Addition product of alkyl radical and capture reagent and addition method and application thereof

Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to an addition product of alkyl free radicals and a capture reagent as well as an addition method and application of the addition product. Dissolving secondary alkyl ethylbenzene A, a capture reagent B, an acridinium salt photocatalyst and an additive into an organic solvent, and carrying out an illumination reaction to obtain an addition product of the alkyl free radical and the capture reagent; wherein the structural general formula of the secondary alkyl ethylbenzene A is # imgabs0 # formula I; the capture reagent B is selected from at least one of # imgabs1 # imgabs2 # TsCN; the structural formula of the addition product of the alkyl free radical and the capture reagent comprises at least one of # imgabs3 #. The invention provides a method for oxidizing secondary alkyl ethylbenzene through single electron transfer to induce the secondary alkyl ethylbenzene to generate carbon-carbon bond breakage and react with a capture reagent to generate a product. Reactants and raw materials are easy to obtain, the reaction process is safe and controllable, the operation is simple, and the production cost is low. And the addition product has high functional group property and is more diversified in application.

Description

Technical Field

[0001] The present application belongs to the technical field of organic synthesis, and in particular relates to an addition product of an alkyl free radical and a capture agent, and an addition method and application thereof. Background Art

[0002] The renaissance of photoredox catalysis has transformed modern radical chemistry. At the center of these advances, alkyl radicals play an integral role in the development of novel synthetic methods under photo / electrochemical catalysis. Typically, alkyl radical precursors undergo single electron transfer, usually with the help of photoredox catalysts, to generate transient alkyl radicals that can participate in various bond-forming processes in a chemo- and stereoselective manner.

[0003] Currently, a large number of alkyl radical precursors have been developed that have a built-in redox group that can close the energy gap between the substrate and the excited state of the photosensitizer. Despite these advances, the generation of alkyl radicals in a precisely controlled manner using common, environmentally benign chemical feedstocks has received little attention. Summary of the invention

[0004] Due to the high oxidation potential of pure alkyl skeletons, the direct generation of alkyl radicals from simple unactivated pure alkyl precursors remains a primary challenge in photoredox catalysis. The purpose of this application is to provide an addition product of an alkyl radical with a capture agent and an addition method and application thereof, aiming to provide a new method for expanding alkyl radical chemistry using secondary alkyl ethylbenzenes.

[0005] In order to achieve the above application purpose, the technical solution adopted in this application is as follows:

[0006] In a first aspect, the present application provides a method for adding an alkyl radical to a capture agent, comprising the following steps:

[0007] Dissolving secondary alkylethylbenzene A, capture agent B, acridinium salt photocatalyst and additives in an organic solvent, and performing a light irradiation reaction to obtain an addition product of an alkyl free radical and the capture agent;

[0008] Wherein, the general structural formula of the secondary alkyl ethylbenzene A is:

[0009] The capture agent B is selected from At least one of TsCN;

[0010] The structural formula of the addition product of the alkyl radical and the capture agent includes: At least one of;

[0011] Among them, R 1 , R2 R is independently selected from the same or different alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, heteroalkenyl, alkoxy, fluorocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkynyl, heteroalkynyl, cycloalkynyl, heterocycloalkynyl, aryl, substituted aryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl, alkenylalkyl, alkynylalkyl, cyanoalkyl, alkyloxycarbonylalkyl, silylalkyl, halogen, trifluoromethoxy, sulfonamide, heterocyclic aryl, and hydrogen atom; 3 , R 4 , R 5 , R 6 Each of them is independently selected from the same or different ester group, alkyl group, heteroalkyl group, hydrogen atom, benzenesulfonyl group, aryl group, alkyl-substituted aryl group and alkoxy group.

[0012] In a second aspect, the present application provides an addition product of an alkyl radical and a capture agent obtained by the above method, wherein the structural formula of the addition product of the alkyl radical and the capture agent includes: At least one of; wherein R 1 , R 2 R is independently selected from the same or different alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, heteroalkenyl, alkoxy, fluorocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkynyl, heteroalkynyl, cycloalkynyl, heterocycloalkynyl, aryl, substituted aryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl, alkenylalkyl, alkynylalkyl, cyanoalkyl, alkyloxycarbonylalkyl, silylalkyl, halogen, trifluoromethoxy, sulfonamide, heterocyclic aryl, and hydrogen atom; 6 Any one selected from an ester group, an alkyl group, a heteroalkyl group, a hydrogen atom, a benzenesulfonyl group, an aryl group, an alkyl-substituted aryl group, and an alkoxy group.

[0013] In a third aspect, the present application provides an application of the addition product prepared by the above addition method or the addition product of the above alkyl free radical and a capture agent at least in the synthesis of drug intermediates, the preparation of functional materials or the preparation of chiral ligands.

[0014] The first aspect of the present application provides a method for the addition of alkyl radicals and capture agents, which is oxidized by single electron transfer, and then induces carbon-carbon bond cleavage of secondary alkyl ethylbenzene A by proton coupled electron transfer (PCET), and then reacts with capture agent B to generate an addition product of alkyl radicals and capture agents. Among them, acridine salt photocatalysts have a high oxidation potential and can oxidize neutral benzene rings, thereby promoting the reaction. A method for generating alkyl radicals from linear unactivated secondary alkyl ethylbenzene is realized, and a carbon-carbon bond cleavage method of secondary alkyl ethylbenzene that has not been realized before is realized, and the substrate range is relatively wide. These substrates are easily oxidized by acridine salt photocatalysts under blue LED irradiation, and then accept nucleophilic attack to construct core alcohol intermediates. The resulting alcohol can be oxidized to alkoxy radicals, selectively undergoing β-cleavage to deliver alkyl radicals that can be accepted by various nucleophilic agents. This method represents a new method for expanding alkyl radical chemistry using secondary alkyl ethylbenzene. The generated alkyl radicals can be captured by a variety of capture agents, including electron-deficient double bonds, heterocycles, toluenesulfonyl cyanide, etc. In addition, the reactant raw materials are easy to obtain, and the reactants do not need to be additionally modified before the reaction, and can be directly used for preparation and production. The reaction process is safe and controllable, the operation steps are simplified, and the reaction route is shortened; the production cost of preparing such captured addition products is significantly reduced, and the designability and application prospects of such compounds are greatly expanded. In addition, the addition products obtained by this method have high functionality, making them more diversified in the synthesis of drug intermediates, functional materials and metal ligands. They can be widely used in the synthesis of drug intermediates, the preparation of chiral ligands and functional materials, and can effectively reduce the economic cost of preparing drug intermediates and functional materials, and provide their environmental friendliness.

[0015] The addition product of the alkyl free radical and the capture agent provided in the second aspect of the present application has high functionality and can be widely used in the fields of organic synthetic chemistry, biochemistry, asymmetric catalysis, pesticide and pharmaceutical research, such as in the synthesis of drug intermediates, the preparation of functional materials, and the preparation of chiral ligands such as metal ligands.

[0016] The addition product of the above-mentioned alkyl free radical and the capture agent provided in the third aspect of the present application can provide raw materials or reaction intermediates for the synthesis of drug intermediates, the preparation of functional materials or the preparation of chiral ligands due to its high functionality; it can provide diversified choices for the synthesis of drug intermediates, functional materials and applications. DETAILED DESCRIPTION

[0017] In order to make the technical problems, technical solutions and beneficial effects to be solved by the present application more clearly understood, the present application is further described in detail below in conjunction with the embodiments. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application.

[0018] In this application, the term "and / or" describes the association relationship of associated objects, indicating that there may be three relationships. For example, A and / or B can mean: A exists alone, A and B exist at the same time, and B exists alone. A and B can be singular or plural. The character " / " generally indicates that the associated objects are in an "or" relationship.

[0019] In this application, "at least one" means one or more, and "plurality" means two or more. "At least one of the following" or similar expressions refers to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b or c", or "at least one of a, b and c", can all represent: a, b, c, ab (i.e. a and b), ac, bc, or abc, where a, b, c can be single or multiple, respectively.

[0020] It should be understood that in the various embodiments of the present application, the size of the serial numbers of the above-mentioned processes does not mean the order of execution, some or all of the steps can be executed in parallel or sequentially, and the execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of the present application.

[0021] The terms used in the embodiments of the present application are only for the purpose of describing specific embodiments, and are not intended to limit the present application. The singular forms "a", "an" and "the" used in the embodiments of the present application and the appended claims are also intended to include plural forms, unless the context clearly indicates other meanings.

[0022] The weight of the relevant components mentioned in the embodiments of the present specification can not only refer to the specific content of each component, but also represent the proportional relationship between the weights of the components. Therefore, as long as the content of the relevant components in the embodiments of the present specification is proportionally enlarged or reduced, it is within the scope disclosed in the embodiments of the present specification. Specifically, the mass in the embodiments of the present specification can be μg, mg, g, kg and other mass units known in the chemical industry.

[0023] The terms "first" and "second" are used only for descriptive purposes to distinguish objects such as substances from each other, and should not be understood as indicating or implying relative importance or implicitly indicating the number of indicated technical features. For example, without departing from the scope of the embodiments of the present application, the first XX may also be referred to as the second XX, and similarly, the second XX may also be referred to as the first XX. Thus, the features defined as "first" and "second" may explicitly or implicitly include one or more of the features.

[0024] The term "alkyl" refers to a straight or branched, monovalent, saturated aliphatic chain, including but not limited to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl and other similar groups.

[0025] "Hydrocarbon group", the minimum and maximum carbon content of the hydrocarbon group is indicated by a prefix, for example, the prefix (C a -C b )alkyl refers to any alkyl group containing from "a" to "b" carbon atoms. Thus, for example, (C1-C6)alkyl refers to an alkyl group containing from one to six carbon atoms.

