Beta-trifluoromethyl imine derivative and synthesis method thereof

Abstract

The invention discloses a beta-trifluoromethyl imine derivative and a synthesis method thereof, and belongs to the field of organic synthesis. According to the technical scheme, under the action of an alkali reagent, olefin, diaryl ketimine and a trifluoromethyl-hypervalent iodine (Togni) reagent which are easy to obtain are used as raw materials, an olefin trifluoromethyl amination reaction without participation of transition metal is realized, and a C-C bond and a C-N bond are constructed at the same time under mild conditions. The introduction of trifluoromethyl into organic molecules has significant influence on the physical and chemical properties of compounds, trifluoromethyl amine compounds widely exist in various drug molecules and physiologically active molecules, and the method can efficiently synthesize trifluoromethyl-containing imine compounds, and can be used for synthesis of beta-trifluoromethyl primary amine. Experimental conditions are very mild, experimental operation is simple, convenient and safe, required raw materials are wide in source, and the method has a wide application prospect in the aspect of biological medicine.

Description

Technical Field

[0001] The invention relates to a beta-trifluoromethylimine derivative and a synthesis method thereof, and belongs to the field of organic synthesis. Background Art

[0002] Trifluoromethylamine compounds include α-trifluoromethylamine compounds and β-trifluoromethylamine compounds, among which β-trifluoromethylamine compounds are a class of compounds with important biological significance and play an important role in the field of drug synthesis. The figure below shows a physiologically active molecule with β-trifluoromethyl primary amine.

[0003] Physiologically active molecules represented by β-trifluoromethylamines:

[0004]

[0005] The introduction of trifluoromethyl groups into organic molecules can significantly change the physical and chemical properties of the compounds, and endow them with unique biological activity, high hydrophobicity, lipophilicity and metabolic stability, making them candidate compounds for pesticides and medicines. At present, it is still difficult to directly synthesize β-trifluoromethylamine compounds, especially the extremely challenging β-trifluoromethyl primary amine compounds. However, benzophenone imine is a common precursor for the synthesis of amine compounds, and primary amines can be obtained by hydrolysis. Therefore, β-trifluoromethylimine compounds can be synthesized by controlling the synthesis, and then further hydrolyzed to obtain β-trifluoromethyl primary amine compounds, which have very good application prospects in the synthesis of drug molecules. Summary of the invention

[0006] In view of the above situation, the object of the present invention is to provide a method for synthesizing β-trifluoromethylimine derivatives.

[0007] Another object of the present invention is to provide a method for the trifluoromethyl amination of olefins without the participation of transition metals. The method simultaneously constructs CC bonds and CN bonds under mild conditions and has the advantages of low raw material prices, wide sources, simple and safe experimental operations, and good substrate adaptability.

[0008] Thus, a β-trifluoromethylimine derivative of the present invention has the general formula I:

[0009]

[0010] in:

[0011] R 1 A group selected from substituted and unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, amide, and ester groups;

[0012] R 2Selected from substituted and unsubstituted aryl, heteroaryl, alkyl, hydrogen atom groups;

[0013] R 3 ,R 4 Selected from alkyl groups, hydrogen atoms and other groups;

[0014] The invention provides a method for preparing trifluoromethyl-containing imine derivatives from olefins, which is characterized in that olefins, trifluoromethyl-high-valent iodine (Togni) reagents and diaryl ketone imines are mixed under the conditions of alkali, organic solvent and inert gas atmosphere, reacted at a specified temperature, and finally purified to obtain a product.

[0015] In the synthesis method of the present invention, the general formula of the olefin is II:

[0016]

[0017] in:

[0018] R 1 A group selected from substituted and unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, amide, and ester groups;

[0019] R 2 Selected from substituted and unsubstituted aryl, heteroaryl, alkyl, hydrogen atom groups;

[0020] R 3 ,R 4 Selected from various groups including alkyl and hydrogen atoms.

