Reaction method for decarboxylation / cyanoalkylation of cinnamic acid and cyclic ketoxime under catalysis of iron

Abstract

The invention relates to a reaction method for decarboxylation / cyanoalkylation of cinnamic acid and cyclic ketoxime under the catalysis of iron, which comprises the following steps: in a nitrogen atmosphere, taking a cinnamic acid compound and a cyclic ketoxime compound as raw materials, taking iron salt as a catalyst, and reacting for 10-20 hours in a solvent at 90-150 DEG C to prepare far-end cyanoalkyl olefin. The invention provides a simple and effective iron-catalyzed cinnamic acid decarboxylation cyanoalkylation reaction which is used for constructing far-end cyano alkyl olefin taking cyclic ketoxime as a free radical precursor. Compared with the prior art, the method does not need an additional reducing agent, and has good group tolerance. The reaction is suitable for various cyclic ketoxime compounds and cinnamic acid compounds, and corresponding products are provided under mild and neutral redox conditions.

Description

Technical Field

[0001] The present invention relates to a reaction method for iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid and cyclohexanone oxime. Background Art

[0002] Disclosing the information of this background art section is only intended to increase some understanding of the overall background of the present invention, and it is not necessarily regarded as an admission or an implication in any form that this information constitutes the prior art already known to those of ordinary skill in the art.

[0003] Alkyl-substituted olefins are an important part of organic synthesis and are widely present in natural products, pharmaceuticals, pesticides, and organic materials (such as lubricating and protective materials). Among various strategies for constructing alkyl-substituted olefins, transition-metal-catalyzed radical decarboxylative alkylation of α,β-unsaturated carboxylic acids has particularly attracted the attention of chemists because vinyl carboxylic acids are readily available and less toxic. Olefins can be alkylated by radical addition / decarboxylation of alkyl radicals ( Figure 1 ).

[0004] In the past, the reported alkyl radical addition reactions of vinyl carboxylic acids required an external stoichiometric amount of oxidant. In recent years, several redox-neutral radical decarboxylation reactions of α,β-unsaturated carboxylic acids have been developed. However, the direct decarboxylative cyanation reaction of α,β-unsaturated carboxylic acids under a redox-neutral catalytic system is rare. For example, the Duan Xinhua team developed iron-catalyzed radical decarboxylative cyanoalkylation to obtain cyano-substituted olefins from cyclohexanone oxime esters under redox-neutral conditions ( Figure 2 ).

[0005] Despite the existence of this ideal method, the decarboxylative alkylation reaction of unprotected cyclobutanone oxime with α,β-unsaturated carboxylic acids has not been reported so far. On the other hand, distal cyanoalkyl olefins have become attractive functional groups due to their versatility in the conversion to other functional groups. As far as the applicant knows, cyanoalkyl radicals can add to olefins to generate distal cyanoolefins, and there are now many methods to generate cyanoalkyl radicals from cyclohexanone oxime derivatives through transition-metal catalysis, photocatalysis, and electrocatalysis. In addition, in addition to these advances, recent studies have shown that unactivated cyclohexanone oxime can generate distal cyanoalkyl radicals through radical-mediated C-C bond cleavage. Recently, the Yuan Yu group disclosed iron-catalyzed radical-mediated ring-opening alkenylation of cyclohexanone oxime to prepare various distal cyanoalkyl olefins ( Figure 3 ).

[0006] However, the stoichiometric use of reducing agents limits their application in organic synthesis. Summary of the Invention

[0007] In view of the prior art, the present invention studies redox-neutral iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid for the construction of distal cyanoalkyl olefins with cyclohexanone oxime as a radical precursor ( Figure 4 ).

[0008] The technical solution adopted by the present invention is as follows: The present invention provides a reaction method for iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid and cyclohexanone oxime, which method comprises the following steps: Under a nitrogen atmosphere, using a cinnamic acid compound and a cyclohexanone oxime compound as raw materials, an iron salt as a catalyst, reacting at 90-150 °C for 10-20 h in a solvent to prepare a distal cyanoalkyl olefin; Wherein, the cinnamic acid compound is 4-methylcinnamic acid, 3-methylcinnamic acid, 2-methylcinnamic acid, 4-tert-butylcinnamic acid, 4-isopropylcinnamic acid, 4-methoxycinnamic acid, 4-dimethylaminocinnamic acid, 4-fluorocinnamic acid, 3-fluorocinnamic acid, 2-fluorocinnamic acid, 4-chlorocinnamic acid, 3-chlorocinnamic acid, 2-chlorocinnamic acid, 4-bromocinnamic acid, 3-bromocinnamic acid, 2-bromocinnamic acid, 4-trifluoromethylcinnamic acid, 4-cyanocinnamic acid, 4-hydroxycinnamic acid, 4-phenylcinnamic acid, β-naphthylacrylic acid, 5-phenylpentadienoic acid, 2-furylacrylic acid or 2-thiopheneacrylic acid; The cyclohexanone oxime compound is 3-tert-butoxycarbonylcyclobutanone oxime, 3-phenylcyclobutanone oxime, 3-ethoxycarbonylcyclobutanone oxime, 3-benzyloxycyclobutanone oxime, 3-oxetane oxime, 3-thietane oxime, 3-tert-butoxycarbonyl-3-azetidinone oxime, 2-methylcyclopentanone oxime, 2-methyl-3-oxolane oxime or 2-phenylcyclohexanone oxime.

[0009] In one or some embodiments of the present invention, the solvent is dichloromethane (DCM), 1,2-dichloroethane (DCE), 1,4-dioxane (1.4-dioxane), trifluoromethylbenzene (PhCF3), chlorobenzene (PhCl), acetonitrile (MeCN), methyl tert-butyl ether (MTBE), N-methylpyrrolidone (NMP), benzene (Benzene) or toluene (Toluene); preferably chlorobenzene, dichloromethane, 1,2-dichloroethane, trifluoromethylbenzene or N-methylpyrrolidone; more preferably chlorobenzene, dichloromethane, 1,2-dichloroethane, trifluoromethylbenzene; most preferably chlorobenzene.