[0026] "Alkoxy" refers to a straight or branched, monovalent, saturated aliphatic chain bonded to an oxygen atom, including but not limited to methoxy, ethoxy, propoxy, butoxy, isobutoxy, tert-butoxy and other similar groups. (C a -C b ) Alkoxy refers to any straight or branched, monovalent, saturated aliphatic chain containing an alkyl group of "a" to "b" carbon atoms and bonded to an oxygen atom.

[0027] "Heteroalkyl" refers to a linear or branched, monovalent, saturated aliphatic chain attached to at least one heteroatom, such as, but not limited to, methylaminoethyl or other similar groups.

[0028] "Alkenyl" refers to straight or branched chain hydrocarbons having one or more double bonds, including but not limited to ethenyl, propenyl, and other similar groups.

[0029] "Heteroalkenyl" refers to a straight or branched hydrocarbon chain having one or more double bonds attached to at least one heteroatom, including but not limited to vinylaminoethyl or other similar groups.

[0030] "Alkynyl" refers to straight or branched chain hydrocarbons having one or more triple bonds, including but not limited to ethynyl, propynyl, and other similar groups.

[0031] "Heteroalkynyl" refers to a straight or branched chain hydrocarbon having one or more triple bonds attached to at least one heteroatom, including but not limited to ethynyl, propynyl and other similar groups.

[0032] "Aryl" refers to a cyclic aromatic hydrocarbon, including but not limited to phenyl, naphthyl, anthracenyl, phenanthrenyl and other similar groups.

[0033] "Heteroaryl" refers to a monocyclic or polycyclic or condensed aromatic hydrocarbon in which one or more carbon atoms have been replaced by heteroatoms such as nitrogen, oxygen or sulfur. If the heteroaryl contains more than one heteroatom, these heteroatoms may be the same or different. Heteroaryl groups include, but are not limited to, benzofuranyl, benzothiophenyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzopyranyl, furanyl, imidazolyl, indazolyl, indolizinyl, indolyl, isobenzofuranyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthyridinyl, oxadiazolyl, oxazinyl, oxazolyl, phthalazinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridin[3,4-b]indolyl, pyridyl, pyrimidinyl, pyrrolyl, quinolizinyl, quinolyl, quinoxalinyl, thiadiazolyl, thiatriazolyl, thiazolyl, thienyl, triazinyl, triazolyl, xanthenyl and other similar groups.

[0034] "Cycloalkyl" refers to a saturated monocyclic or polycyclic alkyl group, which may be fused with an aromatic hydrocarbon group. Cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, indanyl, tetrahydronaphthyl and other similar groups.

[0035] "Heterocycloalkyl" refers to a saturated monocyclic or polycyclic alkyl group, which may be fused to an aromatic hydrocarbon group, in which at least one carbon atom has been replaced by a heteroatom such as nitrogen, oxygen or sulfur. If the heterocycloalkyl group contains more than one heteroatom, these heteroatoms may be the same or different. Heterocycloalkyl includes, but is not limited to, azepanyl, azetidinyl, dihydroindole, morpholinyl, piperazinyl, piperidinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydroquinolinyl, tetrahydroindazolyl, tetrahydroindolyl, tetrahydroisoquinolinyl, tetrahydropyranyl, tetrahydroquinoxalinyl, tetrahydrothiopyranyl, thiazolidinyl, thiomorpholinyl, thioxanthenyl, thioxanthyl and other similar groups.

[0036] "Cycloalkenyl" refers to an unsaturated, monocyclic or polycyclic alkenyl group having one or more double bonds, which may be fused to an aromatic hydrocarbon group, including but not limited to cyclovinyl, cyclopropenyl or other similar groups.

[0037] "Heterocycloalkenyl" refers to an unsaturated, monocyclic or polycyclic alkenyl group with one or more double bonds, which may be fused to an aromatic hydrocarbon group, and in which at least one carbon atom is replaced by a heteroatom such as nitrogen, oxygen or sulfur. If the heterocycloalkyl group contains more than one heteroatom, these heteroatoms may be the same or different.

[0038] "Cycloalkynyl" refers to an unsaturated, monocyclic or polycyclic alkynyl group having one or more triple bonds, which may be fused to an aromatic hydrocarbon group, including but not limited to cycloethynyl, cyclopropynyl or other similar groups.

[0039] "Heterocycloalkynyl" refers to an unsaturated, monocyclic or polycyclic alkynyl group with one or more triple bonds, which may be fused to an aromatic hydrocarbon group, and in which at least one carbon atom is replaced by a heteroatom such as nitrogen, oxygen or sulfur. If the heterocycloalkyl group contains more than one heteroatom, these heteroatoms may be the same or different.

[0040] A first aspect of an embodiment of the present application provides a method for adding an alkyl radical to a capture agent, comprising the following steps:

[0041] S10. dissolving the secondary alkylethylbenzene A, the capture agent B, the acridinium salt photocatalyst and the additive in an organic solvent, and performing a light irradiation reaction to obtain an addition product of the alkyl radical and the capture agent;

[0042] Among them, the general structural formula of secondary alkyl ethylbenzene A is:

[0043] Capture reagent B is selected from At least one of TsCN (p-toluenesulfonyl nitrile);

[0044] The structural formulas of the addition products of alkyl radicals and capture agents include: At least one of;

[0045] Among them, R 1 , R 2 R is independently selected from the same or different alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, heteroalkenyl, alkoxy, fluorocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkynyl, heteroalkynyl, cycloalkynyl, heterocycloalkynyl, aryl, substituted aryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl, alkenylalkyl, alkynylalkyl, cyanoalkyl, alkyloxycarbonylalkyl, silylalkyl, halogen, trifluoromethoxy, sulfonamide, heterocyclic aryl, and hydrogen atom; 3 , R 4 , R 5 , R 6 Each of them is independently selected from the same or different ester group, alkyl group, heteroalkyl group, hydrogen atom, benzenesulfonyl group, aryl group, alkyl-substituted aryl group and alkoxy group.

[0046] The addition method of alkyl radicals and capture agents provided in the first aspect of the embodiment of the present application, through single electron transfer, oxidation of secondary alkyl ethylbenzene A, and subsequent proton coupled electron transfer (PCET) to induce carbon-carbon bond cleavage, and then react with capture agent B to generate addition products of alkyl radicals and capture agents. Among them, acridinium salt photocatalysts have a high oxidation potential and can oxidize neutral benzene rings, thereby promoting the reaction. The addition method of alkyl radicals and capture agents provided in the embodiment of the present application realizes a method for generating alkyl radicals from linear unactivated secondary alkyl ethylbenzene, realizes a previously unrealized carbon-carbon bond cleavage method for secondary alkyl ethylbenzene, and has a wide range of substrates. These substrates are easily oxidized by acridinium salt photocatalysts under blue LED irradiation, and then accept nucleophilic attack to construct core alcohol intermediates. The resulting alcohol can be oxidized to alkoxy radicals, selectively undergoing β-cleavage to deliver alkyl radicals that can be accepted by various nucleophilic agents. This method represents a new method for expanding alkyl radical chemistry using secondary alkyl ethylbenzene. The generated alkyl radicals can be captured by a variety of capture agents, including electron-deficient double bonds, heterocycles, toluenesulfonyl cyanide, etc. In addition, the reactant raw materials are easy to obtain, and the reactants do not need to be additionally modified before the reaction, and can be directly used for preparation and production. The reaction process is safe and controllable, the operation steps are simplified, and the reaction route is shortened; the production cost of preparing such captured addition products is significantly reduced, and the designability and application prospects of such compounds are greatly expanded. In addition, the addition products obtained by this method have high functionality, making them more diversified in the synthesis of drug intermediates, functional materials and metal ligands. They can be widely used in the synthesis of drug intermediates, the preparation of chiral ligands and functional materials, and can effectively reduce the economic cost of preparing drug intermediates and functional materials, and provide their environmental friendliness.

[0047] In some embodiments, the secondary alkylethylbenzene A and the capture reagent B in step S10 can be prepared by referring to existing preparation methods, or can be directly purchased from the market. The reactant raw materials are easy to obtain, and the reactants do not need to be additionally modified before the reaction, and can be directly used for preparation and production, which simplifies the operation steps, shortens the reaction route, and reduces the preparation and production costs.

[0048] In some embodiments, the molar ratio of the acridinium salt photocatalyst, additive, secondary alkylethylbenzene A and capture agent B is (0.1-20):(0.1-20):(0.2-40):(1-100); this ratio is conducive to the full and thorough addition reaction, reduces the formation of by-products, and improves the purity of the product.

[0049] In some embodiments, the conditions of the light irradiation reaction include: reacting in an inert atmosphere with an irradiation wavelength of 400nm to 480nm for 24 to 48h. Under such reaction conditions, it is more conducive to promoting the oxidation of neutral benzene rings by acridinium salt photocatalysts, oxidizing secondary alkyl ethylbenzene A through single electron transfer, thereby inducing the cleavage of carbon-carbon bonds, and then reacting with the capture agent B to generate an addition product of alkyl free radicals and the capture agent.

[0050] In some embodiments, in the addition product of secondary alkylethylbenzene A and alkyl radical and capture agent, R 1 , R 2 are independently selected from the same or different C1-C 20 Alkyl, C1-C 20 Heteroalkyl, C3-C 20 Cycloalkyl, C3-C 20 Heterocycloalkyl, C2-C 20 Alkenyl, C2-C 20 Heteroalkenyl, C3-C 20 Cycloalkenyl, C3-C 20 Heterocycloalkenyl, C2-C 20 Alkynyl, C2-C 20 Heteroalkynyl, C3-C 20 Cycloalkynyl, C3-C 20 Heterocycloalkynyl, C1-C 20 Alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, aryl (C1-C 20 ) alkyl, heteroaryl (C1-C 20 ) alkyl, C2-C 20 Alkenyl (C1-C 20 ) alkyl, C2-C 20 Alkynyl (C1-C 20 ) alkyl, cyano (C1-C 20 ) alkyl, alkyloxy, carbonylalkyl, silylalkyl C3-C 20 , halogen, trifluoromethoxy, sulfonamide, or hydrogen atom.