[0021] In the synthesis method of the present invention, the Togni reagent is one of 3,3-dimethyl-1-(trifluoromethyl)-1,2-benzimidooxolane and 1-(trifluoromethyl)-1,2-benzimidoyl-3(1H)-one. The base is one or more of lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium methoxide, sodium methoxide, potassium methoxide, lithium ethoxide, sodium ethoxide, cesium carbonate, potassium carbonate, sodium carbonate, lithium carbonate, potassium acetate, potassium phosphate, sodium bicarbonate, triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG). The organic solvent is one or more of ethyl acetate, methyl acetate, isopropyl acetate, butyl acetate, γ-butyrolactone, ethylene carbonate, diethyl carbonate, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dichloromethane, 1,2-dichloroethane, dimethyl sulfoxide, n-hexane, cyclohexane, acetone, toluene, xylene, chlorobenzene, tetrahydrofuran, ether, 1,4-dioxane, methanol, ethanol, and isopropanol. The molar ratio of the olefin, Togni reagent, diaryl ketone imine and base is 1.0:1.0-4.0:1.0-4.0:0-4.0; the reaction temperature is 0°C-100°C; the reaction container is in an argon or nitrogen atmosphere; and the reaction time is 0.1-48h.

[0022] The technical solution of the present invention has the following advantages:

[0023] (I) The present invention realizes a three-component reaction of olefins, diaryl ketone imine compounds and trifluoromethyl-high-valent iodine (Togni) reagents under the action of an alkaline reagent in an inert gas atmosphere, completes the trifluoromethyl amination reaction of olefins, and simultaneously constructs a technical solution for CC bonds and CN bonds. The reaction conditions are extremely mild, the raw materials are widely available and cheap, the experimental operation is simple and safe, and the application is easy to expand; (II) trifluoromethylamine compounds are widely present in various drug molecules and physiologically active molecules. This method can efficiently synthesize trifluoromethyl-containing imine compounds, which can be used for the synthesis of β-trifluoromethyl primary amines, and has a foreseeable market commercialization prospect. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 This is a reaction formula of the present invention using α-methylstyrene, benzophenone imine and trifluoromethyl-hypervalent iodine (Togni) reagent as raw materials under standard conditions.

[0025] Figure 1a-12a Proton spectra of some examples, Figure 1b-12b is the carbon spectrum of some examples, Figure 1c-12c Fluorine spectra of some examples. DETAILED DESCRIPTION

[0026] The present invention will now be described in further detail with reference to the following figures. These figures are simplified schematic diagrams, which only illustrate the basic structure of the present invention in a schematic manner, and therefore only show the components related to the present invention:

[0027]

[0028] Examples 1-16

[0029] The following steps are involved:

[0030] (1) adding olefin, diaryl ketone imine, trifluoromethyl-hypervalent iodine (Togni) reagent, base and organic solvent into a reaction vessel;

[0031] (2) In an inert gas atmosphere, the reactants are fully mixed and stirred at a specified temperature for a certain period of time;

[0032] (3) After the reaction is complete, the product is purified.

[0033]

[0034] Embodiment 17

[0035] The following steps are involved:

[0036] (1) adding diaryl ketone, hexamethyldisilazane (HMDS), a catalytic amount of scandium trifluoromethanesulfonate and 1,4-dioxane into a reaction vessel;

[0037] (2) In an inert gas atmosphere, the reactants are fully mixed and stirred at a specified temperature for a certain period of time;

[0038] (3) After removing the solvent under reduced pressure, the steps of Example 1 were carried out to obtain the product.

[0039] The present invention is further described in detail below with reference to the accompanying drawings and embodiments.

[0040] Olefins, benzophenone imine and imine derivatives, trifluoromethyl-hypervalent iodine (Togni) reagent, reaction conditions, reaction products and yields are shown in Tables 1 and 2:

[0041] Table 1: Reactants and reaction conditions in Examples 1-16

[0042]

[0043]

[0044] Table 2: Reactants and reaction conditions in Example 17

[0045]

[0046] The product synthesized in the present invention (Example 1) can be further subjected to the following reaction to prepare a benzoyl-protected β-trifluoromethylamide derivative, which can be used as a new synthesis method for synthesizing β-trifluoromethylamide-containing drug molecules. The reaction equation is:

[0047]

[0048] The NMR data of the products of some embodiments are:

[0049] The NMR data of the product of Example 1 are as follows:

[0050] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.70–7.47 (m, 2H), 7.29–7.24 (m, 1H), 7.24–7.17 (m, 2H), 7.10 (s, 6H),7.04–6.82(m,2H),6.80–5.77(m,2H),3.13–2.96(m,1H),2.73–2.51(m,1H),1.38(s,3H).

