (s, 3F), -115.81--115.86 (m,1F).GC-MS (EI, m / z, %): C 22 H 16 F4O, 372.00 (M + . 100), 287.06 (73), 109.05 (57). 4-[2-(4-chlorophenyl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3g):

[0071] The NMR data for compound 3g are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.56 (d, J = 8.4 Hz, 2H), 7.47 (d, J = 8.4 Hz, 2H), 7.43 (t, J= 7.5 Hz, 2H), 7.35 (t, J = 7.2 Hz, 1H), 7.31 (d, J =8.4 Hz, 2H), 7.10 (d, J = 8.4 Hz, 2H), 6.85 (d, J = 8.4 Hz, 2H), 2.95 (dd, J =10.8, 8.4 Hz, 1H), 2.11 (d, J = 10.8, 7.2 Hz, 1H), 1.87 (t, J = 7.8 Hz, 1H). 13 CNMR (151 MHz, CDCl3) major: δ = 141.2, 140.1, 134.2, 132.7, 132.3, 129.9,129.3, 128.7, 128.2, 127.5, 127.0, 126.8, 122.3 (q, J = 259.0 Hz), 68.1 (d, J = 2.3 Hz), 29.7, 16.8; minor: 141.1, 140.4, 138.2, 133.3, 132.8, 129.8, 128.9,128.4, 127.6, 127.4, 127.1, 126.6, 122.4 (q, J = 259.0 Hz), 65.9 (d, J = 2.1Hz), 31.9, 16.7. 19 F NMR (565 MHz, CDCl3) δ = -54.43 (s, 3F), -54.57 (s, 3F).GC-MS (EI, m / z , %): C 22 H 16 ClF3O, 388.09 (M + , 100), 303.05 (62), 191.06 (33). 4-[2-(4-bromophenyl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3h):

[0072] The NMR data of compound 3h are as follows: 1H NMR (600 MHz, CDCl3) major: δ = 7.55 (d, J = 8.4, 1.2 Hz, 2H), 7.55(dd, J = 8.4, 1.2 Hz, 2H), 7.42 (t, J = 7.5 Hz, 2H), 7.35-7.32 (m, 1H), 7.28 (d, J = 8.4 Hz, 2H), 7.23 (dt, J =9.0, 2.1 Hz, 2H), 6.77 (d, J = 8.4 Hz, 2H), 2.91(dd, J = 10.8, 8.4 Hz, 1H), 2.09 (dd, J = 10.8, 7.2 Hz, 1H), 1.85 (t, J = 7.8 Hz,1H), minor: 7.64 (dd, J = 10.5, 8.1 Hz, 4H), 7.52-7.47 (m, 6H), 7.40 (t, J = 7.5Hz, 1H), 7.20 (d, J = 8.4 Hz, 1H), 2.38 (dd, J = 10.2, 7.8 Hz, 1H), 2.10 (t, J =8.1 Hz, 1H), 2.06 (dd, J = 10.2, 7.8 Hz, 1H). 13 C NMR (151 MHz, CDCl3) major: δ =141.3, 140.2, 134.8, 132.7, 131.2, 129.9, 129.7, 128.8, 127.7, 127.0, 126.9,122.2 (q, J = 259.3 Hz), 68.4 (d, J = 2.0 Hz), 29.8, 16.8. minor: 141.1, 140.4,138.2, 133.9, 131.4, 130.2, 128.9, 127.6, 127.4, 127.1, 126.7, 122.4 (q, J =259.0 Hz), 121.0, 65.9 (d,J = 1.8 Hz), 31.9, 16.7. 19 F NMR (565 MHz, CDCl3)major: δ = -54.44 (s, 3F), minor: -54.52 (s, 3F).GC-MS (EI, m / z , %):C 22 H 16 BrF3O, 432.00 (M + , 95), 268.09 (100), 152.06 (40). 4-[1-(trifluoromethoxy)-2-(4-trifluoromethylphenyl)cyclopropyl]-1,1'-biphenyl (3i):

[0073] The NMR data for compound 3i are as follows: 1 H NMR (500 MHz, CDCl3) mixture of diastereomers: δ = 7.63-6.96 (m,13H),2.98 (dd, J = 10.8, 7.8 Hz, 1H), 2.43 (dd, J = 10.2, 7.8 Hz, 1H), 2.16-2.12 (m, 1H), 2.08 (dd, J = 10.2, 7.8 Hz, 1H), 1.91 (t, J = 7.8 Hz, 1H). 13 C NMR (151 MHz, CDCl3) major: δ = 141.5, 140.1, 140.0, 132.4, 130.1, 128.8, 128.3,127.6, 127.0, 126.9, 124.9 (q, J = 3.8 Hz), 122.3 (q, J = 273.6 Hz), 122.2 (q, J = 259.2 Hz), 68.4 (d, J = (1.4 Hz), 30.0, 17.2. 19F NMR (565 MHz, CDCl3) major: δ= -54.49 (s, 3F), -62.46 (s, 3F), minor: -54.66 (s, 3F), -62.38 (s, 3F).GC-MS(EI, m / z, %): C 23 H 16 F6O, 422.03 (M + 100), 337.04 (45), 158.99 (45). 4-[2-(2-fluorophenyl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3j):

[0074] The NMR data of compound 3j are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.65-7.60 (m, 1H), 7.52-7.50 (m,2H), 7.43-7.38 (m, 4H), 7.34 (d, J = 8.4 Hz, 2H), 7.08-7.04 (m, 1H), 6.95-6.91(m, 1H), 6.82 (td, J = 7.5, 1.2 Hz, 1H), 6.63 (td, J = 7.8, 1.2 Hz, 1H), 3.09 (dd, J = 10.8, 8.4 Hz, 1H), 2.12-2.09 (m, 1H), 1.99 (t, J = 7.8 Hz, 1H). 13 C NMR (151 MHz, CDCl3) major: δ = 163.1, 161.4, 141.0, 140.2, 133.2, 129.3, 128.7,128.4 (d, J = 8.2 Hz), 128.3 (d, J = 3.6 Hz), 127.4, 126.9, 126.6, 123.5 (d, J = 3.5 Hz), 122.9 (d, J = 16.5 Hz), 122.3 (q, J = 259.1 Hz), 114.9 (d, J = 21.4Hz), 67.8 (d,J = 1.5 Hz), 24.5 (d, J = 4.2 Hz), 15.2. 19 F NMR (565 MHz, CDCl3)major: δ = -54.51 (s, 3F), -116.27—116.30 (m, 1F), minor: -54.61 (s, 3F), -116.38—116.42 (m, 1F).GC-MS (EI, m / z, %): C 22 H 16 F4O, 372.03 (M + . 100), 287.07(39), 109.05 (43). 4-[2-(2-methoxyphenyl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3k):

[0075] The NMR data for compound 3k are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.62 (s, 1H),7.60 (s, 1H), 7.48 (d, J = 8.4 Hz, 2H), 7.44 (t, J = 7.8 Hz, 3H), 7.37-7.35 (m,3H), 7.29-7.26 (m, 3H), 7.23 (d, J = 1.8 Hz), 7.18 (dd, J = 7.8, 1.8 Hz, 2H),7.06-7.02 (m, 1H), 6.96 (t, J = 7.5 Hz, 1H), 6.91 (d, J = 8.4 Hz, 1H), 6.68 (d, J = 7.8 Hz, 1H), 6.65 (d, J = 4.2 Hz, 2H), 3.89 (s, 1H), 3.81 (s, 3H), 3.06(dd, J = 10.8, 8.4 Hz, 1H), 2.51 (t, J = 9.0 Hz, 1H), 2.06-1.99 (m, 1H), 1.94-1.89 (m, 1H). 13C NMR (151 MHz, CDCl3) mixture of diastereomers: major: δ =159.3, 158.7, 140.9, 140.6, 140.45, 140.41, 138.7, 134.1, 128.8, 128.64,128.56, 128.1, 127.9, 127.7, 127.6, 127.4, 127.3, 127.10, 127.09, 126.9,126.2, 124.0, 123.6, 122.4 (q, J = 258.8 Hz), 120.2, 119.9, 110.1, 109.8, 68.0(d, J = 2.0 Hz), 66.0 (d, J = 1.8 Hz), 55.4, 55.2, 27.1, 26.3, 15.0, 14.9. 19 FNMR (565 MHz, CDCl3) major: δ = -54.25 (s, 3F), minor: -54.39 (s, 3F).GC-MS(EI, m / z, %): C 23 H 19 F3O2, 384.05 (M + 5), 298.08 (100), 191.08 (30). 4-[2-(3-chlorophenyl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3l):

[0076] The NMR data for compound 3l are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.54 (d, J = 8.5 Hz, 2H), 7.46 (d, J = 8.0 Hz, 2H), 7.42 (t, J = 7.5 Hz, 2H), 7.34 (d, J = 7.0 Hz, 1H), 7.30 (d, J = 8.5 Hz, 2H), 7.07-7.01 (m, 2H), 6.94 (s, 1H), 6.75 (d, J =7.5 Hz, 1H), 2.94 (dd, J = 11.0, 8.0 Hz, 1H), 2.10 (dd, J = 11.0, 7.5 Hz, 1H), 1.89 (t, J = 7.8Hz, 1H). 13 C NMR (151 MHz, CDCl3) major: δ = 141.3, 140.2, 137.8, 133.9, 132.6,129.9, 129.2, 128.7, 128.3, 127.5, 127.0, 126.8, 126.7, 126.1, 122.2 (q, J = 259.2 Hz), 68.1 (d, J = (1.8 Hz), 29.9, 16.7. 19 F NMR (565 MHz, CDCl3) major: δ =-54.44 (s, 3F), minor: -54.58 (s, 3F).GC-MS (EI, m / z, %): C 22 H 16 ClF3O, 388.01 (M + . 100), 267.09 (23), 125.02 (33). 4-[2-(m-Tolyl)-1-(Trifluoromethoxy)cyclopropyl]-1,1'-Biphenyl (3m):