[0010] In one or some embodiments of the present invention, the molar ratio of the cinnamic acid compound to the cyclohexanone oxime compound is (0.2-5):1; preferably (2-5):1; more preferably (3-5):1; most preferably 3:1.

[0011] In one or some embodiments of the present invention, the iron salt is FeCl2, FeCl3, FeBr2, FeBr3, Fe(OTf)2, Fe(OTf)3, Fe(acac)2, Fe(acac)3, FeI2 or FeSO4; preferably Fe(acac)2, Fe(acac)3, FeCl2, FeSO4, FeBr2 or FeI2; more preferably Fe(acac)2, Fe(acac)3 or FeCl2; most preferably Fe(acac)2.

[0012] In one or some embodiments of the present invention, the reaction temperature is 100~140 °C; preferably 110~130, more preferably 120~130 °C, and most preferably 120 °C.

[0013] In one or some embodiments of the present invention, the ratio of the cinnamic acid compound, the cyclohexanone oxime compound and the solvent is (0.02~0.55) mmol: 0.1 mmol: (0.5~4) mL; preferably (0.2~0.5) mmol: 0.1 mmol: (1~2) mL; more preferably (0.3~0.5) mmol: 0.1 mmol: (1~2) mL; most preferably 0.3 mmol: 0.1 mmol: 2 mL.

[0014] In one or some embodiments of the present invention, the molar ratio of the cinnamic acid compound to the catalyst is 1: (0.05~0.30).

[0015] In one or some embodiments of the present invention, the reaction time is 12~18 h; preferably 14~18 h; more preferably 16~18 h; most preferably 16 h.

[0016] Compared with the related technologies known to the inventors of the present invention, one of the technical solutions of the present invention has the following beneficial effects: The present invention provides a simple and effective iron-catalyzed decarboxylative cyanomethylation reaction of cinnamic acid for constructing distal cyanoalkyl olefins with cyclohexanone oxime as a radical precursor. Compared with the prior art, the present invention does not require an additional reducing agent and has good group tolerance. This reaction is applicable to a variety of cyclohexanone oxime compounds and cinnamic acid compounds and provides the corresponding products under mild and redox-neutral conditions. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] The specification drawings constituting a part of the present invention are used to provide a further understanding of the present invention. The schematic embodiments and descriptions of the present invention are used to explain the present invention and do not constitute an improper limitation of the present invention.

[0018] Figure 1: Radical addition / decarboxylative alkylation of alkenes.

[0019] Figure 2 : Iron-catalyzed radical decarboxylative cyanoalkylation.

[0020] Figure 3 : Iron-catalyzed radical-mediated ring-opening alkenylation of cyclohexanone oxime.

[0021] Figure 4 : Redox-neutral iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid.

[0022] Figure 5 : Substrate scope of the cinnamic acid moiety.

[0023] Figure 6 : Substrate scope of the cyclohexanone oxime moiety.

[0024] Figure 7 : Gram-scale reaction of the present invention. Detailed Description of the Invention

[0025] It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the present invention. Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the technical field to which the present invention belongs.

[0026] It should be noted that the terms used herein are merely for describing specific embodiments and are not intended to limit the exemplary embodiments of the present invention. As used herein, unless the context clearly indicates otherwise, the singular forms are also intended to include the plural forms. In addition, it should be understood that when the terms "comprises" and / or "includes" are used in this specification, they specify the presence of features, steps, operations, and / or combinations thereof.

[0027] In order to enable those skilled in the art to more clearly understand the technical solution of the present invention, the technical solution of the present invention will be described in detail below with reference to specific embodiments.

[0028] Example 1 Screening of Solvents

[0029] Table 1 Screening of Solvents Serial number Solvent Yield (%) 1 Dichloromethane 37 2 Dichloroethane 36 3 1,4-Dioxane 24 4 Trifluoromethylbenzene 35 5 Chlorobenzene 39 6 Acetonitrile 21 7 Methyl tert-butyl ether 21 8 N-Methylpyrrolidone 29 9 Benzene 24 10 Toluene 21 Reaction conditions: Under a nitrogen atmosphere, cinnamic acid 1a (0.1 mmol, 1.0 equiv), cyclobutanone oxime 2a (0.5 mmol, 5.0 equiv), and FeBr2 were reacted in a solvent (2 mL) for 16 h.

[0030] Screening of Solvents (Table 1): When initially screening the reaction conditions, ferrous bromide was selected as the catalyst in this example. The substrate equivalent ratio was 1a:2a = 1:5, and the temperature was 120 о With C as the initial condition, the reaction solvents were screened. In this example, the reaction solvents were first screened, and it was found that all the screened solvents could enable the reaction to proceed smoothly to produce the target product 3a. Among them, using chlorobenzene as the reaction solvent, the reaction yield was the most ideal, reaching 39%. Therefore, chlorobenzene was selected as the reaction solvent in this example.

[0031] Example 2 Screening of Substrate Equivalent Ratio

[0032] Table 2 Screening of Substrate Equivalent Ratio Serial number Ratio Yield (%) 1 1a:2a = 2:1 44 2 1a:2a = 3:1 51 3 1a:2a = 4:1 51 4 1a:2a = 5:1 51 5 1a:2a = 1:2 41 6 1a:2a = 1:3 41 7 1a:2a = 1:4 40 8 1a:2a = 1:5 39 Reaction conditions: Under a nitrogen atmosphere, cinnamic acid 1a, cyclobutanone oxime 2a, and FeBr2 reacted in chlorobenzene (2 mL) for 16 h.

[0033] Screening of Substrate Equivalent Ratio (Table 2): In the second step of this example, the screening of the substrate equivalent ratio was carried out. It was found in this example that increasing the equivalent of cinnamic acid was helpful for improving the reaction yield. When 1a:2a = 3:1, the reaction yield was the best. Continuing to increase the proportion of cinnamic acid, the reaction yield would not increase. Therefore, the equivalent ratio of the substrates was determined as cinnamic acid:cyclobutanone oxime = 3:1 (1a:2a = 3:1) in this example.