[0051] 13 C NMR (101MHz, CDCl3) δ (ppm) = 166.8, 148.0, 141.3, 138.5, 129.9, 128.3, 128.1, 127.9, 12 7.8,127.6,127.4,126.7,126.2(q,J=279.8Hz),126.1,61.4,50.6(q,J=24.7Hz),24.0.

[0052] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.2.

[0053] The NMR data of the product of Example 2 are as follows:

[0054] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.72–7.58 (m, 2H), 7.47–7.35 (m, 4H), 7.35–7.27 (m, 4H), 7.27–7.2 2(m,3H),7.09–6.89(m,2H),4.72(dd,J=9.2,3.3Hz,1H),3.03–2.86(m,1H),2.58–2.44(m,1H).

[0055] 13C NMR (101MHz, CDCl3) δ (ppm) = 168.2, 142.9, 139.6, 136.5, 130.2, 128.68, 128.66, 128.6, 128. 3,128.0,127.6,127.4,126.9,126.1(q,J=278.2Hz),60.8(d,J=2.8Hz),43.0(q,J=26.4Hz).

[0056] 19 F NMR (376MHz, CDCl3) δ (ppm) = -63.4.

[0057] The NMR data of the product of Example 3 are as follows:

[0058] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.81–7.75 (m, 1H), 7.72 (d, J = 8.6Hz, 1H), 7.69–7.63 (m,

[0059] 1H),7.63–7.56(m,2H),7.51–7.41(m,4H),7.39–7.34(m,1H),7.34–7.27(m,2H),7.12–7.04(m,

[0060] 1H), 6.91 (t, J = 7.6Hz, 2H), 6.8–6.0 (m, 2H), 3.30–3.13 (m, 1H), 2.88–2.72 (m, 1H), 1.59 (s, 3H).

[0061] 13 C NMR (101MHz, CDCl3) δ (ppm) = 167.1, 145.0, 141.3, 138.2, 133.0, 132.2, 130.0, 128.4, 128.1,

[0062] 128.0,127.9,127.7,127.4,127.2,126.2(q,J=279.1Hz),126.0,125.8,124.9,124.3,61.6(d,J=2.1

[0063] Hz),50.4(q,J=24.8Hz),24.3.

[0064] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.1.

[0065] The NMR data of the product of Example 4 are as follows:

[0066] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.68–7.53 (m, 2H), 7.41–7.26 (m, 3H), 7.25–7.21 (m, 1H),

[0067] 7.18–6.91(m,4H),6.91–6.78(m,2H),6.78–6.39(m,2H),3.60–3.39(m,1H),3.27–3.08(m,1H),

[0068] 1.80(s,3H).

[0069] 13 C NMR (101MHz, CDCl3) δ (ppm) = 165.6, 141.5, 141.0, 137.5, 133.4, 131.0, 129.9, 128.5, 128.3,

[0070] 128.2,127.9,127.3,127.09,127.07,126.2,126.0(q,J=278.4Hz),62.0(d,J=2.3Hz),45.9(q,J=

[0071] 24.8Hz),26.2.

[0072] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.4.

[0073] The NMR data of the product of Example 5 are as follows:

[0074] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.65–7.54 (m, 2H), 7.39–7.35 (m, 1H), 7.34–7.27 (m, 2H),

[0075] 7.26–7.05(m,7H),6.83–6.32(m,2H),3.19–2.99(m,1H),2.84–2.64(m,1H),1.48(s,3H).

[0076] 13 C NMR (101MHz, CDCl3) δ (ppm) = 167.4, 149.5, 141.0, 138.1, 134.0, 130.1, 129.4, 128.4, 128.0,

[0077] 127.8,127.7,127.4,126.9,126.5,125.9(q,J=279.1Hz),124.5,61.2(d,J=2.3Hz),50.3(q,J=25.1

[0078] Hz),24.2.

[0079] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.2.

[0080] The NMR data of the product of Example 6 are as follows:

[0081] 1 H NMR (400MHz, CDCl3) δ (ppm) = 8.05 (d, J = 8.9Hz, 2H), 7.63–7.53 (m, 2H), 7.42–7.36 (m,

[0082] 3H),7.32(t,J=7.5Hz,2H),7.28–7.20(m,1H),7.12(t,J=7.6Hz,2H),6.75–6.27(m,2H),3.21–

[0083] 2.98(m,1H),2.95–2.67(m,1H),1.56(s,3H).