[0077] The NMR data for compound 3m are as follows: 1 H NMR (500 MHz, CDCl3) mixture of diastereomers: δ = 7.67 -7.64 (m,1H), 7.57-7.39 (m, 6H), 7.37-7.14 (m, 2H), 7.02 (t, J = 7.5 Hz, 1H), 6.92 (d, J = 8.0 Hz, 1H), 6.79 (s, 1H), 6.70 (d, J = 7.5 Hz, 1H), 2.98 (dd, J =11.0, 8.3Hz, 1H), 2.42 (s, 3H), 2.23 (s, 3H), 2.17 (t, J = 8.0 Hz, 1H), 2.09 (dd, J = 10.5, 7.0 Hz, 1H), 2.05 (dd, J = 10.5, 7.8 Hz, 1H); 1.90 (t, J = 7.8 Hz, 1H). 13 CNMR (151 MHz, CDCl3) mixture of diastereomers: δ = 140.9, 140.8, 140.4,140.3, 138.7, 137.8, 137.5, 135.5, 134.5, 133.3, 129.9, 129.4, 129.0, 128.8,128.7, 128.1, 127.8, 127.7, 127.5, 127.4, 127.3, 127.2, 127.1, 127.0, 126.6,126.5, 125.3, 124.9, 122.3 (q, J = 258.9 Hz), 68.2 (d, J = 1.7 Hz), 66.0, 32.6,30.2, 21.4, 21.2, 16.6, 16.4. 19 F NMR (565 MHz, CDCl3) major: δ = -54.25 (s,3F), minor: -54.44 (s, 3F).GC-MS (EI, m / z, %): C 23 H 19 F3O, 368.07 (M + 100),283.12 (47), 191.07 (39). 2-[2-([1,1'-biphenyl]-4-yl)-2-(trifluoromethoxy)cyclopropyl]naphthalene(3n):

[0078] The NMR data for compound 3n are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.72 (d, J = 7.2 Hz, 1H), 7.67 (d, J =7.8 Hz, 1H), 7.60 (d, J = 8.4 Hz, 1H), 7.49 (d, J = 8.4 Hz, 2H), 7.43-7.35(m, 9H), 7.32-7.29 (m, 1H),7.04 (dd, J = 8.4, 1.8 Hz, 1H), 3.16 (dd, J = 10.8, 8.4 Hz, 1H), 2.18 (dd, J = 10.8, 7.2 Hz, 1H), 2.04 (t, J = 7.8 Hz, 1H). 13 C NMR(151 MHz, CDCl3) major: δ = 141.0, 140.2, 133.2, 133.1, 133.0, 132.1, 129.9,128.6, 127.6, 127.5, 127.5, 127.4, 126.9, 126.8, 126.7, 126.3, 126.0, 125.5,122.3 (q, J = 259.0 Hz), 68.3 (d, J = 2.3 Hz), 30.5, 16.8. 19 F NMR (565 MHz, CDCl3) major: δ = -54.25 (s, 3F), minor: -54.46 (s, 3F). GC-MS (EI, m / z, %):C 26 H 19 F3O, 404.03 (M + 100), 319.08 (67), 165.04 (57). 2-[2-([1,1'-biphenyl]-4-yl)-2-(trifluoromethoxy)cyclopropyl]naphthalene (3o):

[0079] The NMR data for compound 3o are as follows: 1H NMR (600 MHz, CDCl3) major: δ = 8.57-8.28 (m, 1H), 8.23 ​​(s, 1H), 8.20-7.90 (m, 1H), 7.79-7.62 (m, 2H), 7.55-7.32 (m, 3H), 7.27–7.18 (m, 6H), ,6.92 (d, J = 8.4 Hz, 2H), 6.69 (d, J = 9.0 Hz, 2H), 3.63 (t, J = 9.9 Hz, 1H), 2.93-2.88 (m, 1H), 2.30 (dd, J = 9.6, 7.8 Hz, 1H). 13 C NMR (151 MHz, CDCl3)major: δ = 140.2, 139.0, 135.1, 134.1, 133.5, 131.4, 131.1, 129.1, 128.5,127.3, 127.2, 127.0, 126.7, 126.0, 125.5, 125.4, 124.7, 122.5 (q, J = (259.4Hz), 67.8, 29.5, 21.3. 19 F NMR (565 MHz, CDCl3) major: δ = -53.60 (s, 3F), minor: -54.09 (s, 3F). GC-MS (EI, m / z, %): C 30 H 21 F3O, 454.04 (M + . 100), 355.10(73), 215.03 (15). (2-[1,1'-biphenyl]-4-yl-2-trifluoromethoxycyclopropyl)thiophene (3p):

[0080] The NMR data for compound 3p are as follows: 1 H NMR (500 MHz, CDCl3) major: δ = 7.57 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 8.0 Hz, 2H), 7.44-7.40 (m, 4H), 7.34 (t, J =7.3 Hz, 1H), 6.99 (d, J = 5.0Hz, 1H), 6.75 (t, J = 4.0 Hz, 1H), 6.56 (d, J = 3.0 Hz, 1H), 3.09 (dd, J = 10.5, 8.0 Hz, 1H), 2.19 (dd, J = 10.8, 7.3 Hz, 1H), 1.90 (t, J = 7.5 Hz, 1H). 13 C NMR(151 MHz, CDCl3) major: δ = 141.2, 140.2, 139.5, 132.9, 129.7, 128.7, 127.5,127.0, 126.7, 126.5, 125.4, 124.2, 122.2 (q, J = 259.2 Hz), 68.1 (d, J = 2.3Hz), 25.6, 18.6. 19 F NMR (565 MHz, CDCl3) major: δ = -54.49 (s, 3F), minor: -54.55 (s, 3F).GC-MS (EI, m / z, %): C 20 H 15 F3OS, 360.00 (M + . 87), 275.05 (100), 191.09 (57). (2-Methyl-2-phenyl-1-trifluoromethoxycyclopropyl)-1,1'-biphenyl(3q):

[0081] The NMR data for compound 3q are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.52-7.50 (m, 2H), 7.41-7.37 (m,4H), 7.33-7.31 (m, 1H), 7.18 (dt, J = 8.4, 2.4 Hz, 2H), 7.12-7.09 (m, 2H), 7.07-7.02 (m, 3H), 2.20 (d, J = 7.8 Hz, 1H), 1.79 (dd, J =7.8, 1.2 Hz, 1H),1.76 (s, 3H); mixture of diastereomers: 7.70-7.61 (m, 1H), 7.52- 7.37 (m,6H), 7.33-7.31 (m, 1H), 7.19-7.02 (m, 6H), 2.20 (d, J = 7.8 Hz, 1H), 2.11 (dd, J = 7.2, 1.8 Hz, 1H), 1.79 (dd, J = 7.8, 1.2 Hz, 1H), 1.71 (d, J = 7.2 Hz, 1H), 1.76 (s, 3H), 1.11 (s, 3H). 13 C NMR (151 MHz, CDCl3) mixture of diastereomers:δ = 141.2, 140.8, 140.7, 140.4, 140.3, 139.8, 135.9, 135.3, 130.3, 129.2,129.0, 128.84, 128.81, 128.6, 128.5, 128.3, 128.0, 127.7, 127.5, 127.4,127.2, 127.1, 126.9, 126.7, 126.33, 126.26, 122.6 (q, J = 258.4 Hz), 122.3 (q, J = 258.7 Hz), 70.0 (d, J = 1.8 Hz), 68.9 (d, J = 1.8 Hz), 34.3, 32.0, 24.4,23.0, 21.2, 20.7. 19 F NMR (565 MHz, CDCl3) major: δ =-54.10 (s, 3F), minor: -54.36 (s, 3F). GC-MS (EI, m / z, %): C 23 H 19 F3O, 368.07 (M + . 100), 275.01 (47), 129.08 (35). 4-[2-Methyl-2-(p-Tolyl)-1-(Trifluoromethoxy)cyclopropyl]-1,1'-Biphenyl (3r):

[0082] The NMR data for compound 3r are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.47 (d, J = 8.4 Hz, 2H), 7.36-7.33(m, 4H), 7.28-7.25 (m, 1H), 7.15-7.13 (m, 2H), 6.90 (d, J = 7.8 Hz, 2H), 6.86 (d, J = 7.8 Hz, 2H), 2.14 (s, 3H), 2.11 (dd, J = 6.0, 1.2 Hz, 1H), 1.71 (dt, J = 6.0, 1.2 Hz, 1H), 1.69 (s, 3H), minor: 7.64-7.62 (m, 4H), 7.56 (dd, J = 7.8, 1.5 Hz, 2H), 7.43 (t, J = 7.8 Hz, 3H), 7.30 (d, J = 6.6 Hz, 2H), 7.18 (d, J = 7.8 Hz, 2H), 2.35 (s, 3H), 2.04 (d, J = 7.2 Hz, 1H), 1.63 (dd, J = 7.8, 1.2 Hz, 1H), 1.05 (s, 3H). 13 C NMR (151 MHz, CDCl3) major: δ = 140.4, 139.7, 137.7,136.0, 135.8, 128.72, 128.65, 128.5, 127.4, 127.2, 126.8, 126.3, 122.6 (q, J = 258.5 Hz), 70.1 (d, J = 1.5 Hz), 34.0, 23.1, 21.3, 20.9; minor: 141.1, 140.5,137.8, 136.2, 135.4, 129.2, 129.1, 129.0, 128.8, 128.0, 127.5, 127.1, 127.09,69.0 (d, J= 1.7 Hz), 31.7, 24.5, 21.1, 20.7. 19 F NMR (565 MHz, CDCl3) major: δ= -54.03 (s, 3F), minor: -54.25 (s, 3F).GC-MS (EI, m / z, %): C 24 H 21 F3O, 382.05 (M) + 100), 275.00 (70), 143.09 (40). 4-[1-Phenylacetyl-2-(trifluoromethoxy)-[1,1'-bicyclopropane]-2-yl]-1,1'-biphenyl(3s):

[0083] The NMR data for compound 3s are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.68-7.64 (m,3H), 7.51 (d, J = 7.8 Hz, 2H), 7.47 (t, J = 7.2 Hz, 2H), 7.40-7.36 (m, 8H), 7.32-7.28 (m, 2H), 7.14 (d, J = 7.8 Hz, 2H), 7.07-7.00 (m, 6H), 6.96 (d, J = 7.2 Hz, 2H), 2.01 (d, J = 7.2 Hz, 1H), 1.90 (d, J = 7.2 Hz, 1H), 1.78 (d, J = 7.8 Hz, 1H), 1.68 (d, J = 7.2 Hz, 1H), 1.53-1.48 (m, 1H), 0.72-0.69 (m, 1H), 0.68-0.63 (m, 1H), 0.55-0.50 (m, 1H), 0.34-0.30 (m, 1H), 0.28-0.23 (m, 1H),0.21-0.15 (m, 1H), 0.11-0.03 (m, 2H), -0.13--0.18 (m, 1H). 13C NMR (151 MHz, CDCl3) mixture of diastereomers: δ = 141.0, 140.5, 140.4, 139.7, 139.1,138.9, 136.3, 135.5, 130.0, 129.9, 129.6, 128.8, 128.7, 128.0, 127.7, 127.5,127.3, 127.1, 126.94, 126.89, 126.82, 126.76, 126.4, 126.3, 122.7 (q, J = 258.7 Hz), 70.0 (d, J = 1.7 Hz), 68.7 (d, J = 1.4 Hz), 40.2, 37.4, 18.7, 18.5,16.5, 15.4, 4.75, 4.65, 3.3, 3.2. 19 F NMR (565 MHz, CDCl3) major: δ = -54.03(s, 3F), minor: -54.26 (s, 3F).GC-MS (EI, m / z, %): C 25 H 21 F3O, 394.11 (M + 7),365.07 (100), 251.01 (35). 4-[2,2-diphenyl-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3t):