[0051] In some embodiments, in the addition product of secondary alkylethylbenzene A and alkyl radical and capture agent, R 1 , R 2 are independently selected from the same or different C1-C 10 Alkyl, C1-C 10 Heteroalkyl, C3-C 10 Cycloalkyl, C3-C 10 Heterocycloalkyl, C2-C 10 Alkenyl, C2-C 10 Heteroalkenyl, C3-C 10Cycloalkenyl, C3-C 10 Heterocycloalkenyl, C2-C 10 Alkynyl, C2-C 10 Heteroalkynyl, C3-C 10 Cycloalkynyl, C3-C 10 Heterocycloalkynyl, C1-C 10 Alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, aryl (C1-C 10 ) alkyl, heteroaryl (C1-C 10 ) alkyl, C2-C 10 Alkenyl (C1-C 10 ) alkyl, C2-C 10 Alkynyl (C1-C 10 ) alkyl, cyano (C1-C 10 ) alkyl, alkyloxy, carbonylalkyl, silylalkyl C3-C 10 , halogen, trifluoromethoxy, sulfonamide, or hydrogen atom.

[0052] In some embodiments, in the addition product of secondary alkylethylbenzene A and alkyl radical and capture agent, R 1 , R 2 are independently selected from the same or different C1-C5 alkyl, C1-C5 heteroalkyl, C3-C5 cycloalkyl, C3-C5 heterocycloalkyl, C2-C5 alkenyl, C2-C5 heteroalkenyl, C3-C5 cycloalkenyl, C3-C5 heterocycloalkenyl, C2-C5 alkynyl, C2-C5 heteroalkynyl, C3-C5 cycloalkynyl, C3-C5 heterocycloalkynyl, C1-C5 alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, aryl (C1-C 20 )alkyl, heteroaryl (C1-C5)alkyl, C2-C5 alkenyl (C1-C5)alkyl, C2-C5 alkynyl (C1-C5)alkyl, cyano (C1-C5)alkyl, alkyloxy, carbonylalkyl, silylalkyl C3-C5, halogen, trifluoromethoxy, sulfonamide, hydrogen atom.

[0053] In some embodiments, the heterocycle includes any of quinoline, pyridine, thiazole, benzothiazole, pyrazine, pyrimidine, purine.

[0054] In some embodiments, in the addition product of the capture agent B and the alkyl radical and the capture agent, R 3 , R 4 , R 5 , R 6 are independently selected from the same or different ester groups, C1-C 20 Alkyl, C1-C 20 Heteroalkyl, hydrogen atom, benzenesulfonyl, aryl, C1-C20 Alkyl substituted aryl, C1-C 20 Any of the alkoxy groups.

[0055] In some embodiments, in the addition product of the capture agent B and the alkyl radical and the capture agent, R 3 , R 4 , R 5 , R 6 are independently selected from the same or different ester groups, C1-C 10 Alkyl, C1-C 10 Heteroalkyl, hydrogen atom, benzenesulfonyl, aryl, C1-C 10 Alkyl substituted aryl, C1-C 10 Any of the alkoxy groups.

[0056] In some embodiments, in the addition product of the capture agent B and the alkyl radical and the capture agent, R 3 , R 4 , R 5 , R 6 Each of them is independently selected from the same or different ester group, C1-C5 alkyl group, C1-C5 heteroalkyl group, hydrogen atom, benzenesulfonyl group, aryl group, C1-C5 alkyl substituted aryl group, and C1-C5 alkoxy group.

[0057] In some embodiments, C1-C 20 The alkyl group may be (C1-C 10 )alkyl, (C1-C5)alkyl, (C1-C4)alkyl, (C1-C3)alkyl, (C1-C2)alkyl, etc. In some specific embodiments, (C1-C 20 ) The alkyl group may specifically be methyl, ethyl, propyl, butyl, isobutyl, pentyl, isopentyl, or the like.

[0058] In some embodiments, (C1-C 20 ) heteroalkyl can be (C1-C 10 ) heteroalkyl, (C1-C5) heteroalkyl, (C1-C4) heteroalkyl, (C1-C3) heteroalkyl, (C1-C2) heteroalkyl, etc. In some specific embodiments, the heteroatom can be a halogen, a nitrogen atom, a sulfur atom, etc.

[0059] In some embodiments, (C3-C 20 ) Cycloalkyl can be (C3-C 10 )cycloalkyl, (C3-C5)cycloalkyl, (C3-C4)cycloalkyl, etc. In some specific embodiments, (C3-C 20 ) The cycloalkyl group may be cyclopropyl, cyclobutyl, cyclopentyl, etc.

[0060] In some embodiments, (C3-C20 )Heterocycloalkyl may be (C3-C 10 )heterocycloalkyl, (C3-C 10 ) heterocycloalkyl, (C3-C5) heterocycloalkyl, (C3-C4) heterocycloalkyl, etc. In some specific embodiments, the heteroatom can be a halogen, a nitrogen atom, a sulfur atom, etc.

[0061] In some embodiments, (C2-C 20 )Alkenyl may be (C3-C 10 )alkenyl, (C3-C5)alkenyl, (C3-C4)alkenyl, (C2-C3)alkenyl, etc. In some specific embodiments, (C2-C 20 )Alkenyl may be ethenyl, propenyl, butenyl, pentenyl, etc.

[0062] In some embodiments, (C2-C 20 ) heteroalkenyl can be (C2-C 10 )heteroalkenyl, (C3-C 10 ) heteroalkenyl, (C3-C5) heteroalkenyl, (C3-C4) heteroalkenyl, (C2-C3) heteroalkenyl, etc. In some specific embodiments, the heteroatom can be a halogen, a nitrogen atom, a sulfur atom, etc.

[0063] In some embodiments, (C3-C 20 )cycloalkenyl may be (C3-C 10 )cycloalkenyl, (C3-C5)cycloalkenyl, (C3-C4)cycloalkenyl, etc. In some specific embodiments, (C3-C 20 ) The cycloalkenyl group may be cyclopropenyl, cyclobutenyl, cyclopentenyl, etc.

[0064] In some embodiments, (C3-C 20 ) The heterocycloalkenyl group may be (C3-C 10 )heterocycloalkenyl, (C3-C5)heterocycloalkenyl, (C3-C4)heterocycloalkenyl, etc. In some specific embodiments, the heteroatom can be a halogen, a nitrogen atom, a sulfur atom, etc.

[0065] In some embodiments, (C2-C 20 ) alkynyl may be (C2-C 10 ) alkynyl, (C3-C 10 )alkynyl, (C3-C5)alkynyl, (C3-C4)alkynyl, (C2-C3)alkynyl, etc. In some specific embodiments, (C2-C 20 ) Alkynyl may be ethynyl, propynyl, butynyl, pentynyl, etc.

[0066] In some embodiments, (C2-C 20 ) heteroalkynyl can be (C2-C10 ) heteroalkynyl, (C3-C 10 ) heteroalkynyl, (C3-C5) heteroalkynyl, (C3-C4) heteroalkynyl, (C2-C3) heteroalkynyl, etc. In some specific embodiments, the heteroatom can be a halogen, a nitrogen atom, a sulfur atom, etc.

[0067] In some embodiments, (C3-C 20 ) The cycloalkynyl group may be (C3-C 10 )cycloalkynyl, (C3-C5)cycloalkynyl, (C3-C4)cycloalkynyl, etc. In some specific embodiments, (C2-C 20 ) The cycloalkynyl group may be cyclopropynyl, cyclobutynyl, cyclopentynyl, etc.

[0068] In some embodiments, (C3-C 20 ) The heterocycloalkynyl group may be (C3-C 10 ) heterocycloalkynyl, (C3-C5) heterocycloalkynyl, (C3-C4) heterocycloalkynyl, etc. In some specific embodiments, the heteroatom can be a halogen, a nitrogen atom, a sulfur atom, etc.

[0069] In some embodiments, (C1-C 20 ) The alkoxy group may be (C1-C 10 )alkoxy, (C1-C8)alkoxy, (C1-C6)alkoxy, (C1-C4)alkoxy, (C1-C3)alkoxy, (C1-C2)alkoxy. In some specific embodiments, (C1-C 20 ) Alkoxy may be, but is not limited to, methyloxy, ethyloxy, propyloxy, and the like.

[0070] In some embodiments, the aryl group can be, but is not limited to, a monocyclic aryl group, a polycyclic aryl group, or a condensed ring aryl group. In one embodiment, the aryl group is a monocyclic aryl group. In some specific embodiments, the aryl group is a phenyl group.

[0071] In some embodiments, the substituted aryl group may be, but is not limited to, a single or multiple substituted phenyl group at the ortho, meta, or para positions. The substituents include, but are not limited to, alkyl, substituted alkyl, halogen, alkoxyamino, nitro, -NR5R6, -NR5-CO-NR6, -OCONR5, -PR5R6, -SOR5, -SO2-R5, -SiR5R6R7, -BR5R6, wherein R5, R6, and R7 may be the same or different as described above. 1 , R 2The groups shown. Wherein, when the substituent is an alkyl group, the alkyl group may be, but not limited to, methyl, ethyl, propyl, butyl, isobutyl; when the substituent is a substituted alkyl group, the substituted alkyl group may be, but not limited to, trifluoromethyl, trichloromethyl, trifluoroethyl, trichloroethyl; when the substituent is a halogen, the halogen may be, but not limited to, fluorine, chlorine, bromine, iodine; when the substituent is an alkoxy group, the alkoxy group may be, but not limited to, methyloxy, ethyloxy, propyloxy. In one embodiment, the substituted aryl group may also be a cyano group (C1-C 10 )alkyl(C3-C8)aryl, substituted(C3-C8)aryl.