[0084] 13 C NMR (101MHz, CDCl3) δ (ppm) = 167.9, 154.5, 146.6, 140.6, 138.0, 132.4, 130.4, 130.0, 128.4,

[0085] 128.0,127.6,127.3,125.6(q,J=279.0Hz),123.2,61.4,50.1(q,J=25.3Hz),24.6.

[0086] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.2

[0087] The NMR data of the product of Example 7 are as follows:

[0088] 1H NMR (400MHz, CDCl3) δ (ppm) = 7.55–7.45 (m, 2H), 7.40 (d, J = 8.5Hz, 2H), 7.33–7.28 (m, 1H), 7.27–7.19(m,4H),7.18–7.14(m,1H),7.05(t,J=7.6Hz,2H),6.82–6.07(m,2H),3.10–2.90

[0089] (m,1H),2.86–2.56(m,1H),1.45(s,3H).

[0090] 13 C NMR (101MHz, CDCl3) δ (ppm) = 167.8, 152.5, 140.7, 138.0, 131.8, 130.4, 128.3, 128.0, 127.9, 127. 6,127.5,127.1,125.6(q,J=278.9Hz),118.7,110.6,61.4(d,J=2.2Hz),50.0(q,J=25.4Hz),24.3.

[0091] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.1.

[0092] The NMR data of the product of Example 8 are as follows:

[0093] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.57 (d, J = 7.5Hz, 2H), 7.41–7.35 (m, 1H), 7.35–7.19 (m, 5H) ,7.14(t,J=7.5Hz,2H),7.05(d,J=8.2Hz,2H),6.9–6.0(m,2H),3.20–2.92(m,1H),2.84–

[0094] 2.60(m,1H),1.46(s,3H).

[0095] 13 C NMR (101MHz, CDCl3) δ (ppm) = 167.2, 146.7, 141.1, 138.3, 131.1, 130.1, 128.3, 127.98, 127.95, 127.8, 127.7, 127.5, 125.9 (q, J = 278.9Hz), 120.7, 61.1 (d, J = 2.3Hz), 50.4 (q, J = 24.9Hz), 24.2.

[0096] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.2.

[0097] The NMR data of the product of Example 9 are as follows:

[0098] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.75–7.47 (m, 2H), 7.47–7.26 (m, 3H), 7.21 (t, J = 7.5Hz, 1H), 7.18–6.78(m,6H),6.77–6.27(m,2H),3.22–3.01(m,1H),2.77–2.59(m,1H),2.32(s,3H),

[0099] 1.43(s,3H).

[0100] 13 C NMR (101MHz, CDCl3) δ (ppm) = 166.5, 145.1, 141.4, 138.6, 136.3, 129.8, 128.8, 128.3, 127. 9,127.8,127.6,127.3,126.2(q,J=271.4Hz),125.9,61.3,50.6(q,J=24.2Hz),24.1,21.0.

[0101] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.2.

[0102] The NMR data of the product of Example 10 are as follows:

[0103] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.75–7.65 (m, 2H), 7.41–7.26 (m, 7H), 7.23–7.10 (m, 7H),

[0104] 7.07(t,J=7.6Hz,2H), 6.47(d,J=7.0Hz,2H), 3.11(q,J=10.2Hz,2H).

[0105] 13C NMR (101MHz, CDCl3) δ (ppm) = 168.4, 148.5, 141.7, 138.2, 130.1, 128.5, 127.98, 127.95 ,127.5,127.35,127.29,127.2,126.3,126.1(q,J=279.0Hz),65.0,42.7(q,J=25.8Hz).

[0106] 19 F NMR (376MHz, CDCl3) δ (ppm) = -57.7.

[0107] The NMR data of the product of Example 11 are as follows:

[0108] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.72–7.50 (m, 2H), 7.39 (t, J = 7.2Hz, 1H), 7.32 (t, J = 7.5Hz,

[0109] 2H),7.27–7.24(m,2H),7.24–7.05(m,3H),7.03(dd,J=8.4,2.3Hz,1H),6.78–6.24(m,2H),3.16

[0110] –2.98(m,1H),2.85–2.67(m,1H),1.50(s,3H).

[0111] 13 C NMR (101MHz, CDCl3) δ (ppm) = 167.6, 147.4, 140.8, 138.0, 132.1, 130.8, 130.3, 130.0, 128.43, 128 .38,128.0,127.9,127.6,127.5,125.8,125.7(q,J=278.9Hz),60.9(d,J=2.3Hz),50.1(q,J=25.2

[0112] Hz),24.3.