[0034] Example 3 Screening of Iron Catalysts

[0035] Table 3 Screening of Iron Catalysts Serial number Fe catalyst Yield (%) 1 <![CDATA[FeCl2]]> 58 2 <![CDATA[FeCl3]]> 41 3 <![CDATA[FeBr2]]> 51 4 <![CDATA[FeBr3]]> 30 5 <![CDATA[Fe(OTf)2]]> 25 6 <![CDATA[Fe(OTf)3]]> 12 7 <![CDATA[Fe(acac)2]]> 70 8 <![CDATA[Fe(acac)3]]> 65 9 <![CDATA[FeI2]]> 48 10 <![CDATA[Fe(NO3)•9H2O]]> ND 11 <![CDATA[FeSO4]]> 53 Reaction conditions: Under a nitrogen atmosphere, cinnamic acid 1a (0.3 mmol, 1.0 equivalent), cyclobutanone oxime 2a (0.1 mmol, 1.0 equivalent), and the iron catalyst reacted in chlorobenzene (2 mL) for 16 h.

[0036] Screening of Catalysts (Table 3): After determining the substrate equivalent ratio, the types of iron catalysts were screened in this example. It was found in this example that except for Fe(NO3)•9H2O, other iron catalysts could enable the reaction to proceed smoothly. In addition, among the screened iron catalysts, the yields of divalent iron were all higher than those of the same type of trivalent iron. Among them, the yield of Fe(acac)2 was the best, reaching 70%. Therefore, Fe(acac)2 was determined as the catalyst in this example.

[0037] Example 4 Screening of Temperature

[0038] Table 4 Temperature screening Serial number <![CDATA[Temperature( о C)]]> Yield (%) 1 90 37 2 100 55 3 110 58 4 120 70 5 130 66 6 140 64 Reaction conditions: Cinnamic acid 1a (0.3 mmol, 3.0 eq.), cyclobutanone oxime 2a (0.1 mmol, 1.0 eq.), and Fe(acac)2 were reacted in chlorobenzene (2 mL) under nitrogen atmosphere for 16 h.

[0039] Temperature screening (Table 4): Afterwards, this example explored the reaction temperature. This example found that whether increasing or decreasing the temperature had a certain effect on the reaction yield, so 120°C was finally used. о C as the reaction temperature.

[0040] Example 5 Concentration screening

[0041] Table 5 Concentration screening Serial number PhCl (mL) Yield (%) 1 0.5 54 2 1.0 59 3 1.5 62 4 2.0 70 Reaction conditions: Cinnamic acid 1a (0.3 mmol, 3.0 eq.), cyclobutanone oxime 2a (0.1 mmol, 1.0 eq.), and FeBr2 were reacted in chlorobenzene for 16 h under nitrogen atmosphere.

[0042] Concentration screening (Table 5): Finally, it was envisioned that reducing the amount of solvent would increase the concentration of the intermolecular reaction and thus improve the reaction yield, but it was ultimately found that reducing the amount of solvent would reduce the reaction yield.

[0043] Next, the optimal reaction conditions for this example were determined as follows: 1a (0.3 mmol), 2a (0.1 mmol), Fe(acac)2 (10 mol%) as catalyst, 2 mL PhCl as solvent, at 120 о C for 16 h.

[0044] Example 6 Substrate expansion After determining the optimal reaction conditions, this example conducted a substrate universality study under the optimal conditions ( Figure 5). First, in this example, attempts were made to introduce some electron-donating groups at the para-position of the benzene ring of cinnamic acid, such as methyl, methoxy, tert-butyl, isopropyl, N,N-dimethylamino, hydroxyl, phenyl (30% - 78%), etc. After the introduction of these substituents, the target product could be obtained in moderate to excellent yields. Subsequently, in this example, some electron-withdrawing groups were introduced at the para-position of the benzene ring of cinnamic acid, such as cyano, trifluoromethyl and other substituents, and the target product could also be obtained in moderate to excellent yields (47% - 63%). In addition, when the benzene ring was substituted with halogen groups, such as fluorine, chlorine, bromine, the target product could be obtained in excellent yields (71% - 75%). In addition to this, this example also tried heterocyclic substrates and found that after replacing the benzene ring with a furan ring or a thiophene ring, the target product could be obtained in excellent yields (82% - 92%).

[0045] After expanding the substrates of the cinnamic acid part, this example further expanded the substrates of the cyclohexanone oxime part ( Figure 6 ). Cyclohexanone oximes substituted with phenyl, ester group, and Boc group had good reaction activities, and the corresponding cyanoalkylation products could be obtained in good to excellent yields (73% - 87%). In addition, this reaction was also applicable to thio-, oxo-, and aza-cyclohexanone oximes, but the yields decreased. Cyclopentanone and cyclohexanone oximes could also react smoothly, but the yields were relatively low (26% - 28%).

[0046] Example 7 Gram-scale reaction To demonstrate the synthetic significance of this method, a gram-scale reaction was carried out in this example ( Figure 7 ). The template reaction was scaled up by 100 times, and finally 1.67 g of the target product (3a) was obtained with a separation yield of 72%.

[0047] It can be seen that the present invention has developed a method for preparing distal nitriles by iron-catalyzed decarboxylation / cyanoalkylation reaction of cinnamic acid with cinnamic acid as a radical acceptor and activator, and converting it into the corresponding cyanoalkylated olefins in good to excellent yields.