[0072] In some embodiments, the heteroaryl group can be (C3-C8)heteroaryl, furan, thiophene.

[0073] In some embodiments, the substituted heteroaryl can be a substituted (C3-C8) heteroaryl, an alkoxy substituted furan, a (C3-C8) heteroaryl substituted furan, an aliphatic chain substituted thiophene.

[0074] In some embodiments, the aryloxy group may be phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy.

[0075] In some embodiments, the aryl (C1-C 20 ) The alkyl group may be an aryl group (C1-C 10 ) alkyl, phenyl (C1-C 10 )alkyl, phenyl (C1-C5)alkyl, phenyl (C1-C4)alkyl, phenyl (C1-C3)alkyl, phenyl (C1-C2)alkyl, etc. In some specific embodiments, aryl (C1-C 20 ) The alkyl group may be phenylmethyl, phenylethyl, phenylpropyl, phenylbutyl, phenylisobutyl, phenylpentyl, phenylisopentyl, phenylneopentyl.

[0076] In some embodiments, the heteroaryl (C1-C 20 ) alkyl may be a heteroaryl (C1-C 10 ) alkyl, heteroaryl (C1-C 10 )alkyl, heteroaryl (C1-C5)alkyl, heteroaryl (C1-C4)alkyl, heteroaryl (C1-C3)alkyl, heteroaryl (C1-C2)alkyl, etc. In some specific embodiments, the heteroaryl group can be (C3-C8)heteroaryl, furan, pyridine, etc.

[0077] In some embodiments, (C2-C 20 )alkenyl (C1-C 20 ) The alkyl group may be (C2-C 10 )alkenyl (C1-C 10In some embodiments, the (C2-C5) alkenyl (C1-C3). 20 )alkenyl (C1-C 20 ) The alkyl group may be 2-butenyl, 2-pentenyl, 3-hexenyl, 3-heptenyl, or the like.

[0078] In some embodiments, (C2-C 20 ) alkynyl (C1-C 20 ) The alkyl group may be (C2-C 10 ) alkynyl (C1-C 10 )alkyl, (C2-C5)alkynyl, (C1-C3)alkyl. 20 ) alkynyl (C1-C 20 ) The alkyl group may be 2-butynyl, 2-pentynyl, 3-hexynyl, 3-heptynyl, or the like.

[0079] In some embodiments, the cyano group (C1-C 20 ) The alkyl group may be a cyano group (C1-C 10 )alkyl, cyano (C1-C5)alkyl, cyano (C1-C4)alkyl, cyano (C1-C3)alkyl, cyano (C1-C2)alkyl, etc. In some specific embodiments, cyano (C1-C 20 ) The alkyl group may be cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl or the like.

[0080] In some embodiments, the alkyloxycarbonylalkyl group can be (C1-C 10 )alkyloxycarbonyl (C1-C 10 )alkyl, (C1-C5)alkyloxycarbonyl(C1-C5)alkyl, (C1-C4)alkyloxycarbonyl(C1-C4)alkyl, (C1-C3)alkyloxycarbonyl(C1-C3)alkyl, (C1-C2)alkyloxycarbonyl(C1-C2)alkyl, etc. In some specific embodiments, the alkyloxycarbonylalkyl group can be ethoxycarbonylethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, methoxycarbonylmethyl, propoxycarbonylpropyl, propoxycarbonylethyl, propoxycarbonylmethyl, etc.

[0081] In some specific embodiments, the capture reagent B includes at least one of para-ester-substituted benzallyl malononitrile, ortho-ester-substituted benzallyl malononitrile, cis-1,2-bis(phenylsulfonyl)ethylene, (propylene-2-ene-1,2-disulfonyl)diphenyl, (E)-N-((4-acetylbenzyl)oxy)-1-(phenylsulfonyl)formimide cyanide, (E)-N-isobutoxy-1-(phenylsulfonyl)formimide cyanide, (E)-1-(phenylsulfonyl)-N-propoxyformimide cyanide, and p-toluenesulfonyl cyanide.

[0082] In some specific embodiments, the secondary alkylethylbenzene A includes at least one of (1-cyclohexylethyl)benzene, 4-(1-phenylethyl)tetrahydro-2H-pyran, (1-phenylethyl)cycloheptane, and (1s, 4r)-4-pentyl-4'-(1-phenylethyl)-1,1'-bis(cyclohexane).

[0083] In some specific embodiments, the addition product of the alkyl radical and the capture agent includes:

[0084]

[0085] At least one of .

[0086] In some embodiments, the acridinium salt photocatalyst has the general structural formula: Formula II; wherein X is a tetrafluoroborate anion, a hexafluorophosphate anion or a perchlorate anion, Ar is an aryl group or a substituted aryl group, R 7 , R 8 Each of the above groups is independently selected from the same or different alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, heteroalkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, heteroalkynyl, cycloalkynyl, heterocycloalkynyl, alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl, alkenylalkyl, alkynylalkyl and cyanoalkyl groups; these acridinium salt photocatalysts have a high oxidation potential and can oxidize the neutral benzene ring to promote the reaction.

[0087] In some embodiments, the acridinium salt photocatalyst R 7 , R 8 are independently selected from the same or different C1-C 20 Alkyl, C1-C 20 Heteroalkyl, C3-C 20 Cycloalkyl, C3-C 20 Heterocycloalkyl, C2-C 20 Alkenyl, C2-C 20 Heteroalkenyl, C3-C 20 Cycloalkenyl, C3-C 20 Heterocycloalkenyl, C2-C 20 Alkynyl, C2-C 20 Heteroalkynyl, C3-C 20 Cycloalkynyl, C3-C 20 Heterocycloalkynyl, C1-C 20 Alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, aryl (C1-C 20 ) alkyl, heteroaryl (C1-C 20 )alkyl, (C2-C 20)alkenyl (C1-C 20 )alkyl, (C2-C 20 ) alkynyl (C1-C 20 ) alkyl, cyano (C1-C 20 ) any one of the alkyl groups.

[0088] In some embodiments, the additive includes at least one of an oxidant, a Bronsted acid, and water. Further, in some embodiments, the additive includes an oxidant, a Bronsted acid, and water. Through the synergistic effect of acridine salt photocatalysts, oxidants, Bronsted acids, and water, the catalytic system has low toxicity, improved atom utilization and reaction efficiency, and few by-products. At the same time, the reaction process is made safe and controllable, simplifying the operation during the preparation and production process. Among them, the photocatalyst can provide better single-electron oxidation, thereby improving the efficiency of carbon-carbon bond breaking during the catalytic reaction. Oxidants and water are used for addition reactions of free radicals with heterocycles.

[0089] In the present application, the content of the photocatalyst, oxidant and water in the embodiment of the present invention is within a certain range of proportions, so that the reaction can have a high catalytic efficiency and obtain a target product with a high yield. In order to make the catalytic system play a more effective catalytic effect, in some embodiments, the molar ratio of acridinium salt photocatalyst, oxidant and water is (0.1-20): (0.1-20): (0.2-40); in this case, under the synergistic effect of photocatalyst, oxidant and water, the reaction has a high catalytic efficiency, which is conducive to improving the yield of the reaction product. In some preferred embodiments, the molar ratio of photocatalyst, oxidant and water is (0.2-20): 2.5: (1-10), in which case, it is conducive to obtaining the target product with the highest yield.

[0090] In some embodiments, the oxidant includes at least one of persulfate, high-valent iodine, quinone, potassium permanganate, peroxide, oxygen, and N-fluorobenzenesulfonimide, which are beneficial to promote the addition reaction of free radicals with heterocycles.

[0091] In some embodiments, the Bronsted acid includes at least one of acetic acid, fluoroacetic acid, sulfuric acid, hydrochloric acid, perchloric acid, phosphoric acid, and nitric acid; these Bronsted acids are beneficial to promote the addition reaction of free radicals with heterocycles.

[0092] In some embodiments, the organic solvent includes at least one of acetonitrile, nitromethane, dichloromethane, and 1,2-dichloromethane. The solvent is the result of a comprehensive screening, including solubility, boiling point reaction performance, and the organic solvent is preferably acetonitrile, which has good solubility for secondary alkylethylbenzene A, capture agent B, acridinium salt photocatalyst and additives.

[0093] The second aspect of the embodiment of the present application provides an addition product of an alkyl free radical and a capture agent obtained by the above method. The structural formula of the addition product of the alkyl free radical and the capture agent includes: At least one of; wherein R 1 , R 2 R is independently selected from the same or different alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, heteroalkenyl, alkoxy, fluorocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkynyl, heteroalkynyl, cycloalkynyl, heterocycloalkynyl, aryl, substituted aryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl, alkenylalkyl, alkynylalkyl, cyanoalkyl, alkyloxycarbonylalkyl, silylalkyl, halogen, trifluoromethoxy, sulfonamide, heterocyclic aryl, and hydrogen atom; 6 Any one selected from an ester group, an alkyl group, a heteroalkyl group, a hydrogen atom, a benzenesulfonyl group, an aryl group, an alkyl-substituted aryl group, and an alkoxy group.

[0094] The addition product of the alkyl free radical and the capture agent provided in the second aspect of the embodiment of the present application has high functionality and can be widely used in the fields of organic synthetic chemistry, biochemistry, asymmetric catalysis, pesticide and pharmaceutical research, such as in the synthesis of drug intermediates, the preparation of functional materials, and the preparation of chiral ligands such as metal ligands.

[0095] In some specific embodiments, the addition product of the alkyl radical and the capture agent includes:

[0096] At least one of .