[0084] The NMR data for compound 3t are as follows: 1 H NMR (500 MHz, CDCl3) δ = 7.58-7.57 (m, 4H), 7.47 (d, J = 8.0 Hz, 2H), 7.43 (t, J = 7.5 Hz, 2H), 7.36 (t, J = 7.5 Hz, 3H), 7.31 (d, J = 8.5 Hz, 2H), 7.25 (t, J = 7.3 Hz, 1H), 7.13 (d, J = 7.5 Hz, 2H), 7.03 (t, J = 7.3 Hz, 2H), 6.98 (t,J = 7.5 Hz, 1H), 2.54 (d, J = 7.5 Hz, 1H), 2.49 (d, J = 7.5 Hz, 1H). 13 C NMR (151 MHz, CDCl3) δ = 140.5, 140.3, 140.2, 140.0, 135.5, 129.6,129.5, 128.7, 128.3, 128.0, 127.4, 127.3, 126.9, 126.8, 126.5, 126.4, 122.2(q, J = 259.1 Hz), 69.2 (d, J = 2.3 Hz), 43.6, 21.8. 19 F NMR (565 MHz, CDCl3) δ =-54.03 (s, 3F).GC-MS (EI, m / z, %): C 28 H 21 F3O, 430.07 (M + 100), 345.09 (80), 191.07 (33). 4-[(2R,3S)-2-methyl-3-phenyl-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3u):

[0085] The NMR data for compound 3u are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.65-7.52 (m,5H), 7.46-7.22 (m, 7H), 7.13-6.85 (m, 2H), 2.58 (d, J = 7.8 Hz, 1H), 2.38 (d, J = 7.8 Hz, 1H), 2.20 (p, J = 6.6 Hz, 1H), 1.99 (p, J = 6.6 Hz, 1H), 1.55 (d, J = 6.0 Hz, 3H), 1.10 (d, J = 6.0 Hz, 3H). 13C NMR (151 MHz, CDCl3) mixture of diastereomers: δ = 141.7, 141.1, 140.4, 140.3, 136.4, 135.7, 134.0, 133.6,131.0, 130.8, 128.8, 128.7, 128.3, 128.2, 128.0, 127.9, 127.6, 127.5, 127.2,127.0, 126.62, 126.60, 126.3, 122.0 (q, J = 258.7 Hz), 71.9, 71.6, 36.5, 35.4,24.2, 24.1, 15.2, 12.9. 19 F NMR (565 MHz, CDCl3) minor: δ = -53.51 (s, 3F), major: -53.53 (s, 3F). GC-MS (EI, m / z, %): C 23 H 19 F3O, 368.08 (M + . 100), 275.01(27), 129.09 (23). 4-[(2S,3S)-2-methyl-3-phenyl-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3v):

[0086] The NMR data for compound 3v are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.61-7.60 (m, 2H), 7.54 (dt, J = 8.4, 1.8 Hz, 2H), 7.46-7.43 (m, 2H), 7.38-7.36 (m, 3H), 7.22-7.19 (m, 3H), 6.99-6.97 (m, 2H), 3.01 (d, J = 11.4 Hz, 1H), 2.29-2.24 (m, 1H), 1.25 (d, J = 6.6 Hz, 3H). 13C NMR (151 MHz, CDCl3) major: δ = 141.3, 140.3, 135.3, 132.0,131.1, 129.8, 128.8, 128.0, 127.6, 127.1, 126.8, 126.3, 122.4 (q, J = 258.5Hz), 70.1 (d, J = 1.5 Hz), 33.0, 25.1, 10.5. 19 F NMR (565 MHz, CDCl3) minor: δ =-53.00 (s, 3F); major: -53.64 (s, 3F).GC-MS (EI, m / z, %): C 23 H 19 F3O, 368.08 (M + . 100), 275.01 (27), 129.09 (23). 4-[(2S)-2-((E)-styryl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3w):

[0087] The NMR data for compound 3w are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.63-7.59 (m,4H), 7.55 (dd, J = 6.6, 2.4 Hz, 2H), 7.46 (t, J = 7.8 Hz, 2H), 7.42-7.33 (m,1H), 7.25-7.21 (m, 2H), 7.17-7.10 (m, 3H), 6.63 (d, J = 15.6 Hz, 1H), 6.58 (d, J = 15.6 Hz, 1H), 6.13 (dd, J = 16.2, 9.0 Hz, 1H), 5.31 (dd, J = 16.2, 9.6 Hz, 1H), 2.54 (dd, J = 17.4, 9.6 Hz, 1H), 2.04 (dd, J = 16.5, 9.3 Hz, 1H), 1.99 (dd, J =10.5, 6.9 Hz, 1H), 1.93 (dd, J = 10.2, 7.2 Hz, 1H), 1.80 (t, J = 7.2Hz, 1H), 1.54 (t, J = 7.2 Hz, 1H). 13 C NMR (151 MHz, CDCl3) mixture of diastereomers: δ = 141.6, 141.2, 140.3, 140.2, 137.2, 136.3, 135.9, 132.8,129.2, 128.9, 128.84, 128.81, 128.75, 128.6, 127.8, 127.6, 127.5, 127.4,127.1, 127.06, 126.7, 126.2, 125.9, 122.1 (q, J = 259.9 Hz), 68.3 (d, J = 2.0Hz), 65.9 (d, J = 2.0 Hz), 29.8, 27.4, 19.0, 18.9. 19 F NMR (565 MHz, CDCl3)major: δ = -54.36 (s, 3F); minor: -54.25 (s, 3F).GC-MS (EI, m / z, %): C 24 H 19 F3O, 380.07 (M + . 100), 295.12 (70), 91.07 (55). 5-[2-(4-methoxystyryl)-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3x):

[0088] The NMR data for compound 3x are as follows: 1 H NMR (500 MHz, CDCl3) mixture of diastereomers: δ = 7.64-7.61 (m,4H), 7.56-7.38 (m, 5H), 7.35 (d, J = 9.0 Hz, 2H), 7.10 (d, J = 8.5 Hz, 2H), 6.89 (d, J =8.5 Hz, 2H), 6.77 (d, J = 9.0 Hz, 2H), 6.58 (d, J = 16.0 Hz, 1H),6.52 (d, J = 16.0 Hz, 1H), 5.99 (dd, J = 16.0, 9.0 Hz, 1H), 5.18 (dd, J = 15.8,9.0 Hz, 1H), 3.83 (s, 3H), 3.76 (s, 3H), 2.52 (q, J = 9.0 Hz, 1H), 2.01 (q, J = 9.0 Hz, 1H), 1.97 (dd, J = 10.5, 7.0 Hz, 1H), 1.92 (dd, J = 10.0, 7.0 Hz, 1H),1.78 (t, J = 7.0 Hz, 1H), 1.52 (t, J = 7.0 Hz, 1H). 13 C NMR (151 MHz, CDCl3)mixture of diastereomers: δ = 159.0, 158.9, 141.4, 140.8, 140.4, 140.3,138.2, 134.2, 131.4, 131.0, 130.1, 129.9, 129.8, 128.80, 128.78, 127.54,127.47, 127.22, 127.16, 127.11, 127.08, 127.04, 127.03, 126.5, 124.8, 123.5,122.2 (q, J = 259.1 Hz), 114.0, 113.9, 67.8 (d, J = 2.3 Hz), 66.7 (d, J = 1.8Hz), 55.3, 55.2, 31.3, 28.5, 19.0, 18.3. 19 F NMR (565 MHz, CDCl3) major: δ = -54.31 (s, 3F), minor: -54.19 (s, 3F).GC-MS (EI, m / z, %): C 25 H 21 F3O2, 410.11 (M +3), 324.06 (100), 265.09 (7). (2-[1,1'-biphenyl]-4-yl-2-trifluoromethoxycyclopropyl)(phenyl)thion (3y):

[0089] The NMR data for compound 3y are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: major: δ = 7.60-7.52(m, 4H), 7.44-7.13 (m, 10H), 3.12 (dd, J = 10.2, 6.6 Hz, 1H), 2.50 (dd, J = 9.6, 6.6 Hz, 1H), 2.21-2.18 (m, 1H), 2.13 (dd, J = 9.6, 7.8 Hz, 1H), 1.84 (t, J = 7.5 Hz, 1H), 1.69 (t, J = 7.2 Hz, 1H). 13 C NMR (151 MHz, CDCl3) mixture of diastereomers: δ = 141.7, 141.3, 140.4, 140.3, 137.2, 136.3, 136.0, 132.9,129.3, 129.0, 128.89, 128.86, 128.8, 128.6, 127.9, 127.7, 127.6, 127.5,127.15, 127.10, 126.8, 126.3, 126.0, 122.5 (q, J = 259.3 Hz), 122.1 (q, J = 259.6 Hz), 68.4 (d, J = 2.0 Hz), 66.0 (d, J = 2.1 Hz), 29.8, 27.5, 19.1,19.0. 19 F NMR (565 MHz, CDCl3) major: δ = -54.42 (s, 3F), minor: -54.44 (s, 3F). GC-MS (EI, m / z, %): C 22 H 17F3OS, 386.02 (M + 5), 277.02 (93), 199.09 (100). 4-[2-Butoxy-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3z):