[0048] Nuclear magnetic resonance data and mass spectrometry data of the compounds prepared in the above examples:

[0049] 3a: 11H NMR (800 MHz, CDCl3) δ 7.36–7.33 (m, 2H), 7.32–7.29 (m, 2H), 7.23–7.21 (m, 1H), 6.46 (d, J = 15.8 Hz, 1H), 6.13 (dt, J = 15.8, 7.1 Hz, 1H), 2.40–2.37 (q, J = 6.6, 6.0 Hz, 4H), 1.85 (p, J = 7.2 Hz, 2H); 13 13C NMR(200 MHz, CDCl3) δ 137.1, 132.1, 128.6, 127.6, 127.4, 126.1, 119.6, 31.7, 25.0, 16.5; High-resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 14 N + : 172.1121; Measured value: 172.1122.

[0050]

[0051] 3b: 1 1H NMR (800 MHz, CDCl3) δ 7.24 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 7.9 Hz, 2H), 6.43 (d, J = 15.8 Hz, 1H), 6.07 (dt, J = 15.7, 7.1 Hz, 1H), 2.40–2.34 (m, 4H), 2.33 (s, 3H), 1.84 (p, J = 7.2 Hz, 2H); 13 13C NMR (200 MHz, CDCl3) δ 136.9, 134.1, 131.7, 129.1, 126.3, 125.8, 119.4, 31.5, 24.8, 21.0, 16.2; High-resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 13 H 16 N + : 186.1277; Measured value: 186.1279.

[0052]

[0053] 3c: 11H NMR (800 MHz, CDCl3) δ 7.20 (t, J = 7.5 Hz, 1H), 7.17–7.13 (m,2H), 7.05 (t, J = 7.1 Hz, 1H), 6.43 (d, J = 15.8 Hz, 1H), 6.11 (dt, J = 15.7,7.1 Hz, 1H), 2.41–2.34 (m, 4H), 2.34 (s, 3H), 1.84 (p, J = 7.2 Hz, 2H); 13 13C NMR (200 MHz, CDCl3) δ 138.16, 137.05, 132.13, 128.51, 128.17, 127.40,126.83, 123.24, 119.60, 31.69, 25.04, 21.42, 16.44; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 13 H 16 N + : 186.1277; Measured value: 186.1278.

[0054]

[0055] 3d: 1 1H NMR (800 MHz, CDCl3) δ 7.41–7.38 (m, 1H), 7.15 (td, J = 5.7,4.4, 2.5 Hz, 3H), 6.67 (d, J = 15.6 Hz, 1H), 5.99 (dt, J = 15.5, 7.0 Hz, 1H),2.43–2.39 (m, 4H), 2.34 (s, 2H), 1.86 (p, J = 7.2 Hz, 2H); 13 13C NMR (200 MHz,CDCl3) δ 135.00, 133.83, 129.00, 128.69, 127.72, 126.02, 124.82, 124.21,118.29, 30.68, 23.76, 18.55, 15.15; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 13 H 16 N + : 186.1277; Measured value: 186.1278.

[0056]

[0057] 3e: 1 H NMR (800 MHz, CDCl3) δ 7.33 (d, J = 8.3 Hz, 2H), 7.29 (d, J = 8.3 Hz, 2H), 6.44 (d, J = 15.8 Hz, 1H), 6.08 (dt, J = 15.6, 7.1 Hz, 1H), 2.40–2.35 (m, 4H), 1.84 (p, J = 7.2 Hz, 2H), 1.31 (s, 9H); 13 C NMR (200 MHz, CDCl3) δ 150.48, 134.34, 131.81, 126.80, 125.81, 125.53, 119.62, 34.56, 31.68, 31.31, 25.08, 16.40; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 16 H 22 N + : 228.1747; Measured value: 228.1748.

[0058]

[0059] 3f: 1 H NMR (400 MHz, CDCl3) δ 7.30–7.24 (m, 2H), 7.20–7.13 (m, 2H), 6.43 (d, J = 15.8 Hz, 1H), 6.07 (dt, J = 15.8, 7.1 Hz, 1H), 2.88 (hept, J = 6.9 Hz, 1H), 2.41–2.28 (m, 4H), 1.82 (p, J = 7.2 Hz, 2H), 1.24 (d, J = 6.9 Hz, 6H); 13 C NMR (200 MHz, CDCl3) δ 148.24, 134.76, 131.92, 126.70, 126.68, 126.09, 119.64, 33.87, 31.69, 25.10, 23.99, 16.41; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 15 H 20 N+ : 214.1590; Actual value: 214.1591.

[0060]

[0061] 3g: 1 H NMR (800 MHz, CDCl3) δ 7.98 (d, J = 8.3 Hz, 2H), 7.40 (d, J = 8.3 Hz, 2H), 6.50 (d, J = 15.8 Hz, 1H), 6.27 (dt, J = 15.7, 7.0 Hz, 1H), 3.91 (d, J = 7.0 Hz, 3H), 2.45–2.38 (m, 4H), 1.87 (p, J = 7.2 Hz, 2H); 13 C NMR (200MHz, CDCl3) δ 157.84, 130.21, 128.75, 126.02, 124.21, 118.48, 112.82, 54.13, 30.48, 23.95, 15.22; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 13 H 16 NO + : 202.1226; Actual value: 202.1228.

[0062]

[0063] 3h: 1 H NMR (400 MHz, CDCl3) δ 7.22 (d, J = 7.7, 2.4 Hz, 2H), 6.69 (d, J = 7.8, 2H), 6.35 (d, J = 15.8 Hz, 1H), 5.94 - 5.86 (m, 1H), 2.93 (s, 6H), 2.38–2.28 (m, 4H), 1.79 (p, J = 7.2 Hz, 2H); 13 C NMR (200 MHz, CDCl3) δ 149.12, 130.96, 126.12, 124.83, 122.36, 118.95, 111.66, 39.71, 30.88, 24.46, 15.48; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 14 H19 N2 + : 215.1543; Actual value: 215.1541.