[0097] In a third aspect of the embodiments of the present application, the addition product prepared by the above-mentioned addition method or the addition product of the above-mentioned alkyl free radical and the capture agent is at least applied to the synthesis of drug intermediates, the preparation of functional materials or the preparation of chiral ligands.

[0098] The addition product of the above-mentioned alkyl free radical and the capture agent provided in the third aspect of the embodiment of the present application can provide raw materials or reaction intermediates for the synthesis of drug intermediates, the preparation of functional materials or the preparation of chiral ligands due to its high functionality; it can provide diversified choices for the synthesis of drug intermediates, functional materials and applications.

[0099] In order to enable the above implementation details and operations of the present application to be clearly understood by those skilled in the art, as well as to demonstrate the significant improvement in the performance of the addition product of the alkyl free radical and the capture agent and the addition method thereof in the embodiments of the present application, the above technical scheme is illustrated by means of multiple embodiments below.

[0100] Example 1

[0101] A 2-(2-methyl-1-phenylpropyl)malononitrile compound, the structural formula of the 2-(2-methyl-1-phenylpropyl)malononitrile compound is shown in the following molecular structural formula 1:

[0102]

[0103] Its preparation comprises the steps of:

[0104] The photocatalyst Mes-Acr-PhBF4 (0.01mmol, 4.6mg), the trapping reagent benzylidenemalononitrile (0.2mmol, 30.8mg) and the oxidant ammonium persulfate (0.5mmol, 114mg) were weighed into an oven-dried 8mL vial equipped with a magnetic star bar. Acetonitrile and water (1mL and 0.1mL) were added, followed by secondary alkylethylbenzene ((1,2-dimethylpropyl)benzene, 0.4mmol). The reaction vessel was degassed, backfilled with argon, and then placed under a Kessil lamp at 450nm (40W). The progress of the reaction was monitored by TLC. After completion, the reaction mixture was concentrated and purified by silica gel flash column chromatography to obtain the target product with a yield of 81%.

[0105] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ7.49–7.37(m, 3H), 7.37–7.30(m, 2H), 4.19(d, J=5.7Hz, 1H), 2.87( dd, J=9.7, 5.7Hz, 1H), 2.42 (dp, J=9.7, 6.6Hz, 1H), 1.17 (d, J=6.6Hz, 3H), 0.86 (d, J=6.6Hz, 3H). 13 C NMR (101MHz, Chloroform-d) δ136.58, 129.12, 128.79, 128.25, 112.10, 111.82, 53.45, 30.24, 27.78, 20.94, 20.34.HRMS (ESI-TOF) calculated for C 13 H 14 N2(MH + ):197.1084, found:197.1079. This result further confirmed that the molecular structure of the product is exactly the same as the above-mentioned molecular structure 1.

[0106] Example 2

[0107] A 2-(1-phenyl-2-propylpentyl)malononitrile compound, the structural formula of the 2-(1-phenyl-2-propylpentyl)malononitrile compound is shown in the following molecular structural formula 2:

[0108]

[0109] The preparation method thereof refers to the preparation method of the compound in Example 1, except that the substrate is (3-propylhexyl-2-yl)benzene and the trapping reagent is benzylidenemalononitrile. The yield of the target product is 85%.

[0110] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ7.50–7.37 (m, 3H), 7.34 (dd, J=7.7, 1.9Hz, 2H), 4.18 (d, J=6.2Hz, 1H), 3.14 (dd, J=9 .4, 6.2Hz, 1H), 2.27–2.13 (m, 1H), 1.53–1.35 (m, 4H), 1.35–1.05 (m, 4H), 1.05–0.95 (m, 3H), 0.81 (t, J=6.9Hz, 3H). 13 CNMR (101MHz, Chloroform-d) δ136.47, 129.09, 128.72, 128.38, 112.23, 111.98, 49.3 4, 38.65, 32.21, 31.72, 27.68, 18.95, 18.77, 14.30, 14.19.HRMS (ESI-TOF) calculated forC 17 H 22 N2(MH + ):253.1710, found:253.1709. This result further confirmed that the molecular structure of the product is exactly the same as the above-mentioned molecular structure 2.

[0111] Example 3

[0112] A 2-(cyclobutyl(phenyl)methyl)malononitrile compound, the structural formula of the 2-(cyclobutyl(phenyl)methyl)malononitrile compound is shown in the following molecular structural formula 3:

[0113]

[0114] The preparation method thereof refers to the preparation method of the compound in Example 1, except that the substrate is (1-cyclobutylethyl)benzene and the trapping reagent is benzylidenemalononitrile. The yield of the target product is 72%.

[0115] The results of the relevant characterization analysis are 1H NMR (400MHz, Chloroform-d) δ7.47–7.36 (m, 3H), 7.36–7.30 (m, 2H), 3.92 (d, J=5.1Hz, 1H), 3.20 (dd, J=11.2 , 5.1Hz, 1H), 3.14–2.96 (m, 1H), 2.44–2.27 (m, 1H), 2.08–1.79 (m, 4H), 1.64 (ddt, J=13.1, 10.4, 2.7Hz, 1H). 13 C NMR (101MHz, Chloroform-d) δ135.51, 129.12, 128.83, 128.10, 111.98, 111.65, 52.72, 37.27, 27.89, 27.67, 27.04, 17.51.HRMS (ESI-TOF) calculated for C 14 H 14 N2(MH + ):209.1084, found:209.1080. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 3.

[0116] Example 4

[0117] A 2-(phenyl(spiro[3.3]hept-2-yl)methyl)malononitrile compound, the structural formula of the 2-(phenyl(spiro[3.3]hept-2-yl)methyl)malononitrile compound is shown in the following molecular structural formula 4:

[0118]

[0119] The preparation method thereof refers to the preparation method of the compound in Example 1, except that the substrate is 2-(1-phenylethyl)spiro[3.3]heptane and the trapping reagent is benzylidenemalononitrile. The yield of the target product is 79%.

[0120] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ7.49–7.36 (m, 3H), 7.35–7.30 (m, 2H), 3.91 (d, J=5.1Hz, 1H), 3.13 (dd, J=11.2, 5.1Hz, 1H), 2.85 (dddd, J =16.5, 11.3, 8.8, 7.6Hz, 1H), 2.44 (ddd, J=11.6, 7.5, 4.7Hz, 1H), 2.16–1.95 (m, 3H), 1.95–1.76 (m, 5H), 1.57 (dd, J=11.5, 9.0Hz, 1H). 13C NMR (101MHz, Chloroform-d) δ135.70, 129.11, 128.81, 128.08, 112.01, 111.71, 52.85 ,40.43,39.70,39.22,35.26,34.43,31.95,27.88,16.45.HRMS(ESI-TOF)calculated for C 17 H 18 N2(MH + ):249.1397, found:249.1396. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 4.

[0121] Example 5

[0122] A 2-(cyclopentyl(phenyl)methyl)malononitrile compound, the structural formula of the 2-(cyclopentyl(phenyl)methyl)malononitrile compound is shown in the following molecular structural formula 5:

[0123]

[0124] The preparation method thereof refers to the preparation method of the compound in Example 1, except that the substrate is (1-cyclopentylethyl)benzene and the trapping reagent is benzylidenemalononitrile. The yield of the target product is 84%.

[0125] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ7.42 (qd, J=7.5, 7.0, 4.6Hz, 5H), 4.11 (d, J=4.5Hz, 1H), 2.95 (dd, J=11.0, 4.5Hz, 1H), 2.58 (qt, J=10.0, 6.7 Hz, 1H), 2.08 (dtd, J=11.0, 7.2, 3.5Hz, 1H), 1.89–1.67 (m, 2H), 1.62 (tdd, J=11.7, 5.8, 3.4Hz, 3H), 1.38–1.29 (m, 1H), 1.15–0.98 (m, 1H). 13 C NMR (101MHz, Chloroform-d) δ137.32, 129.07, 128.76, 128.18, 112.05, 111.80, 52.29, 42.39, 31.68, 31.63, 29.17, 25.47, 24.76.HRMS (ESI-TOF) calculated for C 15 H 16 N2(MH +):223.1241, found:223.1239. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 5.

[0126] Example 6

[0127] A 2-(cyclohexyl(phenyl)methyl)malononitrile compound, the structural formula of the 2-(cyclohexyl(phenyl)methyl)malononitrile compound is shown in the following molecular structural formula 6:

[0128]

[0129] The preparation method thereof refers to the preparation method of the compound in Example 1, except that the substrate is (1-cyclohexylethyl)benzene and the trapping reagent is benzylidenemalononitrile. The yield of the target product is 88%.

[0130] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ7.47–7.37 (m, 3H), 7.37–7.31 (m, 2H), 4.22 (d, J=5.5Hz, 1H), 2.91 (dd, J=9.8, 5.4Hz, 1H), 2.11–1.99 (m, 1H), 1 ... 13 C NMR (101MHz, Chloroform-d) δ136.70, 129.12, 128.72, 128.29, 112.21, 111.94, 52.34, 39.23, 31.19, 30.58, 27.12, 25.84, 25.82, 25.73.HRMS (ESI-TOF) calculated for C 16 H 18 N2(MH + ):237.1397, found:237.1396. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 6.

[0131] Example 7

[0132] A 2-((4,4-difluorocyclohexyl)(phenyl)methyl)malononitrile compound, the structural formula of the 2-((4,4-difluorocyclohexyl)(phenyl)methyl)malononitrile compound is shown in the following molecular structural formula 7:

[0133]

[0134] The preparation method thereof refers to the preparation method of the compound in Example 1, except that the substrate is (1-(4,4-difluorocyclohexyl)ethyl)benzene and the trapping reagent is benzylidenemalononitrile. The yield of the target product is 78%.