[0113] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.2.

[0114] The NMR data of the product of Example 12 are as follows:

[0115] 1H NMR (400MHz, CDCl3) δ (ppm) = 7.69–7.50 (m, 2H), 7.46–7.37 (m, 3H), 7.37–7.25 (m, 5H),

[0116] 7.24–7.04(m,5H),2.78–2.56(m,3H),2.49–2.34(m,1H),2.07–1.82(m,2H),1.08(s,3H).

[0117] 13 C NMR (101MHz, CDCl3) δ (ppm) = 164.4, 142.2, 141.4, 139.3, 129.8, 128.4, 128.3, 128.2, 128.0 3,128.01,127.9,126.6(q,J=274.2Hz),125.8,59.8,45.4,45.3(q,J=24.2Hz),30.6,25.5.

[0118] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.3.

[0119] The NMR data of the product of Example 13 are as follows:

[0120] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.64–7.49 (m, 2H), 7.49–7.37 (m, 3H), 7.37–7.32 (m, 1H), 7.3 2–7.26(m,2H),7.26–7.14(m,2H),3.75(d,J=9.4Hz,1H),3.39(d,J=9.4Hz,1H),2.68–2.51

[0121] (m,1H),2.42–2.24(m,1H),1.02(s,3H),0.87(s,9H),0.00(d,J=7.5Hz,6H).

[0122] 13 C NMR (101MHz, CDCl3) δ (ppm) = 165.8, 141.4, 139.6, 129.8, 128.3, 128.2, 128.1, 127.93, 127.87, 126.9(q,J=288.0Hz),69.7,61.5(d,J=1.8Hz),41.3(q,J=25.7Hz),25.8,23.9,18.2,-5.6(d,J=

[0123] 3.2Hz).

[0124] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.3.

[0125] The NMR data of the product of Example 14 are as follows:

[0126] 1 H NMR (400MHz, CDCl3) δ (ppm) = 8.55 (d, J = 6.1Hz, 2H), 7.76–7.58 (m, 2H), 7.50–7.37 (m, 4H), 7 .34(t,J=7.3Hz,2H),7.21(d,J=6.1Hz,2H),6.98(d,J=5.6Hz,2H),4.71(dd,J=9.0,3.6Hz,

[0127] 1H),3.03–2.80(m,1H),2.59–2.43(m,1H).

[0128] 13 C NMR (101MHz, CDCl3) δ (ppm) = 169.8, 151.4, 150.1, 139.0, 136.0, 130.6, 128.8, 128.7, 12 8.5, 128.1, 127.3, 125.7 (q, J = 277.9Hz), 121.9, 59.8 (d, J = 2.9Hz), 42.3 (q, J = 26.7Hz).

[0129] 19 F NMR (376MHz, CDCl3) δ (ppm) = -63.3.

[0130] The NMR data of the product of Example 15 are as follows:

[0131] 1 H NMR (400MHz, CDCl3) δ (ppm) = 10.49 (s, 1H), 7.68 (d, J = 7.3Hz, 2H), 7.63–7.56 (m, 2H), 7.51 –7.35(m,9H),7.31–7.25(m,2H),7.15(t,J=7.3Hz,1H),3.11–2.91(m,1H),2.43–2.27(m,

[0132] 1H),1.35(s,3H).

[0133] 13C NMR (101MHz, CDCl3) δ (ppm) = 172.9, 169.7, 140.7, 137.8, 137.4, 130.9, 129.1, 129.0, 128.40, 128. 37,128.2,127.9,125.4(q,J=278.6Hz),124.3,119.8,63.1(d,J=1.9Hz),41.0(q,J=27.3Hz),26.3.

[0134] 19 F NMR (376MHz, CDCl3) δ (ppm) = -60.7

[0135] The NMR data of the product of Example 16 are as follows:

[0136] 1 H NMR (400MHz, CDCl3) δ (ppm) = 7.58–7.53 (m, 2H), 7.40–7.23 (m, 8H), 7.23–7.08 (m, 3 H),7.01(dd,J=8.0,1.8Hz,2H),3.03–2.88(m,1H),2.85–2.71(m,1H),1.72(s,3H).