[0064]

[0065] 3i: 1 H NMR (800 MHz, CDCl3) δ 7.30 (ddd, J = 8.2, 5.2, 2.4 Hz, 2H), 7.02–6.97 (m, 2H), 6.48 (d, J = 11.5 Hz, 1H), 6.42 (d, J = 15.8 Hz, 1H), 2.41–2.36 (m, 4H), 1.84 (p, J = 7.2 Hz, 2H); 13 C NMR (200 MHz, CDCl3) δ 162.1 (d, J = 246.5 Hz), 133.2 (d, J = 3.3 Hz), 130.9, 127.5 (d, J = 7.9 Hz), 127.3 (d, J = 2.3 Hz), 119.6, 115.5 (d, J = 21.5 Hz), 31.6, 25.0, 16.5; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 13 FN + : 190.1027; Actual value: 190.1029.

[0066]

[0067] 3j: 1 H NMR (800 MHz, CDCl3) δ 7.28–7.24 (m, 1H), 7.10 (d, J = 7.7 Hz, 1H), 7.04 (dt, J = 10.2, 2.0 Hz, 1H), 6.93–6.89 (m, 1H), 6.43 (d, J = 15.8 Hz, 1H), 6.15 (dt, J = 15.7, 7.1 Hz, 1H), 2.42–2.37 (m, 4H), 1.85 (p, J = 7.2 Hz, 2H); 1313C NMR (200 MHz, CDCl3) δ 163.1 (d, J = 245.3 Hz), 139.4 (d, J = 7.7Hz), 131.0 (d, J = 2.6 Hz), 130.0 (d, J = 8.4 Hz), 129.1, 122.0 (d, J = 2.8Hz), 119.4, 114.3, 114.2 (d, J = 21.5 Hz), 114.0, 112.5 (d, J = 21.8 Hz),31.6, 24.9, 16.5; High-resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 13 FN + : 190.1027; Observed value: 190.1027.

[0068]

[0069] 3k: 1 1H NMR (400 MHz, CDCl3) δ 7.41 (td, J = 7.7, 1.7 Hz, 1H), 7.19(tdd, J = 9.2, 5.2, 2.6 Hz, 1H), 7.10–6.98 (m, 2H), 6.60 (d, J = 16.0 Hz,1H), 6.22 (dt, J = 16.0, 7.0 Hz, 1H), 2.43–2.39 (m, 4H), 1.87 (p, J = 7.2 Hz,2H); 13 13C NMR (200 MHz,CDCl3) δ 160.0 (d, J = 248.7 Hz), 130.5 (d, J = 4.8 Hz),128.5 (d, J = 8.4 Hz), 127.2 (d, J = 3.9 Hz), 124.8 (d, J = 12.2 Hz), 124.5(d, J = 3.4 Hz), 124.1 (d, J = 3.5 Hz), 119.5, 115.7 (d, J = 22.2 Hz), 32.1,24.9, 16.5; High-resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 13 FN + : 190.1027; Observed value: 190.1028.

[0070]

[0071] 3l: 1 1H NMR (800 MHz, CDCl3) δ 7.27 (s, 4H), 6.41 (dt, J = 15.8, 1.3 Hz, 1H), 6.11 (dt, J = 15.8, 7.0 Hz, 1H), 2.38 (s, 4H), 1.85 (p, J = 7.2 Hz, 2H); 13 13C NMR (200 MHz, CDCl3) δ 134.72, 132.05, 129.96, 127.84, 127.49, 126.42, 118.60, 30.78, 24.03, 15.62; High-resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 12 H 13 ClN + : 206.0731; Measured value: 206.0733.

[0072]

[0073] 3m: 1 1H NMR (800 MHz, CDCl3) δ 7.33 (t, J = 1.7 Hz, 1H), 7.25–7.18 (m, 3H), 6.41 (d, J = 15.8 Hz, 1H), 6.15 (dt, J = 15.8, 7.1 Hz, 1H), 2.42 - 2.37 (m, 4H), 1.85 (p, J = 7.2 Hz, 2H); 13 13C NMR (200 MHz, CDCl3) δ 138.97, 134.53, 130.76, 129.82, 129.28, 127.30, 125.99, 124.38, 119.45, 31.63, 24.86, 16.51; High-resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 12 H 13 ClN + : 206.0731; Measured value: 206.0731.

[0074]

[0075] 3n: 1 H NMR (800 MHz, CDCl3) δ 7.49 (dd, J = 7.7, 1.3 Hz, 1H), 7.34 (dd, J = 7.9, 1.0 Hz, 1H), 7.24–7.14 (m, 2H), 6.83 (d, J = 15.8 Hz, 1H), 6.12 (dt, J = 15.7, 7.0 Hz, 1H), 2.46–2.40 (m, 4H), 1.88 (p, J = 7.2 Hz, 2H); 13 C NMR(200 MHz, CDCl3) δ 135.26, 132.71, 130.63, 129.67, 128.39, 128.30, 126.84, 126.72, 119.49, 31.85, 24.90, 16.50; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 13 ClN + : 206.0731; Observed value: 206.0732.

[0076]

[0077] 3o: 1 H NMR (800 MHz, CDCl3) δ 7.44–7.41 (m, 2H), 7.21 (d, J = 8.4 Hz, 2H), 6.40 (d, J = 15.8 Hz, 1H), 6.13 (dt, J = 15.8, 7.1 Hz, 1H), 2.41–2.36 (m, 4H), 1.85 (p, J = 7.2 Hz, 2H); 13 C NMR (200 MHz, CDCl3) δ 135.59, 131.21, 130.43, 128.08, 127.19, 120.59, 119.03, 31.22, 24.42, 16.06; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 13 BrN + : 250.0226; Observed value: 250.0227.

[0078]

[0079] 3p: 1 H NMR (800 MHz, CDCl3) δ 7.44–7.41 (m, 2H), 7.21 (d, J = 8.4 Hz, 2H), 6.40 (d, J = 15.8 Hz, 1H), 6.13 (dt, J = 15.8, 7.1 Hz, 1H), 2.41–2.36 (m, 4H), 1.85 (p, J = 7.2 Hz, 2H); 13 C NMR (200 MHz, CDCl3) δ 138.19, 129.58, 129.14, 129.04, 128.26, 127.85, 123.75, 121.71, 118.37, 30.55, 23.79, 15.43; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 13 BrN + : 250.0226; Observed value: 250.0227.