[0135] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ7.50–7.39 (m, 3H), 7.35 (dd, J=7.6, 1.9Hz, 2H), 4.19 (d, J=5.2Hz, 1H), 2.98 (dd, J=9.9, 5.3Hz, 1H), 2.24 (dddd, J=17.0, 13.6 , 6.8, 4.3Hz, 1H), 2.18–1.99 (m, 3H), 1.89 (dtt, J=33.4, 13.5, 4.0Hz, 1H), 1.6 9(dddd, J=33.4, 17.6, 8.8, 4.0Hz, 1H), 1.60–1.44(m, 2H), 1.32–1.20(m, 1H). 13 C NMR (101MHz, Chloroform-d) δ 136.17, 129.46, 129.19, 127.97, 111.67, 51.19, 37.66, 33.01 (t, J=25.9Hz), 27.52, 27.27, 27.17, 26.86, 26.76. 19 F NMR (376MHz, Chloroform-d) δ -93.09 (d, J = 237.2Hz), -103.02 (d, J = 237.4Hz). HRMS (ESI-TOF) calculated for C 16 H 16 F2N2(MH + ):273.1209, found:273.1210. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 7.

[0136] Example 8

[0137] A 2-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)malononitrile compound, the structural formula of the 2-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)malononitrile compound is shown in the following molecular structural formula 8:

[0138]

[0139] The preparation method thereof is similar to that of Example 1, except that the substrate is 4-(1-phenylethyl)tetrahydro-2H-pyran and the trapping reagent is benzylidenemalononitrile. The yield of the target product is 70%.

[0140] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ7.50–7.39 (m, 3H), 7.39–7.33 (m, 2H), 4.19 (d, J=5.0Hz, 1H), 4.15 –4.05 (m, 1H), 3.92 (ddd, J=11.8, 5.0, 1.7Hz, 1H), 3.51 (td, J=11.9, 2.3Hz, 1H), 3.36 (td, J=11. 8, 2.4Hz, 1H), 2.93 (dd, J=10.2, 5.0Hz, 1H), 2.38–2.22 (m, 1H), 1.84 (ddd, J=12.6, 4.0, 2.1Hz, 1 H), 1.50 (qd, J=12.1, 4.6Hz, 1H), 1.32 (dddd, J=17.6, 15.4, 3.7, 1.9Hz, 1H), 1.27–1.17 (m, 1H). 13 C NMR (101MHz, Chloroform-d) δ135.73, 129.35, 129.10, 128.22, 111.80, 111.66, 67.54, 67.12, 51.95, 36.97, 31.05, 30.67, 26.82.HRMS (ESI-TOF) calculated for C 15 H 16 N2O(MH + ):239.1190, found:239.1189. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 8.

[0141] Example 9

[0142] A 2-(cycloheptyl(phenyl)methyl)malononitrile compound, the structural formula of the 2-(cycloheptyl(phenyl)methyl)malononitrile compound is shown in the following molecular structural formula 9:

[0143]

[0144] The preparation method thereof refers to the preparation method of the compound in Example 1, except that the substrate is (1-cycloheptylethyl)benzene and the trapping reagent is benzylidenemalononitrile. The yield of the target product is 96%.

[0145] The results of the relevant characterization analysis are 1H NMR (400MHz, Chloroform-d) δ7.48–7.38 (m, 3H), 7.38–7.30 (m, 2H), 4.22 (d, J=5.8Hz, 1H), 3.03 (dd, J=9.7, 5.8Hz, 1 H), 2.39–2.18 (m, 1H), 1.96 (ddt, J=15.9, 8.0, 4.0Hz, 1H), 1.80–1.45 (m, 8H), 1.43–1.28 (m, 2H), 1.26–1.13 (m, 1H). 13 C NMR (101MHz, Chloroform-d) δ136.91, 129.10, 128.71, 128.43, 112.25, 111.94, 52.13, 40.43, 32.62, 30.64, 28.58, 27.81, 27.74, 25.92, 25.85.HRMS(ESI-TOF)calculatedfor C 17 H 20 N2(MH + ):251.1554, found:251.1553. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 9.

[0146] Example 10

[0147] A (1S, 2R, 4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-yl-4-(1,1-dicyano-3-propylhexyl-2-yl)benzoate compound, the structural formula of the (1S, 2R, 4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-yl-4-(1,1-dicyano-3-propylhexyl-2-yl)benzoate compound is shown in the following molecular structural formula 10:

[0148]

[0149] The preparation method thereof is similar to that of Example 1, except that the capture agent is para-ester-substituted benzyl malononitrile, and the secondary alkyl ethylbenzene A is (3-propylhex-2-yl)benzene. The yield of the target product is 89%, and the dr is 1:1.

[0150] The results of the relevant characterization analysis are 1H NMR (500MHz, Chloroform-d) δ8.11 (d, J=8.3Hz, 2H), 7.43 (d, J=8.4Hz, 2H), 5.20–5.02 (m, 1H), 4.2 0 (d, J=6.2Hz, 1H), 3.19 (dd, J=9.5, 6.1Hz, 1H), 2.59–2.43 (m, 1H), 2.25–2.17 (m, 1H), 2.14 (ddd, J= 10.8, 9.4, 4.4Hz, 1H), 1.82 (ddt, J=12.1, 8.1, 3.9Hz, 1H), 1.76 (t, J=4.5Hz, 1H), 1.43 (tt, J=8.5, 5.1Hz, 4H), 1.37–1.03 (m, 7H), 0.99 (d, J=6.8Hz, 6H), 0.93 (d, J=1.3Hz, 6H), 0.79 (t, J=7.0Hz, 3H). 13 C NMR (126MHz, Chloroform-d) δ166.19, 141.31, 131.41, 130.30, 128.54, 112.00, 111.70, 80.90, 49.27, 49.15, 47.95, 4 5.03, 38.66, 36.93, 32.13, 31.78, 28.12, 27.43, 19.76, 18.95, 18.76, 14.30, 14.19, 13.66.HRMS (ESI-TOF) calculated for C 28 H 38 N2O2(MH + ):433.2861, found:433.2861. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 10.

[0151] Embodiment 11

[0152] A (1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl 4-(2,2-dicyano-1-cyclohexylethyl) benzoate, the structural formula of the (1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl 4-(2,2-dicyano-1-cyclohexylethyl) benzoate compound is shown in the following molecular structural formula 11:

[0153]

[0154] The preparation method thereof is similar to that of Example 1, except that the capture agent is benzallyl malononitrile substituted with an ortho-ester group, and the secondary alkyl ethylbenzene A is (1-cyclohexylethyl)benzene. The yield of the target product is 89%, and the dr is 1:1.

[0155] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ8.07 (dt, J=7.1, 1.7Hz, 1H), 8.00 (dt, J=7.4, 1.8Hz, 1H), 7.64–7.43 (m , 2H), 4.97 (tdd, J=10.9, 4.4, 2.2Hz, 1H), 4.25 (dd, J=5.8, 2.0Hz, 1H), 3.02 (ddd, J=9.3, 5.8, 3.2Hz, 1 H), 2.22–2.13 (m, 1H), 2.13–1.92 (m, 3H), 1.92–1.81 (m, 1H), 1.81–1.65 (m, 4H), 1.60 (ddq, J=12.1, 8 .8, 3.1Hz, 2H), 1.53–1.35 (m, 2H), 1.26–1.04 (m, 5H), 0.99–0.85 (m, 8H), 0.83 (dd, J=7.0, 1.2Hz, 3H). 13 C NMR (101MHz, Chloroform-d) δ165.43, 137.13, 136.98, 132.24, 132.15, 131.72, 131.66, 129.85, 129.83, 129.56, 129.24, 129.21, 112.01, 111.99, 111.76, 111.74, 75.28, 52.11, 52.07, 47.23, 47 .19, 40.92, 39.32, 39.28, 34.30, 31.46, 31.17, 30.41, 30.38, 26.94, 26.85, 26.65, 26.50, 25.78, 25.75, 25.69, 25.64, 23.80, 23.67, 22.04, 20.76, 20.71, 16.7, 16.58.HRMS (ESI-TOF) calculated for C 27 H 36 N2O2(MH + ):419.2704, found:419.2707. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 11.

[0156] Example 12

[0157] A 2-cyclohexyl-4-methylquinoline compound, the structural formula of the 2-cyclohexyl-4-methylquinoline compound is shown in the following molecular structural formula 12:

[0158]

[0159] Its preparation comprises the steps of:

[0160] Photocatalyst Mes-Acr-PhBF4 (0.01mmol, 4.6mg), ammonium persulfate (0.5mmol) and heterocycle (0.2mmol) were weighed into an oven-dried 8mL vial equipped with a magnetic star bar. H2O (0.1mL) and MeCN (0.9mL) were added, followed by secondary alkyl ethylbenzene (0.4mmol) and then trifluoroacetic acid (0.4mmol). The reaction vessel was degassed and backfilled with argon, then placed under a Kessil lamp at 450nm for irradiation (40W). The reaction progress was monitored by TLC. After completion, the reaction mixture was quenched with 1N NaOH (10mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by silica gel flash column. The yield of compound 12 was 61%.

[0161] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ8.09 (d, J=8.4Hz, 1H), 7.97 (dd, J=8.4, 1.4Hz, 1H), 7.69 (ddd, J=8.4, 6.8, 1.4Hz, 1H), 7.52 (ddd, J=8.2, 6.9, 1.3Hz, 1H), 7.20 (d, J=1.1Hz, 1H), 2.92 (tt, J=12.0, 3.4Hz, 1 H), 2.71 (d, J=1.0Hz, 3H), 2.10–2.00 (m, 2H), 1.92 (dt, J=12.8, 3.3Hz, 2H), 1.82 (dqd, J=12.7, 2.9, 1 .4Hz, 1H), 1.65 (qd, J=12.5, 3.1Hz, 2H), 1.50 (qt, J=12.6, 3.3Hz, 2H), 1.36 (qt, J=12.8, 3.4Hz, 1H). 13 CNMR (101MHz, Chloroform-d) δ166.47, 129.37, 129.01, 127.03, 125.42, 123.56, 120.24, 47.53, 32.83, 26.56, 26.13, 18.87.HRMS (ESI-TOF) calculated for C 16 H 19 N(M+H + ):226.1590, found:226.1592. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 12.