[0090] The NMR data for compound 3z are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: 7.63-7.59 (m, 4H),7.53-7.35 (m, 3H), 7.46 (t, J = 7.8 Hz, 2H), 3.79 (dd, J = 8.4, 5.4 Hz, 1H), 3.74 (dt, J = 9.0, 6.6 Hz, 1H), 3.66 (dt, J = 9.0, 6.6 Hz, 1H), 3.42 (dt, J = 9.0, 6.6 Hz, 1H), 3.24-3.19 (m, 1H), 1.86-1.62 (m, 2H) 1.48-1.42 (m, 2H), 1.34-1.30 (m, 2H), 1.17-1.04 (m, 2H), 0.91-0.83 (m, 2H), 0.97 (t, J = 7.2 Hz, 3H), 0.73 (t, J = 7.5 Hz, 3H). 13 C NMR (151 MHz, CDCl3) mixture of diastereomers: major: δ = 140.8, 140.59, 140.58, 140.4, 137.5, 133.7, 128.81,128.77, 127.5, 127.45, 127.37, 127.3, 127.0, 126.7, 126.3, 122.3 (q, J = 259.3Hz), 71.7, 70.5, 66.0 (d, J = 2.0 Hz), 64.1 (d, J= 1.8 Hz), 61.9, 61.8, 31.7,31.3, 19.2, 19.0, 18.6, 18.0, 13.8, 13.6. 19 F NMR (565 MHz, CDCl3) major: δ = -54.32 (s, 3F), minor: -54.53 (s, 3F). GC-MS (EI, m / z, %): C 20 H 21 F3O2, 350.07 (M + 27), 265.04 (60), 179.07 (100). 9-[2-([1,1'-biphenyl]-4-yl)-2-(trifluoromethoxy)cyclopropyl]-9H-carbazole (3aa):

[0091] The NMR data for compound 3aa are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.91 (d, J = 7.8 Hz, 2H), 7.41 (br, 2H), 7.33-7.27 (m, 6H), 7.25-7.22 (m, 1H), 7.16-7.12 (m, 4H), 7.04 (d, J = 8.4 Hz, 2H), 4.12 (dd, J = 9.6, 6.6 Hz, 1H), 2.73 (t, J = 9.0 Hz, 1H), 2.65 (dd, J = 8.4, 6.6 Hz, 1H). 13 C NMR (151 MHz, CDCl3) δ 140.7, 140.1, 140.0, 132.8, 128.6,127.2, 126.8, 126.2, 125.6, 125.0, 123.3 (d, J = 1.7 Hz), 122.3 (q, J = 259.9Hz), 120.1, 119.8, 109.9, 66.0 (d, J = 2.0 Hz), 39.4, 19.2. 19 F NMR (565 MHz, CDCl3) δ -54.04 (s, 3F).GC-MS (EI, m / z,%): C 28 H 20 F3ON, 443.06 (M + . 100), 277.04(50), 191.10 (71). 4-[2-hexyl-1-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3ab):

[0092] The NMR data for compound 3ab are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.61-7.55 (m,4H), 7.48-7.41 (m, 3H), 7.38-7.32 (m, 2H), 1.62-1.08 (m, 10H), 0.90 (t, J = 7.2 Hz, 3H), 0.83 (t, J = 7.2 Hz, 3H). 13 C NMR (151 MHz, CDCl3) mixture of diastereomers: δ = 141.1, 140.6, 140.52, 140.46, 139.6, 134.8, 129.3, 128.8,127.5, 127.4, 127.14, 127.10, 127.08, 126.9, 126.4, 122.7 (q, J = 257.9 Hz), 122.4 (q, J = 258.4 Hz), 67.4 (d, J = 2.1 Hz), 66.1 (d, J = 2.1 Hz), 31.8, 31.7,29.7, 29.4, 29.1, 29.0, 28.9, 28.6, 28.2, 28.0, 25.2, 22.7, 22.5, 17.6, 15.9,14.1, 14.0. 19 F NMR (565 MHz, CDCl3) major: δ = -54.14 (s, 3F), minor: -54.24(s, 3F). GC-MS (EI, m / z, %): C 22 H 25 F3O, 362.12 (M +. 60), 263.99 (100), 191.09 (33). tert-butyl 1-([1,1'-biphenyl]-4-yl)-1-(trifluoromethoxy)-5-azaspiro[2,3]hexane-5-carboxylic acid ester (3ac):

[0093] The NMR data for compound 3ac are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.61 (d, J = 8.4 Hz, 2H), 7.58 (d, J = 7.8Hz, 2H), 7.44 (t, J = 7.8 Hz, 2H), 7.37-7.34 (m, 3H), 4.31 (d, J = 9.0 Hz, 1H), 4.07 (d, J = 9.0 Hz, 1H), 3.71 (d, J = 8.4 Hz, 1H), 3.55 (d, J = 8.4 Hz, 1H), 1.73 (s, 2H), 1.44 (s, 9H). 13 C NMR (151 MHz, CDCl3) δ = 156.0, 141.3, 140.2,133.8, 128.8, 127.6, 127.4, 127.2, 127.1, 122.4 (q, J = 259.4 Hz), 79.8, 65.0 (d, J = 1.8 Hz), 53.2 (br), 28.4, 26.5, 19.0. 19 F NMR (565 MHz, CDCl3) major: δ= -54.92 (s, 3F).GC-MS (EI, m / z, %): C 23 H 24 F3NO3, 419.14 (M + 5), 290.05 (80), 57.07 (100). (8S,9S,10R,13R,14S,17R)-3-[(4-{2-([1,1'-biphenyl]-4-yl)-2-(trifluoromethoxy)cyclopropyl}benzyl)oxy]-10,13-dimethyl-17-[(R)-6-methylheptane-2-yl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecano-1H-cyclopenta[a]phenanthrene(3ad):

[0094] The NMR data for compound 3ad are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.66 – 7.61 (m,1H), 7.53 (d, J = 7.8 Hz, 2H), 7.49 – 7.45 (m, 4H), 7.44 – 7.39 (m, 4H), 7.37 – 7.32 (m, 4H), 7.31 – 7.27 (m, 2H), 5.37 (d, J = 3.6 Hz, 1H), 5.30 (d, J = 3.0Hz, 1H), 4.59 (s, 2H), 4.43 (s, 2H), 3.34 – 2.29 (m, 1H), 3.22 – 3.16 (m,1H), 2.96 (t, J = 9.6 Hz, 1H), 2.47 – 2.44 (m, 1H), 2.39 (t, J = 9.0 Hz, 1H),2.36 – 2.29 (m, 2H), 2.22 (t, J = 12.0 Hz, 1H), 2.13 (t, J = 7.8 Hz, 1H), 2.09– 1.79 and 1.60 – 1.23 and 1.19 – 0.87 (m, 40H), 0.69 and 0.68 (s, 3H). 13 C NMR(151 MHz, CDCl3) mixture of diastereomers: δ = 141.03, 141.02, 141.01,140.95, 140.87, 140.5, 140.3, 138.7, 137.8, 137.4 (d, J= 2.0 Hz), 134.7,133.8, 133.2 (d, J = 1.5 Hz), 130.0, 129.97, 128.9, 128.7, 128.5, 128.10,128.07, 127.55, 127.54, 127.47, 127.33, 127.28, 127.1, 127.0, 126.7, 126.5,122.3 (q, J = 259.1 Hz), 121.64, 121.58, 78.8, 78.75, 78.7, 69.7 (d, J = 3.9Hz), 68.3 (t, J = 1.5 Hz), 66.0 (d, J = 2.1 Hz), 56.8, 56.79, 56.2, 50.23,50.19, 42.37, 42.35, 39.83, 39.81, 39.6, 39.22, 39.19, 39.16, 37.3, 37.2,36.95, 36.89, 36.2, 35.8, 32.5, 32.2, 32.0, 31.98, 31.96, 31.94, 31.90,30.13, 30.11, 29.42, 29.38, 28.51, 28.48, 28.3, 28.1, 27.3, 26.4, 24.3, 23.9, 23.5, 22.9, 22.8, 22.6, 21.1, 21.08, 19.45, 19.38, 18.8, 16.8, 16.5, 14.2, 11.91, 11.90. 19 F NMR (565 MHz, CDCl3) major (2 diastereomers): δ = -54.296 (s,3F), -54.301 (s, 3F), minor: -54.48 (s, 3F).HRMS (ESI) m / z: calc'd forC 50 H 64 F3O2[M+H] + 753.4853, found 753.4849. Isopropyl 2-[4-(2-([1,1'-biphenyl]-4-yl)-1-(4-chlorophenyl)-2-(trifluoromethoxy)cyclopropyl)phenoxy]-2-methylpropionate (3ae):

[0095] The NMR data for compound 3ae are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.55 (d, J = 7.8Hz, 2H), 7.52 (d, J = 7.8 Hz, 2H), 7.46 – 7.39 (m, 6H), 7.34 – 7.29 (m, 3H), 7.26 – 7.23 (m, 2H), 7.34 – 7.29 (m, 3H), 6.98 (s, 2H), 6.91 (d, J = 8.4 Hz, 2H), 6.80 (d, J = 8.4 Hz, 2H), 6.49 (d, J = 8.4 Hz, 2H), 5.09 – 5.03 (m, 1H), 4.94 – 4.87 (m, 1H), 2.46 (d, J = 7.2 Hz, 1H), 2.42 (d, J = 7.8 Hz, 1H), 2.40 (d, J = 7.2 Hz, 1H), 2.36 (d, J = 7.2 Hz, 1H), 1.59 (s, 6H), 1.42 (s, 6H), 1.15(dd, J = 6.0, 1.8 Hz, 6H), 1.02 (d, J = 6.0 Hz, 3H), 0.99 (d, J = 6.0 Hz, 3H). 13 CNMR (151 MHz, CDCl3) mixture of diastereomers: δ = 173.7, 173.6, 154.7,154.1, 140.5, 140.4, 140.18, 140.16, 139.2, 138.9, 135.20, 135.15, 133.2,132.9, 132.6, 132.3, 132.0, 131.2, 131.0, 130.7, 130.3, 130.1, 128.8, 128.7,128.6, 128.2, 127.5, 127.45, 127.4, 127.0, 126.9, 126.7, 126.5, 122.14 (q,J = 259.1 Hz), 122.12 (q, J = 259.1 Hz), 118.4, 118.3, 117.2, 79.1, 79.0, 69.2 (d, J = 1.8 Hz), 69.1 (d, J = 1.8 Hz), 69.0, 68.9, 42.24, 42.18, 29.75, 29.71,25.52, 25.46, 25.3, 25.0, 21.9, 21.45, 21.41, 21.38. 19 F NMR (565 MHz, CDCl3)major: δ = -54.16 (s, 3F), minor: -54.25 (s, 3F).HRMS (ESI) m / z: calc'd forC 35 H 33 ClF3O4[M+H] + 609.2014, found 609.2019. (8R,9S,13S,14S)-3-[2-([1,1'-biphenyl]-4-yl)-2-(trifluoromethoxy)cyclopropyl]-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthrene-17-one (3af):