[0080]

[0081] 3q: 1 H NMR (800 MHz, CDCl3) δ 7.55–7.52 (m, 1H), 7.47 (dd, J = 7.8, 1.2 Hz, 1H), 7.27–7.24 (m, 1H), 7.11–7.07 (m, 1H), 6.78 (d, J = 15.7 Hz, 1H), 6.08 (dt, J = 15.6, 7.0 Hz, 1H), 2.43 (qd, J = 7.8, 7.1, 2.3 Hz, 4H), 1.88 (p, J = 7.2 Hz, 2H); 13 C NMR (200 MHz, CDCl3) δ 136.73, 132.58, 130.59, 130.50, 128.37, 127.20, 126.66, 122.96, 119.21, 31.44, 24.56, 16.19; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 13 BrN +: 250.0226; Actual value: 250.0228.

[0082]

[0083] 3r: 1 H NMR (800 MHz, CDCl3) δ 7.56 (d, J = 8.1 Hz, 2H), 7.44 (d, J = 8.1 Hz, 2H), 6.50 (d, J = 15.8 Hz, 1H), 6.25 (dt, J = 15.6, 7.0 Hz, 1H), 2.44–2.39 (m, 4H), 1.87 (p, J = 7.2 Hz, 2H); 13 C NMR (200 MHz, CDCl3) δ 140.6, 130.9, 130.6, 129.3 (q, J = 32.4 Hz), 126.3, 125.6 (q, J = 3.9 Hz), 124.3 (q, J = 271.7 Hz), 119.5, 31.8, 24.9, 16.6; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 13 H 13 F3N + : 240.0995; Actual value: 240.0997.

[0084]

[0085] 3s: 1 H NMR (800 MHz, CDCl3) δ 7.59 (d, J = 8.3 Hz, 2H), 7.42 (d, J = 8.3 Hz, 2H), 6.49 (d, J = 15.8 Hz, 1H), 6.29 (dt, J = 15.8, 7.1 Hz, 1H), 2.46–2.40 (m, 4H), 1.90–1.85 (m, 2H); 13 C NMR (200 MHz, CDCl3) δ 140.11, 131.03, 130.50, 129.17, 125.17, 117.89, 117.56, 109.18, 30.33, 23.27, 15.17; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 13 H 12N2 + : 197.1073; Actual value: 197.1074.

[0086]

[0087] 3t: 1 H NMR (400 MHz, CDCl3) δ 7.25–7.20 (m, 2H), 6.83–6.73 (m, 2H), 6.39 (d, J = 15.8 Hz, 1H), 5.97 (dt, J = 15.8, 7.1 Hz, 1H), 2.41–2.32 (m, 4H), 1.83 (p, J = 7.2 Hz, 4H); 13 C NMR (200 MHz, CDCl3) δ 155.04, 131.40, 130.07, 127.41, 125.36, 119.65, 115.48, 31.64, 25.10, 16.43; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 12 H 14 Nо + : 188.1070; Actual value: 188.1071.

[0088]

[0089] 3u: 1 H NMR (800 MHz, CDCl3) δ 7.61–7.57 (m, 2H), 7.55 (d, J = 8.2 Hz, 2H), 7.45–7.41 (m, 4H), 7.34 (t, J = 7.4 Hz, 1H), 6.50 (d, J = 15.8 Hz, 1H), 6.18 (dt, J = 15.7, 7.0 Hz, 1H), 2.44–2.36 (m, 4H), 1.89–1.82 (m, 2H); 13 C NMR (200 MHz, CDCl3) δ 140.42, 139.86, 135.87, 131.33, 128.55, 127.51, 127.05, 127.02, 126.65, 126.25, 119.31, 31.48, 24.75, 16.20; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 18H 18 N + : 248.1434; Actual value: 248.1433.

[0090]

[0091] 3v: 1 1H NMR (800 MHz, CDCl3) δ 7.78 (dd, J = 12.4, 8.6 Hz, 3H), 7.69 (s,1H), 7.56 (dd, J = 8.5, 1.4 Hz, 1H), 7.47–7.41 (m, 2H), 6.62 (d, J = 15.8 Hz,1H), 6.25 (dt, J = 15.6, 7.0 Hz, 1H), 2.45–2.39 (m, 4H), 1.88 (p, J = 7.2 Hz,2H); 13 13C NMR (200 MHz, CDCl3) δ 134.20, 133.28, 132.52, 131.77, 127.87,127.72, 127.57, 127.32, 125.96, 125.48, 125.44, 123.05, 119.25, 31.44, 24.67,16.13; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 16 H 16 N + : 222.1277; Actual value: 222.1278.

[0092]

[0093] 3w: 1 1H NMR (400 MHz, CDCl3) δ 7.45 – 7.38 (m, 2H), 7.35–7.29 (m, 2H),7.26–7.20 (m, 1H), 7.09–6.71 (m, 1H), 6.54 (dd, J = 34.8, 15.6 Hz, 1H), 6.31–6.25 (m, 1H), 5.76–5.40 (m, 1H), 2.50–2.30 (m, 4H), 1.85–1.77 (m, 2H); 1313C NMR (200 MHz, CDCl3) δ 137.2, 132.6, 131.9, 131.4, 128.6, 127.4, 126.5, 126.2, 119.5, 31.4, 24.9, 16.4; High-resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 14 H 16 N + : 198.1277; Observed value: 198.1279.

[0094]

[0095] 3x: 1 1H NMR (400 MHz, CDCl3) δ 7.32 (d, J = 1.5 Hz, 1H), 6.36 (dd, J = 3.3, 1.8 Hz, 1H), 6.30–6.23 (m, 1H), 6.18 (d, J = 3.3 Hz, 1H), 6.10–6.02 (m, 1H), 2.41–2.33 (m, 4H), 1.89 – 1.79 (m, 2H); 13 13C NMR (200 MHz, CDCl3) δ 152.5, 141.6, 126.4, 120.5, 119.5, 111.2, 107.0, 31.4, 24.9, 16.4 ; High-resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 10 H 12 NO + : 162.0913; Observed value: 162.0915.