[0162] Embodiment 13

[0163] A (2-cyclohexylethane-1,1-diyldisulfonyl)diphenyl compound, the structural formula of the (2-cyclohexylethane-1,1-diyldisulfonyl)diphenyl compound is shown in the following molecular structural formula 13:

[0164]

[0165] The preparation method thereof is similar to that of Example 1, except that the trapping agent is alkenyl sulfone, the trapping agent is 2.0 equivalents, and the secondary alkyl ethylbenzene A is (1-cyclohexylethyl)benzene. The yield of the target product is 61%.

[0166] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ 8.06–7.90 (m, 4H), 7.73 (t, J = 7.5Hz, 2H), 7.61 (t, J = 7.7Hz, 4H), 4.49 (t, J = 5.6Hz, 1H), 2.1 0–1.94 (m, 2H), 1.77–1.56 (m, 5H), 1.49 (ddd, J=10.8, 7.4, 3.5Hz, 1H), 1.16 (tt, J=20.4, 11.0Hz, 3H), 0.89–0.70 (m, 2H). 13 C NMR (101MHz, Chloroform-d) δ137.88, 134.56, 129.65, 129.10, 81.35, 35.66, 32.61, 32.53, 26.13, 25.76.HRMS (ESI-TOF) calculated for C 20 H 24 O4S2(MH + ):391.1043, found:391.1044. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 13.

[0167] Embodiment 14

[0168] A ((2-cyclohexylvinyl)sulfonyl)benzene compound, wherein the structural formula of the ((2-cyclohexylvinyl)sulfonyl)benzene is shown in the following molecular structural formula 14:

[0169]

[0170] The preparation method thereof refers to the preparation method of the compound in Example 1, except that the capture reagent is cis-1,2-bis(phenylsulfonyl)ethylene, the capture reagent is 2.0 equivalents, and the secondary alkyl ethylbenzene A is (1-cyclohexylethyl)benzene. The yield of the target product is 58%.

[0171] The results of the relevant characterization analysis are 1 H NMR (500MHz, Chloroform-d) δ7.98–7.80 (m, 4H), 7.61 (td, J=7.0, 1.7Hz, 2H), 7.57–7.50 (m, 4H), 6.96 (dd, J=15.2, 6.4Hz, 1H), 6.32–6.13 (m, 2H), 6.04 (t , J=10.9Hz, 1H), 3.31 (qt, J=11.2, 3.7Hz, 1H), 2.18 (dddtd, J=11.3, 9.8, 6.6 , 3.3, 1.4Hz, 1H), 1.80–1.59 (m, 10H), 1.37–1.23 (m, 4H), 1.21–0.98 (m, 6H). 13 C NMR (126MHz, Chloroform-d) δ151.95, 151.86, 140.85, 133.29, 133.21, 129.61, 129.25, 129.23, 128.60, 12 8.31, 127.55, 127.30, 39.93, 36.60, 31.92, 31.30, 25.76, 25.67, 25.58, 25.12.HRMS (ESI-TOF) calculated for C 14 H 18 O2S(M+H + ):251.1100, found:251.1100. This result further confirmed that the molecular structure of the product was exactly the above-mentioned molecular structure 14.

[0172] Embodiment 15

[0173] A ((3-cyclohexylprop-1-en-2-yl)sulfonyl)benzene compound, the structural formula of the ((3-cyclohexylprop-1-en-2-yl)sulfonyl)benzene compound is shown in the following molecular structural formula 15:

[0174]

[0175] The preparation method thereof refers to the preparation method of the compound in Example 1, except that: the capture reagent is (prop-2-ene-1,2-disulfonyl) diphenyl, the capture reagent is 2.0 equivalents, and the secondary alkyl ethylbenzene A is (1-cyclohexylethyl) benzene. The yield of the target product is 75%.

[0176] The results of the relevant characterization analysis are 1H NMR (400MHz, Chloroform-d) δ7.98–7.85 (m, 2H), 7.73–7.61 (m, 1H), 7.61–7.50 (m, 2H), 6.43 (s, 1H), 5.73 (s, 1H), 2.1 4(dd, J=7.2, 1.3Hz, 2H), 1.69–1.58 (m, 5H), 1.46 (ttt, J=10.8, 7.1, 3.2Hz, 1H), 1.21–1.06 (m, 3H), 0.84–0.71 (m, 2H). 13 C NMR (101MHz, Chloroform-d) δ148.81, 133.37, 129.68, 129.10, 128.30, 124.39, 37.31, 35.75, 32.77, 26.27, 25.97.HRMS (ESI-TOF) calculated for C 15 H 20 O2S(M+H + ):265.1257, found:265.1257. This result further confirmed that the molecular structure of the product was exactly the above-mentioned molecular structure 15.

[0177] Example 16

[0178] A (Z)-N-((4-acetylbenzyl)oxy)cyclohexane iminocyanate compound, the structural formula of the (Z)-N-((4-acetylbenzyl)oxy)cyclohexane iminocyanate compound is shown in the following molecular structural formula 16:

[0179]

[0180] The preparation method thereof is similar to that of Example 1, except that: the capture reagent is (E)-N-((4-acetylbenzyl)oxy)-1-(phenylsulfonyl)carboximide cyanide, the capture reagent is 2.0 equivalents, and the secondary alkylethylbenzene A is (1-cyclohexylethyl)benzene. The yield of the target product is 46%.

[0181] The results of the relevant characterization analysis are 1H NMR (400MHz, Chloroform-d) δ8.05–7.93 (m, 2H), 7.47 (d, J=8.3Hz, 2H), 5.30 (s, 2H), 2.64 (s, 3H), 2.45 (tt, J=11.6, 3.5Hz, 1H), 1.86 (ddt, J=24.8, 12.4, 2.7Hz, 4H), 1.75–1.68 (m, 1H), 1.49–1.36 (m, 2H), 1.27 (dddd, J=26.3, 15.5, 9.2, 3.1Hz, 3H). 13 C NMR (101MHz, Chloroform-d) δ197.70, 141.50, 137.95, 136.91, 128.57, 128.08, 109.70, 40.84, 29.89, 28.73, 26.67, 25.35, 25.31.HRMS (ESI-TOF) calculated for C 17 H 20 N2O2(M+H + ):285.1598, found:285.1597. This result further confirmed that the molecular structure of the product was exactly the same as the above-mentioned molecular structure 16.

[0182] Embodiment 17

[0183] A (Z)-N-isopropoxytetrahydro-2H-pyran-4-formyl cyanide compound, the structural formula of the (Z)-N-isopropoxytetrahydro-2H-pyran-4-formyl cyanide compound is shown in the following molecular structural formula 17:

[0184]

[0185] The preparation method thereof is similar to that of Example 1, except that: the capture reagent is (E)-N-isobutyloxy-1-(phenylsulfonyl)carboximide cyanide, the capture reagent is 2.0 equivalents, and the secondary alkyl ethylbenzene A is 4-(1-phenylethyl)tetrahydro-2H-pyran. The yield of the target product is 76%.

[0186] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ4.59–4.43 (m, 1H), 4.11–3.98 (m, 2H), 2.80–2.62 (m, 1H), 2.00–1.67 (m, 4H), 1.32 (dd, J=6.3, 4.5Hz, 6H). 13CNMR (101MHz, Chloroform-d) δ133.90, 109.87, 66.97, 38.15, 29.63, 28.32, 21.33, 21.25.HRMS (ESI-TOF) calculated for C 10 H 16 N2O2(M+H + ):197.1285, found:197.1287. This result further confirmed that the molecular structure of the product was exactly the above-mentioned molecular structure 17.

[0187] Embodiment 18

[0188] A (Z)-N-ethoxycycloheptane iminocyanate compound, the structural formula of the (Z)-N-ethoxycycloheptane iminocyanate compound is shown in the following molecular structural formula 18:

[0189]

[0190] The preparation method thereof refers to the preparation method of the compound in Example 1, except that: the capture reagent is (E)-1-(phenylsulfonyl)-N-propoxycarbonimide cyanide, the capture reagent is 2.0 equivalents, and the secondary alkyl ethylbenzene A is (1-phenylethyl) cycloheptane. The yield of the target product is 75%.

[0191] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ4.27 (q, J=7.1Hz, 2H), 2.63 (tt, J=10.0, 4.1Hz, 1H) , 1.99–1.74(m, 4H), 1.70–1.60(m, 4H), 1.60–1.47(m, 4H), 1.34(t, J=7.1Hz, 3H). 13 C NMR (101MHz, Chloroform-d) δ137.06, 110.24, 71.49, 42.59, 31.88, 27.92, 26.06, 14.34.HRMS (ESI-TOF) calculated for C 11 H 18 N2O(M+H + ):195.1492, found:195.1494. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 18.

[0192] Embodiment 19

[0193] A (1's, 4'r)-4'-pentyl-[1,1'-bis(cyclohexane)]-4-nitrile compound, wherein the structural formula of the ((1's, 4'r)-4'-pentyl-[1,1'-bis(cyclohexane)]-4-nitrile is shown in the following molecular structural formula 19:

[0194]

[0195] The preparation method thereof refers to the preparation method of the compound in Example 1, except that: the capture reagent is p-toluenesulfonyl cyanide, the capture reagent is 2.0 equivalents, and the secondary alkyl ethylbenzene A is (1s, 4r)-4-pentyl-4'-(1-phenylethyl)-1,1'-bis(cyclohexane). The yield of the target product is 67%, and the dr is 1:1.