[0096] The NMR data for compound 3af are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.61 (t, J = 7.8Hz, 2H), 7.55 (d, J = 7.8 Hz, 2H), 7.49 – 7.44 (m, 4H), 7.55 (t, J = 7.8 Hz, 2H), 7.37 (t, J = 7.8 Hz, 2H), 7.34 – 7.30 (m, 3H), 7.29 (d, J = 8.4 Hz, 1H), 7.01 (dd, J = 16.2, 7.8 Hz, 1H), 6.70 (d, J = 1.8 Hz, 1H), 6.68 (d, J =1.8 Hz,1H), 6.59 (d, J = 2.4 Hz, 1H), 6.56 (dd, J = 7.8, 2.4 Hz, 1H), 2.96 – 2.94 (m,1H), 2.91 – 2.88 (m, 1H), 2.79 – 2.64 (m, 4H), 2.54 – 2.44 (m, 2H), 2.36 –2.26 (m, 2H), 2.20 – 1.97 (m, 8H), 1.95 – 1.86 (m, 4H), 1.81 (td, J = 7.8, 1.8Hz, 1H), 1.66 – 1.24 (m, 14H), 0.93 and 0.87 (s, 3H). 13 C NMR (151 MHz, CDCl3)mixture of diastereomers: δ = 220.8, 140.91, 140.88, 140.4, 137.94, 137.92,136.0, 133.4, 133.3, 133.1, 133.0, 130.2, 130.0, 129.1, 128.8, 128.77, 128.6,127.5, 127.3, 127.1, 127.0, 126.6, 126.4, 125.7, 125.0, 124.98, 124.93,124.90, 122.3 (d, J = 259.3 Hz), 68.2 (d, J = 1.8 Hz), 50.5, 48.0, 44.15,44.14, 38.0, 35.8, 31.5, 29.89, 29.83, 29.2, 26.43, 26.41, 25.6, 25.5, 21.6,17.0, 13.9. 19 F NMR (565 MHz, CDCl3) major (2 diastereomers): δ = -54.28 (s,3F), -54.29 (s, 3F), minor (2 diastereomers): -54.41 (s, 3F), -54.43 (s, 3F).HRMS (ESI) m / z: calc’d for C 34 H 33 F3O2K [M+K] +569.2064, found 569.2071. 1-[3-(2-([1,1'-biphenyl]-4-yl)-1-(4-tert-butylphenyl)-2-(trifluoromethoxy)cyclopropyl)propyl]-4-(diphenylmethoxy)piperidine (3ag):

[0097] The NMR data for compound 3ag are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.45 (d, J = 7.8 Hz, 2H), 7.37 (t, J = 7.8 Hz, 2H), 7.33 – 7.26 (m, 11H), 7.24 (d, J = 8.4 Hz, 2H), 7.07 (d, J = 8.4Hz, 2H), 7.03 (d, J = 8.4 Hz, 2H), 6.85 (d, J = 7.8 Hz, 2H), 5.5 (s, 1H), 3.4(s, 1H), 2.7 (s, 2H), 2.29 – 2.25 (m, 2H), 2.07 – 2.01 (m, 4H), 1.88 – 1.83(m, 2H), 1.74 – 1.67 (m, 2H), 1.53 – 1.48 (m, 2H), 1.26 (t, J = 7.2 Hz, 2H), 1.16 (s, 9H). 13 C NMR (151 MHz, CDCl3) major: δ = 149.2, 142.9, 140.6, 139.7,136.3, 135.5, 129.4, 128.7, 128.3, 127.3, 127.1, 126.9, 126.2, 124.6, 122.6(d, J = 258.5 Hz), 80.0, 70.3, 58.4, 51.0, 38.7, 34.3, 33.6, 31.4, 31.3, 24.8,20.9. 19F NMR (565 MHz, CDCl3) major: δ = -53.95 (s, 3F), minor: -54.13 (s, 3F). HRMS (ESI) m / z: calc'd for C 47 H 51 F3NO2[M+H] + 718.3866, found 718.3859. Ethyl 2-[3-(2-([1,1'-biphenyl]-4-yl)-2-(trifluoromethoxy)cyclopropyl)-4-isobutoxyphenyl]-4-methylthiazol-5-carboxylic acid ester (3ah):

[0098] The NMR data for compound 3ah are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.66 (dd, J = 8.4, 2.4 Hz, 1H), 7.46(d, J = 7.8 Hz, 2H), 7.37 – 7.25 (m, 7H), 7.20 (s, 1H), 6.73 (d, J = 8.4 Hz, 1H), 4.31 (q, J = 7.2 Hz, 2H), 3.80 (d, J = 6.6 Hz, 1H), 3.1 (d, J = 9.6 Hz,1H), 2.7 (s, 3H), 2.29 – 2.21 (m, 1H), 2.11 – 2.05 (m, 1H), 1.35 (t, J = 7.2Hz, 3H), 1.16 (d, J = 6.6 Hz, 6H). 13 C NMR (151 MHz, CDCl3) major: δ = 169.9,162.4, 160.9, 160.7, 140.7, 140.4, 133.7, 128.7, 128.6, 127.3, 127.0, 126.99,126.90, 126.5, 126.4, 125.0, 124.8, 122.4 (q, J = 258.8 Hz), 110.7, 74.6, 67.9(d, J= 1.8 Hz), 61.1, 28.5, 26.3, 19.4, 17.5, 15.1, 14.4. 19 F NMR (565 MHz, CDCl3) major: δ = -54.35 (s, 3F), minor: -54.37 (s, 3F).HRMS (ESI) m / z: calc'd for C 33 H 33 F3NO4S [M+H] + 569.2077, found 569.2082. 4-[2-(4-chlorophenyl)-2-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3ai):

[0099] The NMR data for compound 3ai are as follows: 1 H NMR (500 MHz, CDCl3) mixture of diastereomers: δ = 7.63-7.30 (m,9H), 7.22-6.92 (m, 4H), 2.99 (dd, J = 10.5, 8.3 Hz, 1H), 2.37 (dd, J = 10.0, 9.0 Hz, 1H), 2.14 (t, J = 7.8 Hz, 1H), 2.09 (dd, J = 10.5, 7.5 Hz, 1H), 2.01(dd, J = 10.5, 7.8 Hz, 1H), 1.86 (t, J = 7.8 Hz, 1H). 13 C NMR (151 MHz, CDCl3)mixture of diastereomers: δ = 140.7, 140.4, 139.9, 139.4, 134.5, 134.3,134.0, 133.4, 133.0, 128.85, 128.79, 128.76, 128.71, 128.42, 128.35, 127.7,127.3, 127.0, 126.97, 126.8, 126.7, 122.2 (q, J = 258.6 Hz), 67.7 (d, J = 2.4Hz), 65.6 (d,J = 2.3 Hz), 32.2, 29.9, 16.7, 16.6. 19 F NMR (565 MHz, CDCl3)major: δ = -54.52 (s), minor: -54.66 (s).GC-MS (EI, m / z, %): C 22 H 16 ClF3O, 388.00 (M) + 100), 303.02 (82), 125.04 (43). 4-[2-(4-bromophenyl)-2-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3aj):

[0100] The NMR data for compound 3aj are as follows: 1 H NMR (600 MHz, CDCl3) mixture of diastereomers: δ = 7.63-7.44 (m,3H), 7.41-7.30 (m, 6H), 7.14 (d, J = 8.4 Hz, 2H), 6.93 (d, J = 8.4 Hz, 2H), 2.99 (dd, J = 10.8, 8.4 Hz, 1H), 2.36 (dd, J = 10.2, 8.4 Hz, 1H), 2.14 (t, J = 7.8 Hz, 1H), 2.08 (dd, J = 10.8, 7.8 Hz, 1H), 2.01 (dd, J = 10.2, 7.8 Hz, 1H), 1.85 (t, J = 7.8 Hz, 1H). 13C NMR (151 MHz, CDCl3) mixture of diastereomers: δ =140.7, 140.3, 139.9, 139.4, 138.6, 134.2, 133.35, 133.28, 131.8, 131.74,131.6,131.5, 131.4, 131.2, 128.8, 128.75, 128.70, 128.4, 128.1, 127.8, 127.3,127.0, 126.96, 126.8, 126.7, 126.66, 122.7, 122.2 (q, J = 259.3 Hz), 122.0, 67.7 (d, J = 1.8 Hz), 65.6 (q, J = 2.1 Hz), 32.3, 29.9, 16.6, 16.5. 19 F NMR (565MHz, CDCl3) major: δ = -54.46 (s), minor: -54.61 (s).GC-MS (EI, m / z, %):C 22 H 16 BrF3O, 431.90 (M + . 87), 268.08 (100), 199.02 (25). 4-[2-(4-tert-butylphenyl)-2-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3ak):

[0101] The NMR data for compound 3ak are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.49-7.47 (m, 2H), 7.38 (t, J = 7.8Hz, 2H), 7.32 (d, J = 8.4 Hz, 2H), 7.29 (m, 1H), 7.19 (d, J = 10.2 Hz, 2H), 6.90 (d, J = 8.4 Hz, 2H), 2.94 (dd, J = 10.8, 6.0 Hz, 1H), 2.05 (dd, J = 10.8, 7.2 Hz, 1H), 1.81 (t,J = 7.5 Hz, 1H), 1.23 (s, 9H), minor: 7.62-7.57 (m, 4H), 7.45-7.34 (m, 5H), 7.21-7.16 (m, 4H), 2.38 (dd, J = 10.2, 7.8 Hz, 1H), 2.10(t, J = 7.8 Hz, 1H), 2.0 (dd, J = 9.9, 7.5 Hz, 1H), 1.34 (s, 9H). 13 C NMR (151MHz, CDCl3) mixture of diastereomers: δ = 151.5, 151.1, 140.9, 140.7, 139.7,139.1, 136.5, 135.2, 134.1, 130.9, 129.7, 129.5, 128.9, 128.79, 128.75,128.4, 127.24, 127.19, 127.1, 127.0, 126.9, 126.5, 126.0, 125.5, 125.0, 122.3(q, J = 258.7 Hz), 68.5 (d, J = 1.7 Hz), 66.3 (d, J = 1.7 Hz), 34.65, 34.58,32.1, 31.4, 31.2, 29.8, 17.2, 16.7. 19 F NMR (565 MHz, CDCl3) major: δ = -54.19(s, 3F), -54.36 (s, 3F).GC-MS (EI, m / z, %): C 26 H 25 F3O, 410.08 (M + 3), 353.00(100), 199.01 (26). 4-[2-(3-methoxyphenyl)-2-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3al):