[0096]

[0097] 3y: 1 1H NMR (800 MHz, CDCl3) δ 7.12 (d, J = 5.1 Hz, 1H), 6.94 (dd, J = 5.1, 3.5 Hz, 1H), 6.90 (d, J = 3.4 Hz, 1H), 6.58 (d, J = 15.6 Hz, 1H), 5.96 (dt, J = 15.4, 7.1 Hz, 1H), 2.39–2.33 (m, 4H), 1.82 (p, J = 7.2 Hz, 2H); 13CNMR (200 MHz, CDCl3) δ 142.2, 127.4, 127.3, 125.3, 125.0, 123.8, 119.5, 31.5, 24.9, 16.4; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 10 H 12 NS + : 178.0685; Observed value: 178.0686.

[0098]

[0099] 3aa: 1 H NMR (800 MHz, CDCl3) δ 7.36–7.29 (m, 4H), 7.26–7.21 (m, 1H), 6.51 (d, J = 15.7 Hz, 1H), 6.07 (d, J = 15.7 Hz, 1H), 2.79 (q, J = 6.7 Hz, 1H), 2.69–2.53 (m, 4H), 1.47 (s, 9H); 13 C NMR (200 MHz, CDCl3) δ 169.20, 134.78, 132.02, 126.70, 125.73, 124.29, 122.48, 116.03, 80.31, 40.25, 32.72, 26.09, 16.77; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 17 H 22 NO2 + : 271.1645; Observed value: 271.1645.

[0100]

[0101] 3ab: 1 H NMR (800 MHz, CDCl3) δ 7.39–7.34 (m, 2H), 7.31–7.20 (m, 8H), 6.47 (d, J = 15.8 Hz, 1H), 6.07–6.02 (m, 1H), 3.13 (p, J = 7.1 Hz, 1H), 2.72–2.63 (m, 4H); 1313C NMR (200 MHz, CDCl3) δ 141.43, 137.12, 133.19, 129.01, 128.69, 127.63, 127.56, 127.30, 126.31, 126.28, 118.64, 42.14, 38.52, 23.94; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 18 H 18 N + : 248.1434; Measured value: 248.1434.

[0102]

[0103] 3ac: 1 1H NMR (800 MHz, CDCl3) δ 7.35–7.33 (m, 2H), 7.31 (t, J = 7.7 Hz, 2H), 7.24 (t, J = 7.2 Hz, 1H), 6.52 (d, J = 15.7 Hz, 1H), 6.06 (dt, J = 15.4, 7.4 Hz, 1H), 4.25–4.19 (m, 2H), 2.89 (p, J = 6.8 Hz, 1H), 2.74–2.63 (m, 4H), 1.29 (t, J = 7.1 Hz, 3H); 13 13C NMR (200 MHz, CDCl3) δ 171.85, 136.55, 134.14, 128.56, 127.66, 126.24, 124.02, 117.73, 61.48, 41.36, 34.39, 18.51, 14.15; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Theoretical value: C 15 H 18 NO2 + : 244.1332; Measured value: 244.1333.

[0104]

[0105] 3ad: 11H NMR (800 MHz, CDCl3) δ 7.38–7.29 (m, 9H), 7.25–7.22 (m, 1H), 6.52 (d, J = 15.8 Hz, 1H), 6.17–6.11 (m, 1H), 4.66 (d, J = 2.6 Hz, 2H), 3.85–3.81 (m, 1H), 2.65–2.56 (m, 4H); 13 13C NMR (101 MHz, CDCl3) δ 137.40, 136.89, 134.05, 128.59 (d, J = 2.5 Hz), 128.06, 127.88, 127.58, 126.19, 123.82, 74.23, 71.87, 37.37, 22.72; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 19 H 20 NO + : 278.1539; Observed value: 278.1541.

[0106]

[0107] 3ae: 1 1H NMR (800 MHz, CDCl3) δ 7.38 (d, J = 7.4 Hz, 2H), 7.33 (t, J = 7.6 Hz, 2H), 7.27 (d, J = 7.3 Hz, 1H), 6.57 (d, J = 12.9 Hz, 1H), 6.11 (dt, J = 14.7, 6.3 Hz, 1H), 4.17 (d, J = 74.9 Hz, 4H); 13 13C NMR (200 MHz, CDCl3) δ 135.91, 135.36, 128.71, 128.35, 126.71, 123.04, 116.01, 71.71, 54.68; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 11 H 12 NO + : 174.0913; Observed value: 174.1096.

[0108]

[0109] 3af: 11H NMR (800 MHz, CDCl3) δ 7.41–7.39 (m, 2H), 7.34 (t, J = 7.7 Hz, 2H), 7.29–7.27 (m, 1H), 6.58 (d, J = 15.7 Hz, 1H), 6.13 (dt, J = 15.4, 7.6 Hz, 1H), 3.53 (dd, J = 7.6, 1.1 Hz, 2H), 3.25 (s, 2H); 13 13C NMR (200 MHz, CDCl3) δ 134.06, 132.53, 126.83, 126.26, 124.64, 121.07, 114.55, 32.53, 13.59; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 11 H 12 NS + : 190.0685; Measured value: 190.0684.

[0110]

[0111] 3ag: 1 1H NMR (800 MHz, CDCl3) δ 7.38 (d, J = 7.4 Hz, 2H), 7.33 (t, J = 7.6 Hz, 2H), 7.27 (d, J = 7.3 Hz, 1H), 6.57 (d, J = 12.9 Hz, 1H), 6.11 (dt, J = 14.7, 6.3 Hz, 1H), 4.17 (d, J = 74.7 Hz, 4H), 1.52 (s, 9H); 13 13C NMR (200 MHz, CDCl3) δ 136.01, 128.71, 128.16, 126.56, 115.99, 82.12, 41.44, 34.46, 28.26, 28.22; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 16 H 21 N2O2 + : 273.1598; Measured value: 273.1599.