[0137] 13 C NMR (101MHz, CDCl3) δ (ppm) = 167.3, 141.2, 137.1, 131.5, 130.1, 128.53, 128.49, 128.4, 128.0, 127.8 ,127.7,127.6,125.8(q,J=278.8Hz),123.0,90.0,87.8,54.4(d,J=2.4Hz),49.0(q,J=25.8Hz),31.1.

[0138] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.9.

[0139] The NMR data of the product of Example 17 are as follows:

[0140] 1H NMR (400MHz, CDCl3) δ (ppm) = 7.56 (d, J = 8.9Hz, 2H), 7.22 (s, 5H), 6.83 (d, J = 9.0Hz, 2H), 6.67–6.60 (m, 2H), 6.46 (d, J=8.1Hz,2H),3.82(s,3H),3.78(s,3H),3.11(dq,J=15.0,11.4Hz,1H),2.69(dq,J=15.1,10.9Hz,1H),1.47(s,3H).

[0141] 13 C NMR (101MHz, CDCl3) δ (ppm) = 166.1, 161.1, 158.8, 148.5, 134.7, 130.9, 130.0, 129.1, 128.1, 126. 6,126.2(d,J=279.2Hz),126.1,113.1,112.7,61.18,61.16,55.3,55.1,50.7(q,J=24.3Hz),24.1.

[0142] 19 F NMR (376MHz, CDCl3) δ (ppm) = -59.2.

[0143] Note: For specific reaction equations and NMR spectra, please see the attached figure in the specification.

[0144] Based on the above ideal embodiments of the present invention, the relevant staff can make various changes and modifications without departing from the technical concept of the present invention through the above description. The technical scope of the present invention is not limited to the contents of the specification, and its technical scope must be determined according to the scope of the claims.

Claims

1. A β-trifluoromethyl imine derivative having the general formula I: in: R 1 A group selected from substituted and unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, amide, and ester groups; R 2 Selected from substituted and unsubstituted aryl, heteroaryl, alkyl, hydrogen atom groups; R 3 ,R 4 Selected from various groups including alkyl and hydrogen atoms.

2. A method for preparing trifluoromethyl-containing primary amine derivatives from olefins, characterized in that: The three components of olefin, diaryl ketone imine and trifluoromethyl-hypervalent iodine (Togni) reagent are fully mixed under the conditions of base, organic solvent and inert gas atmosphere, and then reacted at a specified temperature, and finally separated and purified to obtain the product.

3. The method according to claim 2, characterized in that The trifluoromethyl-hypervalent iodine (Togni) reagent is one of: 3,3-dimethyl-1-(trifluoromethyl)-1,2-benzoiodooxolane and 1-(trifluoromethyl)-1,2-benzidoyl-3(1H)-one.

4. The method according to claim 2, characterized in that: The diaryl ketone imine is: commercially available benzophenone imine or a substituted diaryl ketone imine generated by reacting diaryl ketone with hexamethyldisilazane (HMDS).

5. The method according to claim 2, characterized in that: The base is one or more of lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium methoxide, sodium methoxide, potassium methoxide, lithium ethoxide, sodium ethoxide, cesium carbonate, potassium carbonate, sodium carbonate, lithium carbonate, potassium acetate, potassium phosphate, sodium bicarbonate, triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG).

6. The method according to claim 2, characterized in that The molar ratio of the olefin, trifluoromethyl-togni reagent, diaryl ketone imine and base is 1.0:1.0-4.0:1.0-4.0:0-4.0; the reaction temperature is 0°C-100°C; the reaction container is filled with argon or nitrogen atmosphere; and the reaction time is 0.1-48h.

7. The method according to claim 2, characterized in that The general formula of the olefin is II: in: R 1 A group selected from substituted and unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, amide, and ester groups; R 2 Selected from substituted and unsubstituted aryl, heteroaryl, alkyl, hydrogen atom groups; R 3 ,R 4 Selected from various groups including alkyl and hydrogen atoms.

8. The method according to claim 2, characterized in that: The organic solvent is one or more of ethyl acetate, methyl acetate, isopropyl acetate, butyl acetate, γ-butyrolactone, ethylene carbonate, diethyl carbonate, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dichloromethane, 1,2-dichloroethane, dimethyl sulfoxide, n-hexane, cyclohexane, acetone, toluene, xylene, chlorobenzene, tetrahydrofuran, ether, 1,4-dioxane, methanol, ethanol, and isopropanol.

Images