[0102] The NMR data for compound 3al are as follows: 1H NMR (500 MHz, CDCl3) mixture of diastereomers: δ = 7.67-7.04 (m,9H), 7.06-6.76 (m, 4H), 3.87 (s, 3H), 3.68 (s, 3H), 3.01 (dd, J = 10.5, 8.0Hz, 1H), 2.11 (t, J = 9.0 Hz, 1H), 2.18-1.90 (m, 2H). 13 C NMR (151 MHz, CDCl3)mixture of diastereomers: δ = 159.7, 159.1, 141.1, 140.7, 140.5, 139.8,139.1, 135.6, 134.8, 133.7, 129.7, 129.1, 128.8, 128.73, 128.68, 128.4,127.2, 127.15, 127.0, 126.9, 126.8, 126.6, 122.2 (q, J = 259.1 Hz), 121.9,118.1, 115.1, 114.1, 113.2, 112.0, 68.3 (d, J = 2.0 Hz), 66.1 (d, J = 2.0 Hz),55.2, 55.0, 32.4, 30.0, 16.8, 16.6. 19 F NMR (565 MHz, CDCl3) major: δ = -54.38(s, 3F), minor: -54.51 (s, 3F).GC-MS (EI, m / z, %): C 23 H 19 F3O2, 384.05 (M + .100), 299.10 (55), 191.07 (50). 4-[2-(4-iodophenyl)-2-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3am):

[0103] The NMR data for compound 3am are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.64 (t, J =7.8 Hz, 1H), 7.54-7.51(m, 3H), 7.42-7.38 (m, 4H), 7.32 (t, J = 7.2 Hz, 1H), 7.20 (d, J = 7.8 Hz, 1H),6.95 (d, J = 8.4 Hz, 2H), 6.92 (t, J = 7.8 Hz, 1H), 3.00 (dd, J = 10.8, 8.4 Hz,1H), 2.09 (dd, J = 10.8, 7.8 Hz, 1H), 1.88 (t, J = 7.8 Hz, 1H), minor: 7.78 (t, J = 7.8 Hz, 1H), 7.69 (dt, J = 7.8, 1.2 Hz, 3H), 7.47-7.35 (m, 8H), 7.15 (t, J = 7.8 Hz, 1H), 2.38 (dd, J = 10.2, 7.8 Hz, 1H), 2.15 (t, J = 8.1 Hz, 1H), 2.03(dd, J = 10.2, 7.8 Hz, 1H). 13 C NMR (151 MHz, CDCl3) mixture of diastereomers: δ= 140.7, 140.5, 140.0, 139.5, 138.8, 138.3, 137.5, 137.10, 137.07, 136.6,134.9, 134.1, 130.3, 129.7, 128.8, 128.74, 128.70, 128.4, 128.1, 127.2,127.0, 126.97, 126.9, 126.7, 125.4, 122.2 (q, J = 259.4 Hz), 94.4, 93.6, 67.4(d, J = 1.8 Hz), 65.2 (d, J = 2.0 Hz), 32.4, 30.1, 16.52, 16.48. 19F NMR (565MHz, CDCl3) major: δ = -54.52 (s, 3F), minor: -54.66 (s, 3F).GC-MS (EI, m / z, %): C 22 H 16 F3IO, 479.94 (M + 70), 268.09 (100), 199.03 (45). 2-[2-([1,1'-biphenyl]-4-yl)-1-(trifluoromethoxy)cyclopropyl]naphthalene (3an):

[0104] The NMR data for compound 3an are as follows: 1 H NMR (500 MHz, CDCl3) mixture of diastereomers: 7.89-7.71 (m, 3H), 7.65-6.94 (m, 13H), 3.05-2.43 (m, 1H), 2.19-2.00 (m, 2H). 13 C NMR (151 MHz, CDCl3) mixture of diastereomers: δ = 140.8, 140.4, 139.8, 139.1, 136.8,134.6, 133.8, 133.1, 133.0, 132.9, 132.7, 131.6, 128.93, 128.86, 128.7,128.6, 128.3, 128.15, 128.05, 128.0, 127.7, 127.6, 127.13, 127.10, 127.0,126.9, 126.8, 126.6, 126.53, 126.50, 126.4, 126.1, 124.9, 124.4, 122.3 (q, J = 259.1 Hz), 68.7 (d, J = 1.8 Hz), 66.5 (d, J = 1.8 Hz), 32.2, 30.0, 16.8,16.5. 19 F NMR (565 MHz, CDCl3) major: δ = -54.28 (s, 3F), minor: -54.45 (s, 3F). GC-MS (EI, m / z, %): C 26 H 19F3O, 404.06 (100), 319.13 (M + . 63), 165.07 (47). (E)-4-[2-Styryl-2-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3ao):

[0105] The NMR data of compound 3ao are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.53 (d, J = 7.8 Hz, 2H), 7.48 (d, J = 7.8 Hz, 2H), 7.38 (t, J = 7.8 Hz, 2H), 7.29 (t, J = 7.2 Hz, 1H), 7.21 (d, J = 7.8 Hz, 2H), 7.18 (d, J = 6.6 Hz, 2H), 7.14 (d, J = 7.2 Hz, 3H), 6.61 (d, J = 16.2 Hz, 1H), 5.76 (d, J = 16.8 Hz, 1H), 2.98 (dd, J = 10.5, 7.8 Hz, 1H), 1.91(dd, J = 10.8, 7.2 Hz, 1H), 1.57 (t, J = 7.5 Hz, 1H). 13 C NMR (151 MHz, CDCl3)major: δ = 140.6, 139.8, 136.2, 134.4, 131.7, 129.1, 128.8, 128.5, 127.8,127.3, 127.05, 126.96, 126.4, 124.6, 122.2 (q, J = 258.5 Hz), 66.3 (d, J = 1.7Hz), 30.4, 17.9. 19F NMR (565 MHz, CDCl3) major: δ = -54.20 (s, 3F), minor: -54.85 (s, 3F). GC-MS (EI, m / z, %): C 24 H 19 F3O, 380.10 (M + . 100), 226.08 (55), 91.08 (27). 4-[2-(phenylethynyl)-2-(trifluoromethoxy)cyclopropyl]-1,1'-biphenyl (3ap):

[0106] The NMR data for compound 3ap are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.60 (t, J = 7.8 Hz, 4H), 7.46 (t, J = 7.8 Hz, 2H), 7.38-7.34 (m, 3H), 7.27-7.24 (m, 1H), 7.20 (t, J = 7.5 Hz, 2H),7.14-7.12 (m, 2H), 2.99 (dd, J = 10.8, 8.4 Hz, 1H), 2.02 (dd, J = 10.8, 6.6 Hz, 1H), 1.76 (dd, J = 7.8, 6.6 Hz, 1H). 13 C NMR (151 MHz, CDCl3) major: δ = 140.8,140.2, 134.4, 131.5, 128.9, 128.8, 128.6, 128.2, 127.3, 127.1, 126.9, 122.3(q, J = 260.0 Hz), 121.9, 88.3, ​​83.4, 57.5 (q, J = 2.9 Hz), 31.6, 21.2. 19 F NMR(565 MHz, CDCl3) minor: δ = -56.32 (s, 3F), major: -56.45 (s, 3F).GC-MS (EI,m / z, %): C 24 H 17F3O, 378.03 (M + . 100), 293.09 (55), 129.01 (20). 1-Chloro-4-[2-(4-iodophenyl)-2-(trifluoromethoxy)cyclopropyl]benzene (3aq):

[0107] The NMR data for compound 3aq are as follows: 1 H NMR (600 MHz, CDCl3) major: δ = 7.55 (d, J = 8.4 Hz, 2H), 7.10 (d, J = 8.4 Hz, 2H), 6.95 (d, J = 8.4 Hz, 2H), 6.79 (d, J = 8.4 Hz, 2H), 2.90 (dd, J = 10.8, 8.4 Hz, 1H), 2.05 (dd, J = 10.8, 7.5 Hz, 1H), 1.79 (t, J = 7.8 Hz, 1H). 13 CNMR (151 MHz, CDCl3) major: δ = 137.4, 133.68, 133.66, 132.6, 131.1, 129.3,128.3, 122.1 (q, J = 259.4 Hz), 94.8, 67.6 (d, J = 2.1 Hz), 29.7, 16.4. 19 F NMR(565 MHz, CDCl3) major: δ = -54.62 (s, 3F), minor: -54.76 (s, 3F).GC-MS (EI, m / z , %): C 16 H 11 ClF3IO, 437.77 (M + , 10), 310.93 (100), 191.06 (35). Example 3 Synthesis of trifluoromethoxy-substituted silane compounds Compound 2 was reacted with various hydrosilanes to generate compound 5, specifically as follows: Compound 2 (0.1 mmol), Si(R)3H (0.6 mmol, 6 times the amount), and KO were added sequentially to a dry 5 mL reaction flask (with a built-in magnetic stir bar). t Bu (0.3 mmol, 3 times the volume) and dichloromethane (1.0 mL). Stir at 25 °C for 12 h. After the reaction is complete, add an appropriate amount of dilute hydrochloric acid to quench the reaction. After three extractions with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by silica gel column chromatography using petroleum ether as eluent to obtain a colorless liquid 5.

[0108] The reaction equation is as follows: .

[0109] The specific compounds synthesized are as follows: The synthesis of compound ([1,1'-biphenyl]-4-yl)(trifluoromethoxy)methyltriethylsilane (5a) is as follows: Compound 2a (0.1 mmol), Si(Et)3H (0.6 mmol, 6 times the volume), and KO were added sequentially to a dry 5 mL reaction flask (with a built-in magnetic stirrer). t Bu (0.3 mmol, 3 times the volume) and dichloromethane (1.0 mL). Stir at 25 °C for 12 h. After the reaction is complete, add an appropriate amount of dilute hydrochloric acid to quench the reaction. After three extractions with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by silica gel column chromatography using petroleum ether as eluent to obtain colorless liquid ([1,1'-biphenyl]-4-yl)(trifluoromethoxy)methyltriethylsilane (5a) (23.4 mg, 64%).

[0110] The reaction equation is: .