[0112]

[0113] 3ah: 11H NMR (400 MHz, CDCl3) δ 7.38–7.27 (m, 4H), 7.25–7.17 (m, 1H), 6.36 (d, J = 15.9 Hz, 1H), 6.04 (dd, J = 15.9, 8.2 Hz, 1H), 2.41–2.21 (m, 3H), 1.77–1.44 (m, 4H), 1.11 (d, J = 6.7 Hz, 3H); 13 13C NMR (200 MHz, CDCl3) δ 137.39, 135.28, 129.13, 128.55, 127.13, 126.03, 119.72, 36.91, 35.85, 23.38, 20.79, 17.25; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 14 H 18 N + : 200.1434; Observed value: 200.1435.

[0114]

[0115] 3ai: 1 1H NMR (400 MHz, CDCl3) δ 7.39 (dd, J = 8.3, 1.2 Hz, 2H), 7.35–7.30 (m, 2H), 7.28–7.23 (m, 1H), 6.55 (d, J = 16.0 Hz, 0H), 6.09 (dd, J = 16.0, 7.8 Hz, 1H), 4.12–4.01 (m, 1H), 3.73 (dt, J = 9.5, 6.4 Hz, 1H), 3.58 (dt, J = 9.5, 6.4 Hz, 1H), 2.59 (t, J = 6.4 Hz, 2H), 1.36 (d, J = 6.3 Hz, 3H); 13 13C NMR (200 MHz, CDCl3) δ 135.64, 131.39, 130.04, 128.07, 127.36, 125.95, 117.43, 62.20, 21.01, 18.54; High resolution mass spectrometry - electrospray ionization (m / z) [M + H] + Calculated value: C 13 H 16 NO +: 202.1226; Actual value: 202.1229.

[0116] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited by the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications made without departing from the spirit and principle of the present invention shall be equivalent replacement methods and are all included in the protection scope of the present invention.

Claims

1. A reaction method for iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid and cyclohexanone oxime, characterized in that, The method comprises the following steps: Under a nitrogen atmosphere, using a cinnamic acid compound and a cycloalkanone oxime compound as raw materials, and an iron salt as a catalyst, reacting at 90-150 °C for 10-20 h in a solvent to obtain a distal cyanoalkyl olefin; Wherein, the cinnamic acid compound is 4-methylcinnamic acid, 3-methylcinnamic acid, 2-methylcinnamic acid, 4-tert-butylcinnamic acid, 4-isopropylcinnamic acid, 4-methoxycinnamic acid, 4-dimethylaminocinnamic acid, 4-fluorocinnamic acid, 3-fluorocinnamic acid, 2-fluorocinnamic acid, 4-chlorocinnamic acid, 3-chlorocinnamic acid, 2-chlorocinnamic acid, 4-bromocinnamic acid, 3-bromocinnamic acid, 2-bromocinnamic acid, 4-trifluoromethylcinnamic acid, 4-cyanocinnamic acid, 4-hydroxycinnamic acid, 4-phenylcinnamic acid, β-naphthylacrylic acid, 5-phenylpentadienoic acid, 2-furylacrylic acid or 2-thienylacrylic acid; The cycloalkanone oxime compound is 3-tert-butoxycarbonylcyclobutanone oxime, 3-phenylcyclobutanone oxime, 3-ethoxycarbonylcyclobutanone oxime, 3-benzyloxycyclobutanone oxime, 3-oxetane oxime, 3-thietane oxime, 3-tert-butoxycarbonyl-3-azetidinone oxime, 2-methylcyclopentanone oxime, 2-methyl-3-oxolane oxime or 2-phenylcyclohexanone oxime.

2. The reaction method of iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid and cyclohexanone oxime as claimed in claim 1, characterized in that, The solvent is dichloromethane, 1,2-dichloroethane, 1,4-dioxane, trifluoromethylbenzene, chlorobenzene, acetonitrile, methyl tert-butyl ether, N-methylpyrrolidone, benzene or toluene.

3. The reaction method of iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid and cyclohexanone oxime according to claim 2, characterized in that, The solvent is chlorobenzene.

4. The reaction method of iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid and cyclohexanone oxime according to claim 1, characterized in that, The molar ratio of the cinnamic acid compound to the cycloalkanone oxime compound is (0.2-5):

1.

5. The reaction method for the decarboxylation / cyanoalkylation of iron-catalyzed cinnamic acid and cyclohexanone oxime as claimed in claim 1, characterized in that, The catalyst is FeCl2, FeCl3, FeBr2, FeBr3, Fe(OTf)2, Fe(OTf)3, Fe(acac)2, Fe(acac)3, FeI2 or FeSO4.

6. The reaction method for iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid and cyclohexanone oxime according to claim 1, characterized in that, The catalyst is Fe(acac)2.

7. The reaction method for the decarboxylation / cyanoalkylation of iron-catalyzed cinnamic acid and cyclohexanone oxime as claimed in claim 1, characterized in that, The reaction temperature is 100-140 °C.

8. The reaction method for the decarboxylation / cyanoalkylation of iron-catalyzed cinnamic acid and cyclohexanone oxime as claimed in claim 1, characterized in that, The ratio of the cinnamic acid compound, the cycloalkanone oxime compound and the solvent is (0.02-0.55) mmol: 0.1 mmol: (0.5-4) mL.

9. The reaction method for the decarboxylation / cyanoalkylation of iron-catalyzed cinnamic acid and cyclohexanone oxime as claimed in claim 1, wherein The molar ratio of the cinnamic acid compound to the catalyst is 1: (0.05-0.30).

10. The reaction method of iron-catalyzed decarboxylation / cyanoalkylation of cinnamic acid and cyclohexanone oxime according to claim 1, characterized in that, The reaction time is 12-18 h.

Images