[0196] The results of the relevant characterization analysis are 1 H NMR (400MHz, Chloroform-d) δ2.92 (q, J=3.7Hz, 1H), 2.41–2.28 (m, 1H), 2.19– 2.08(m, 2H), 2.08–1.97(m, 2H), 1.86–1.66(m, 12H), 1.62–1.48(m, 4H), 1.43(d dd, J=13.6, 10.7, 2.9Hz, 2H), 1.29 (tdd, J=13.3, 8.5, 4.8Hz, 12H), 1.21–1.05( m, 10H), 0.99 (tdd, J=12.0, 8.3, 2.9Hz, 6H), 0.89 (qd, J=8.4, 7.6, 2.1Hz, 10H). 13 C NMR (101MHz, Chloroform-d) δ122.94, 122.27, 42.89, 42.82, 42.50, 41.90, 37.84, 37.80, 37.39, 37.37, 33.46, 33.4 3, 32.23, 32.21, 30.17, 29.96, 29.87, 28.68, 28.46, 27.34, 26.66, 25.99, 22.71, 14.11.HRMS (ESI-TOF) calculated for C 18 H 31 N(M+H + ):262.2529, found:262.2531. This result further confirmed that the molecular structure of the product is exactly the above-mentioned molecular structure 19.

[0197] The above description is only a preferred embodiment of the present application and is not intended to limit the present application. Any modifications, equivalent substitutions and improvements made within the spirit and principles of the present application should be included in the protection scope of the present application.

Claims

1. A method for adding an alkyl radical to a capture agent, characterized in that: The following steps are involved: Dissolving secondary alkylethylbenzene A, capture agent B, acridinium salt photocatalyst and additives in an organic solvent, and performing a light irradiation reaction to obtain an addition product of an alkyl free radical and the capture agent; Wherein, the general structural formula of the secondary alkyl ethylbenzene A is: The capture agent B is selected from At least one of; The structural formula of the addition product of the alkyl radical and the capture agent includes: At least one of; Among them, R 1 , R 2 R is independently selected from the same or different alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, heteroalkenyl, alkoxy, fluorocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkynyl, heteroalkynyl, cycloalkynyl, heterocycloalkynyl, aryl, substituted aryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl, alkenylalkyl, alkynylalkyl, cyanoalkyl, alkyloxycarbonylalkyl, silylalkyl, halogen, trifluoromethoxy, sulfonamide, heterocyclic aryl, and hydrogen atom; 4 , R 5 Each of them is independently selected from the same or different ester group, alkyl group, heteroalkyl group, hydrogen atom, benzenesulfonyl group, aryl group, alkyl-substituted aryl group and alkoxy group.

2. The method for adding an alkyl radical to a capture agent according to claim 1, wherein: The molar ratio of the acridinium salt photocatalyst, the additive, the secondary alkylethylbenzene A and the capture agent B is (0.1-20):(0.1-20):(0.2-40):(1-100); And / or, the conditions of the light irradiation reaction include: reacting in an inert atmosphere with an irradiation wavelength of 400nm to 480nm for 24 to 48h.

3. The method for adding an alkyl radical to a capture agent according to claim 2, wherein: The general structural formula of the acridinium salt photocatalyst is: Wherein, X is tetrafluoroborate anion, hexafluorophosphate anion or perchlorate anion, Ar is an aryl group or a substituted aryl group, R 7 , R 8 are independently selected from any one of the following groups: alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkenyl, heteroalkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, heteroalkynyl, cycloalkynyl, heterocycloalkynyl, alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl, alkenylalkyl, alkynylalkyl, cyanoalkyl; and / or, the additive comprises at least one of an oxidant, a Bronsted acid, and water; And / or, the organic solvent comprises at least one of acetonitrile, nitromethane, dichloromethane, and 1,2-dichloromethane; And / or, the capture agent B includes at least one of cis-1,2-bis(phenylsulfonyl)ethylene and (propylene-2-ene-1,2-disulfonyl)diphenyl.

4. The method for adding an alkyl radical to a capture agent according to claim 3, wherein: The additives include an oxidant, a Bronsted acid and water; And / or, the molar ratio of the acridinium salt photocatalyst, the oxidant and water is (0.1-20):(0.1-20):(0.2-40); and / or, the oxidant comprises at least one of persulfate, high-valent iodine, quinones, potassium permanganate, peroxides, oxygen, and N-fluorobenzenesulfonimide; And / or, the Bronsted acid comprises at least one of acetic acid, fluoroacetic acid, sulfuric acid, hydrochloric acid, perchloric acid, phosphoric acid, and nitric acid; and / or, the R 7 , the R 8 are independently selected from the same or different C1-C 20 Alkyl, C1-C 20 Heteroalkyl, C3-C 20 Cycloalkyl, C3-C 20 Heterocycloalkyl, C2-C 20 Alkenyl, C2-C 20 Heteroalkenyl, C3-C 20 Cycloalkenyl, C3-C 20 Heterocycloalkenyl, C2-C 20 Alkynyl, C2-C 20 Heteroalkynyl, C3-C 20 Cycloalkynyl, C3-C 20 Heterocycloalkynyl, C1-C 20 Alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, aryl (C1-C 20 ) alkyl, heteroaryl (C1-C 20 )alkyl, (C2-C 20 )alkenyl (C1-C 20 )alkyl, (C2-C 20 ) alkynyl (C1-C 20 ) alkyl, cyano (C1-C 20 ) alkyl.

5. The method for adding an alkyl radical to a capture agent according to any one of claims 1 to 4, characterized in that: The R 1 , the R 2 are independently selected from the same or different C1-C 20 Alkyl, C1-C 20 Heteroalkyl, C3-C 20 Cycloalkyl, C3-C 20 Heterocycloalkyl, C2-C 20 Alkenyl, C2-C 20 Heteroalkenyl, C3-C 20 Cycloalkenyl, C3-C 20 Heterocycloalkenyl, C2-C 20 Alkynyl, C2-C 20 Heteroalkynyl, C3-C 20 Cycloalkynyl, C3-C 20 Heterocycloalkynyl, C1-C 20 Alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, aryl (C1-C 20 ) alkyl, heteroaryl (C1-C 20 ) alkyl, C2-C 20 Alkenyl (C1-C 20 ) alkyl, C2-C 20 Alkynyl (C1-C 20 ) alkyl, cyano (C1-C 20 ) alkyl, alkyloxy, carbonylalkyl, silylalkyl C3-C 20 , halogen, trifluoromethoxy, sulfonamide, hydrogen atom; and / or, the R 4 , the R 5 are independently selected from the same or different ester groups, C1-C 20 Alkyl, C1-C 20 Heteroalkyl, hydrogen atom, benzenesulfonyl, aryl, C1-C 20 Alkyl substituted aryl, C1-C 20 Any of the alkoxy groups; And / or, the heterocyclic ring includes any one of quinoline, pyridine, thiazole, benzothiazole, pyrazine, pyrimidine and purine.

6. The method for adding an alkyl radical to a capture agent according to claim 5, wherein: The R 1 , the R 2 are independently selected from the same or different C1-C 10 Alkyl, C1-C 10 Heteroalkyl, C3-C 10 Cycloalkyl, C3-C 10 Heterocycloalkyl, C2-C 10 Alkenyl, C2-C 10 Heteroalkenyl, C3-C 10 Cycloalkenyl, C3-C 10 Heterocycloalkenyl, C2-C 10 Alkynyl, C2-C 10 Heteroalkynyl, C3-C 10 Cycloalkynyl, C3-C 10 Heterocycloalkynyl, C1-C 10 Alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, aryl (C1-C 10 ) alkyl, heteroaryl (C1-C 10 ) alkyl, C2-C 10 Alkenyl (C1-C 10 ) alkyl, C2-C 10 Alkynyl (C1-C 10 ) alkyl, cyano (C1-C 10 ) alkyl, alkyloxy, carbonylalkyl, silylalkyl C3-C 10 , halogen, trifluoromethoxy, sulfonamide, hydrogen atom; and / or, the R 4 , the R 5 are independently selected from the same or different ester groups, C1-C 10 Alkyl, C1-C 10 Heteroalkyl, hydrogen atom, benzenesulfonyl, aryl, C1-C 10 Alkyl substituted aryl, C1-C 10 Any of the alkoxy groups.

7. The method for adding an alkyl radical to a capture agent according to claim 6, wherein: The R 1 , the R 2 are independently selected from the same or different C1-C5 alkyl, C1-C5 heteroalkyl, C3-C5 cycloalkyl, C3-C5 heterocycloalkyl, C2-C5 alkenyl, C2-C5 heteroalkenyl, C3-C5 cycloalkenyl, C3-C5 heterocycloalkenyl, C2-C5 alkynyl, C2-C5 heteroalkynyl, C3-C5 cycloalkynyl, C3-C5 heterocycloalkynyl, C1-C5 alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, aryloxy, heteroaryloxy, aryl (C1-C 20 )alkyl, heteroaryl (C1-C5)alkyl, C2-C5 alkenyl (C1-C5)alkyl, C2-C5 alkynyl (C1-C5)alkyl, cyano (C1-C5)alkyl, alkyloxy, carbonylalkyl, silylalkyl C3-C5, halogen, trifluoromethoxy, sulfonamide, hydrogen atom; and / or, the R 4 , the R 5 Each of them is independently selected from the same or different ester groups, C1-C5 alkyl groups, C1-C5 heteroalkyl groups, hydrogen atoms, benzenesulfonyl groups, aryl groups, C1-C5 alkyl-substituted aryl groups, and C1-C5 alkoxy groups; And / or, the secondary alkylethylbenzene A includes (1-cyclohexylethyl)benzene.

8. An addition product of an alkyl radical and a capture agent obtained by the method according to any one of claims 1 to 7, characterized in that: The structural formula of the addition product of the alkyl radical and the capture agent includes: At least one of .

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