[0111] The NMR spectrum of compound 5a is as follows: Figure 3 (A is the proton spectrum, B is the carbon spectrum, and C is the fluorine spectrum) As shown, the nuclear magnetic resonance data are: 1 H NMR (500 MHz, CDCl3) δ 7.62 (d, J = 8.0 Hz, 2H), 7.58 (d, J = 7.5 Hz, 2H), 7.46 (t, J = 7.5 Hz, 2H), 7.36 (t, J = 7.2 Hz, 1H), 7.27 (d, J =8.0 Hz,2H), 5.11 (s, 1H), 0.98 (t, J = 7.8 Hz, 9H), 0.72-0.60 (m, 6H). 13 C NMR (151MHz, CDCl3) δ 140.6, 139.4, 138.3, 128.7, 127.2, 127.0, 126.9, 125.5, 122.6(q, J = 256.2 Hz), 75.1 (d, J = 1.5 Hz), 7.0, 1.2. 19 F NMR (565 MHz, CDCl3) δ -58.76 (s, 3F).GC-MS (EI, m / z , %): C 20 H 25 F3OSi, 366.12 (M + , 3), 166.08 (53), 73.04 (100). The synthesis methods for the remaining compounds 5b-5i are the same as those for compound 5a in Example 3, except that the corresponding compound 2 and silane are replaced. The structural formulas and NMR data of the synthesized compounds 5b-5i are as follows: (isopropyl)dimethyl([1,1'-biphenyl]-4-yl(trifluoromethoxy)methyl)silane (5b):

[0112] The NMR data for compound 5b are as follows: 1 H NMR (500 MHz, CDCl3) δ 7.52 (d, J = 7.5 Hz, 2H), 7.48 (d, J = 7.0 Hz, 2H), 7.36 (t, J = 6.8 Hz, 2H), 7.26 (t, J = 7.3 Hz, 1H), 7.16 (d, J = 7.5 Hz, 2H), 4.98 (s, 1H), 0.93-0.83 (m, 7H), -0.00 (d, J = 1.5 Hz, 3H), -0.12 (d, J = 1.5 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 140.6, 139.5, 138.1, 128.8, 127.2,127.0, 126.9, 125.6, 122.6 (q, J = 256.6 Hz), 75.3 (q, J = 1.1 Hz), 17.4, 17.3,11.2, -7.8, -8.0. 19 F NMR (471 MHz, CDCl3) δ -58.65 (s, 3F).GC-MS (EI, m / z, %):C 19 H 23 F3OSi, 352.02 (M + 10), 166.08 (73), 73.04 (100). (tert-butyl)dimethyl([1,1'-biphenyl]-4-yl(trifluoromethoxy)methyl)silane (5c):

[0113] The NMR data for compound 5c are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.48 (d, J = 7.8 Hz, 2H), 7.44 (d, J = 7.8 Hz, 2H), 7.31 (t, J = 7.5 Hz, 2H), 7.21 (t, J = 7.2 Hz, 1H), 7.13 (d, J = 8.4 Hz, 2H), 4.99 (s, 1H), 0.84 (s, 9H), 0.00 (s, 3H), -0.24 (s, 3H). 13 C NMR (151 MHz, CDCl3) δ 140.6, 139.6, 138.3, 128.7, 127.2, 126.92, 126.89, 126.1, 121.8 (q, J = 256.5 Hz), 74.9, 26.6, 17.1, -7.5, -9.0. 19 F NMR (565 MHz, CDCl3) δ -58.13(s, 3F).GC-MS (EI, m / z, %): C 20 H 25F3OSi, 366.04 (M+. 5), 166.09 (53), 73.03(100). (4-tert-butylphenyl)(trifluoromethoxy)methyltriethylsilane (5d):

[0114] The NMR data for compound 5d are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.32 (d, J = 8.4 Hz, 2H), 7.10 (d, J = 8.4Hz, 2H), 5.02 (s, 1H), 1.31 (s, 9H), 0.93 (t, J = 7.8 Hz, 9H), 0.65-0.57 (m,6H). 13 C NMR (151 MHz, CDCl3) δ = 149.5, 135.9, 125.1, 124.8, 122.6 (q, J = 255.8 Hz), 75.2 (d, J = 1.7 Hz), 34.4, 31.4, 7.0, 1.2. 19 F NMR (565 MHz, CDCl3)δ = -58.64 (s).GC-MS (EI, m / z, %): C 18 H 29 F3OSi, 346.12 (M + 3), 137.01 (100), 57.09 (50). Triethyl(p-tolyl(trifluoromethoxy)methyl)silane (5e):

[0115] The NMR data for compound 5e are as follows: 1 H NMR (500 MHz, CDCl3) δ = 7.12 (d, J = 8.0 Hz, 2H), 7.07 (d, J = 8.0Hz, 2H), 5.00 (s, 1H), 2.33 (s, 3H), 0.93 (t, J = 7.8 Hz, 9H), 0.64-0.55 (m,6H). 13C NMR (151 MHz, CDCl3) δ = 136.2, 136.1, 129.0, 125.1, 122.6 (q, J = 255.9 Hz), 75.3 (d, J = (1.7 Hz), 21.1, 7.0, 1.2. 19 F NMR (565 MHz, CDCl3) δ = -58.68 (s, 3F).GC-MS (EI, m / z, %): C 15 H 23 F3OSi, 304.06 (M + 3), 104.08 (95), 87.04 (100). Triethyl[(3-methoxyphenyl)(trifluoromethoxy)methyl]silane (5f):

[0116] The NMR data for compound 5f are as follows: 1 H NMR (500 MHz, CDCl3) δ = 7.23 (t, J = 7.8 Hz, 1H), 6.78-6.73 (m,3H), 5.00 (s, 1H), 3.81 (s, 3H), 0.93 (t, J = 8.0 Hz, 9H), 0.66-0.55 (m, 6H). 13 C NMR (151 MHz, CDCl3) δ = 159.6, 140.9, 129.3, 122.5 (q, J = 256.1 Hz),117.4, 111.8, 110.8, 75.1 (d, J = (2.0 Hz), 55.2, 7.0, 1.2. 19 F NMR (565 MHz, CDCl3) δ = -58.90 (s, 3F). GC-MS (EI, m / z, %): C 15 H 23 F3O2Si, 320.05 (M + 33), 186.04 (50), 87.04 (100). Triethyl[(4-iodophenyl)(trifluoromethoxy)methyl]silane (5g):

[0117] The NMR data for 5g of compound are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.64 (d, J = 8.4 Hz, 2H), 6.93 (d, J = 7.8Hz, 2H), 4.96 (s, 1H), 0.93 (t, J = 7.8 Hz, 9H), 0.61-0.57 (m, 6H). 13 C NMR (151MHz, CDCl3) δ = 139.1, 137.4, 126.9, 122.5 (q, J = 256.5 Hz), 91.6, 74.6 (d, J = 1.8 Hz), 6.9, 1.1. 19 F NMR (565 MHz, CDCl3) δ = -59.02 (s, 3F). GC-MS (EI, m / z, %): C 14 H 20 IF3OSi, 415.92 (M + 3), 289.02 (95), 87.04 (100). Triethyl[(4-bromophenyl)(trifluoromethoxy)methyl]silane (5h):

[0118] The NMR data of compound 5h are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.45 (d, J = 8.4 Hz, 2H), 7.06 (d, J = 8.4Hz, 2H), 4.97 (s, 1H), 0.93 (t, J = 7.8 Hz, 9H), 0.63-0.56 (m, 6H). 13 C NMR (151MHz, CDCl3) δ = 138.4, 131.5, 126.7, 122.5 (q, J = 256.5 Hz), 120.3, 74.5 (d, J = 1.8 Hz), 6.9, 1.1. 19F NMR (565 MHz, CDCl3) δ = -59.01 (s, 3F).GC-MS (EI, m / z, %): C 14 H 20 BrF3OSi, 369.92 (M + 3), 115.07 (50), 87.04 (100). Triethyl[(4-chlorophenyl)(trifluoromethoxy)methyl]silane (5i):

[0119] The NMR data for compound 5i are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.30 (d, J = 8.4 Hz, 2H), 7.12 (d, J = 8.4Hz, 2H), 5.00 (s, 1H), 0.93 (t, J = 8.1 Hz, 9H), 0.63-0.56 (m, 6H). 13 C NMR (151MHz, CDCl3) δ = 137.9, 132.3, 128.5, 126.4, 122.5 (q, J = 256.2 Hz), 74.6 (d, J = 1.7 Hz), 6.9, 1.1. 19 F NMR (565 MHz, CDCl3) δ = -59.00 (s, 3F). GC-MS (EI, m / z, %): C 14 H 20 ClF3OSi, 324.01 (M + 3), 115.07 (43), 87.04 (100). Example 4 Synthesis of trifluoromethoxy-substituted phosphate esters Compound 2 was reacted with tris(ethoxy)phosphine to generate compound 6, specifically by adding compound 2 (0.1 mmol), P(OEt)3 (0.1 mmol, 1 part), and KO to a dry 5 mL reaction flask (with a built-in magnetic stir bar) in sequence. tBu (0.3 mmol, 3 times the volume) and dichloromethane (1.0 mL). After stirring at 25 °C for 40 min, add an appropriate amount of 0.3 mL of water to the reaction system, continue stirring for 1 min, add anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and separate by silica gel column chromatography to obtain white solid 6.

[0120] The reaction equation is as follows: .

[0121] The specific compounds synthesized are as follows: The synthesis of compound [1,1'-biphenyl]-4-yl(trifluoromethoxy)methylphosphonic acid diethyl ester (6a) is as follows: Compound 2a (0.1 mmol), P(OEt)3 (0.1 mmol, 1 volume), and KO were added sequentially to a dry 5 mL reaction flask (with a built-in magnetic stir bar). t Bu (0.3 mmol, 3 times the volume) and dichloromethane (1.0 mL). After stirring at 25 °C for 40 min, 0.3 mL of water was added to the reaction system, and stirring was continued for 1 min. Anhydrous sodium sulfate was added and dried. The mixture was filtered, concentrated under reduced pressure, and separated by silica gel column chromatography to obtain a white solid [1,1'-biphenyl]-4-yl(trifluoromethoxy)methylphosphonic acid diethyl ester (6a) (31.4 mg, 81%).

[0122] The reaction equation is:

[0123] The NMR data for compound 6a are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.63 (d, J = 8.4 Hz, 2H), 7.60 (d, J = 7.2Hz, 2H), 7.55 (dd, J = 8.4, 1.8 Hz, 2H), 7.45 (t, J = 7.8 Hz, 2H), 7.36 (t, J = 7.5 Hz, 1H), 5.36 (d, J = 16.8 Hz, 1H), 4.20-3.96 (m, 4H), 1.31 (t, J = 6.9 Hz, 3H), 1.25 (t, J = 6.9 Hz, 3H). 13 C NMR (151 MHz, CDCl3) δ = 142.1 (d,J = 2.4 Hz), 140.3, 131.4 (d, J = 1.8 Hz), 128.9, 128.0 (d, J = 5.6 Hz), 127.7, 127.3 (d, J =2.0 Hz), 127.1, 121.9 (qd, J = 258.6 Hz, 13.4 Hz), 75.1 (dd, J = 173.7 Hz, 2.0Hz), 64.2 and 63.8 (d, J = 6.9 Hz), 16.4 and 16.2 (d, J = 5.6 Hz). 19 F NMR (565MHz, CDCl3) δ = -59.11 (s, 3F). 31 P NMR (243 MHz, CDCl3) δ 14.66.HRMS (ESI) m / z: calc'd for C 18 H 20 F3O4PNa [M+Na] + 411.0944, found 411.0951. The synthesis methods for the remaining compounds 6b-6h are the same as those for compound 6a in Example 4, only requiring the replacement of the corresponding compound 2. The structural formulas and NMR data of the synthesized compounds 6b-6h are as follows: Diethyl(p-tolyl(trifluoromethoxy)methyl) phosphonate (6b):

[0124] The NMR data for compound 6b are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.36 (dd, J = 8.4, 1.8 Hz, 2H), 7.20 (d, J = 7.8 Hz, 2H), 5.26 (d, J = 16.2 Hz, 1H), 4.16-3.90 (m, 4H), 2.36 (s, 3H), 1.29(t, J = 7.2 Hz, 3H), 1.22 (t, J = 7.2 Hz, 3H). 13C NMR (151 MHz, CDCl3) δ = 139.3(d, J = 3.2 Hz), 129.3 (d, J = 2.1 Hz), 129.27 (d, J = 2.1 Hz), 127.6 (d, J = 5.7Hz), 121.8 (qd, J = 258.3 Hz, 13.9 Hz), 75.2 (dd, J = 174.6 Hz, 2.1 Hz), 64.0and 63.6 (d, J = 6.9 Hz), 21.2, 16.3 and 16.2 (d, J = 5.8 Hz). 19 F NMR (565 MHz, CDCl3) δ = -59.07 (s, 3F). 31 P NMR (243 MHz, CDCl3) δ 14.91.HRMS (ESI) m / z:calc'd for C 13 H 19 F3O4P [M+H] + 327.0968, found 327.0972. Diethyl phosphonate [(4-chlorophenyl)(trifluoromethoxy)methyl] ester (6c):

[0125] The NMR data for compound 6c are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.42 (dd, J = 8.7, 2.1 Hz, 2H), 7.38 (d, J = 8.4 Hz, 2H), 5.26 (d, J = 16.2 Hz, 1H), 4.18-3.95 (m, 4H), 1.30 (t, J = 7.2 Hz, 3H), 1.24 (t, J = 7.2 Hz, 3H). 13 C NMR (151 MHz, CDCl3) δ = 135.3 (d, J = 3.5 Hz), 131.1 (d, J = 1.7 Hz), 128.9 (d,J = 5.7 Hz), 128.9, 121.7 (qd, J = 258.9 Hz, 13.3 Hz), 74.5 (dd, J = 173.5 Hz, 2.0 Hz), 64.2 and 63.8 (d, J = 6.9 Hz), 16.3 (dd, J =15.9 Hz, 5.7 Hz). 19 F NMR (565 MHz, CDCl3) δ = -59.31 (s, 3F). 31 P NMR (243 MHz, CDCl3) δ 14.14.HRMS (ESI) m / z: calc'd for C 12 H 15 ClF3O4PNa [M+Na] + 369.0241, found 369.0249. Diethyl phosphonate [(4-bromophenyl)(trifluoromethoxy)methyl] ester (6d):

[0126] The NMR data for compound 6d are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.53 (d, J = 8.4 Hz, 2H), 7.35 (dd, J = 8.7, 2.1 Hz, 2H), 5.25 (d, J = 16.8 Hz, 1H), 4.18-3.95 (m, 4H), 1.29 (t, J = 7.2 Hz, 3H), 1.24 (t, J = 7.2 Hz, 3H). 13 C NMR (151 MHz, CDCl3) δ = 131.8 (d, J = 2.1 Hz), 131.6 (d, J = 2.0 Hz), 129.2 (d, J = 5.7 Hz), 123.5 (d, J = 3.5 Hz), 121.7 (qd, J = 258.7 Hz, 13.2 Hz), 74.5 (dd, J= 173.5 Hz, 2.3 Hz), 64.2 and 63.8 (d, J = 6.9Hz), 16.3 and 16.2 (d, J = 5.7 Hz). 19 F NMR (565 MHz, CDCl3) δ = -59.33 (s, 3F). 31 P NMR (243 MHz, CDCl3) δ 13.96.HRMS (ESI) m / z: calc'd for C 12 H 16 BrF3O4P [M+H] + 390.9916, found 390.9915. Diethyl phosphonate [(4-iodophenyl)(trifluoromethoxy)methyl] ester (6e):

[0127] The NMR data for compound 6e are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.74 (d, J = 8.4 Hz, 2H), 7.21 (dd, J = 8.4, 2.1 Hz, 2H), 5.23 (d, J = 16.8 Hz, 1H), 4.18-3.96 (m, 4H), 1.30 (t, J = 7.2 Hz, 3H), 1.25 (t, J = 7.2 Hz, 3H). 13 C NMR (151 MHz, CDCl3) δ = 137.8 (d, J = 2.0 Hz), 132.3 (d, J = 2.0 Hz), 129.3 (d, J = 5.7 Hz), 121.7 (qd, J = 258.8 Hz, 13.6 Hz), 95.3 (d, J = 4.1 Hz), 74.6 (dd, J = 173.2 Hz, 2.3 Hz), 64.2 and 63.8 (d, J = 6.9Hz), 16.3 and 16.2 (dd, J = 5.8 Hz).19 F NMR (565 MHz, CDCl3) δ = -59.33 (s, 3F). 31 P NMR (243 MHz, CDCl3) δ 13.94.HRMS (ESI) m / z: calc'd for C 12 H 16 IF3O4P [M+H] + 438.9778, found 438.9777. Diethyl phosphonate [(trifluoromethoxy)(4-trifluoromethylphenyl)methyl] ester (6f):

[0128] The NMR data for compound 6f are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.67 (d, J = 8.4 Hz, 2H), 7.60 (d, J = 6.6Hz, 2H), 5.36 (d, J = 16.8 Hz, 1H), 4.19-4.40 (m, 4H), 1.29 (t, J = 7.2 Hz, 3H), 1.27 (t, J = 7.2 Hz, 3H). 13 C NMR (151 MHz, CDCl3) δ = 136.6, 131.3 (qd, J =32.5, 2.7 Hz), 127.8 (d, J = 5.4 Hz), 125.6-125.5 (m), 123.8 (q, J = 272.3 Hz), 121.7 (qd, J = 259.1 Hz, 13.1 Hz), 74.5 (dd, J = 171.9 Hz, 2.4 Hz), 64.3 and63.9 (d, J = 6.9 Hz), 16.3 and 16.2 (d, J = 5.7 Hz). 19 F NMR (565 MHz, CDCl3) δ = -59.50 (s, 3F), -62.83 (s, 3F). 31P NMR (243 MHz, CDCl3) δ 13.73.HRMS (ESI) m / z:calc'd for C 13 H 16 F6O4P [M+H] + 381.0685, found 381.0692. Diethyl phosphonate [(naphth-2-yl)(trifluoromethoxy)methyl] ester (6g):

[0129] The NMR data for compound 6g are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.94 (t, J = 2.4 Hz, 1H), 7.89-7.85 (m,3H), 7.61 (dt, J = 8.4, 1.8 Hz, 1H), 7.54-7.51 (m, 2H), 5.47 (d, J = 16.2 Hz,1H), 4.18-3.91 (m, 4H), 1.29 (t, J = 7.2 Hz, 3H), 1.21 (t, J = 7.2 Hz, 3H). 13 CNMR (151 MHz, CDCl3) δ = 133.6, 132.9 (d, J = 2.0 Hz), 129.9 (d, J = 2.1 Hz), 128.5 (d, J = 1.8 Hz), 128.2, 127.8, 127.4 (d, J = 7.2 Hz), 126.8, 126.6, 124.7,121.9 (qd, J = 258.7 Hz, 13.6 Hz), 75.5 (dd, J = 173.5 Hz, 2.1 Hz), 64.1 and63.8 (d, J = 6.9 Hz), 16.3 and 16.2 (d, J = 5.9 Hz). 19 F NMR (565 MHz, CDCl3) δ = -59.10 (s, 3F). 31P NMR (243 MHz, CDCl3) δ 14.66.HRMS (ESI) m / z: calc'd forC 16 H 19 F3O4P [M+H] + 363.0968, found 363.0966. Diethyl(3-phenyl-1-(trifluoromethoxy)prop-2-yn-1-yl) phosphonate (6h):

[0130] The NMR data for compound 6h are as follows: 1 H NMR (600 MHz, CDCl3) δ = 7.39-7.35 (m, 5H), 7.06 (d, J = 10.2 Hz,1H), 4.26-4.15 (m, 4H), 1.37 (t, J = 7.2 Hz, 3H), 1.34 (t, J = 7.2 Hz, 3H). 19 FNMR (565 MHz, CDCl3) δ = -58.61 (s, 3F). 31 P NMR (243 MHz, CDCl3) δ 5.45.HRMS(ESI) m / z: calc'd for C 14 H 17 F3O4P [M+H] + 337.0811, found 337.0813. The embodiments described above are merely preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Various modifications and improvements made by those skilled in the art to the technical solutions of the present invention without departing from the spirit of the present invention should fall within the protection scope defined by the claims of the present invention.

Claims

1. The application of an α-trifluoromethoxy carbene reagent in the synthesis of trifluoromethoxy compounds; The general structural formula of the α-trifluoromethoxycarbene reagent is: , The trifluoromethoxy-containing compound is a trifluoromethoxy-substituted silane compound or a trifluoromethoxy-substituted phosphate ester compound; The general structural formula of the silane compounds is: The general structural formula of the phosphate ester compound is: ; The synthesis process is as follows: ； in, R' is one of methyl, ethyl, isopropyl, and tert-butyl, and R” is ethyl; R is one of phenyl, biphenyl, benzyl, isopropylphenyl, tert-butylphenyl, phenoxyphenyl, chlorophenyl, bromophenyl, iodophenyl, trifluoromethylphenyl, nitrophenyl, methoxyphenyl, di-tert-butylphenyl, 1-bromo-2-methoxyphenyl, trimethylphenyl, naphthyl, 2-[4-(adamantane-1-yl)-3-methoxyphenyl]naphth-6-yl, thiophene, nitrofuranyl, alkenylphenyl, chloroalkenylphenyl, alkynylphenyl, propylphenyl, cyclopentyl, and tert-butyl.

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