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

Abstract

The present application belongs to the technical field of organic synthesis, and particularly relates to an addition product of an alkyl radical and a capture agent, and its addition method and application. A secondary alkyl ethylbenzene A, a capture agent B, an acridinium salt photocatalyst, and an additive are dissolved in an organic solvent and subjected to a light-irradiation reaction to obtain an addition product of the alkyl radical and the capture agent; wherein the secondary alkyl ethylbenzene A has the general structural formula: #imgabs0# Formula I; the capture agent B is selected from at least one of #imgabs1##imgabs2#TsCN; and the structural formula of the addition product of the alkyl radical and the capture agent includes at least one of #imgabs3#. A method is proposed for inducing carbon-carbon bond cleavage in secondary alkyl ethylbenzene by single-electron transfer oxidation, which reacts with a capture agent to generate a product. The reactant raw materials are easily accessible, the reaction process is safe and controllable, the operation is simple, and the production cost is low. The addition product has high functionality and more diverse applications.

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 reagent, and an addition method and application thereof. Background Art

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

[0003] A large number of alkyl radical precursors have been developed that possess a built-in redox group that can narrow the energy gap between the substrate and the excited state of the photosensitizer. Despite these advances, generating alkyl radicals in a precisely controlled manner using common, environmentally friendly 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 present application aims to provide an addition product of an alkyl radical with a trapping agent, its addition method, and application, aiming to provide a new method for expanding alkyl radical chemistry using secondary alkylethylbenzenes.

[0005] To achieve the above application objectives, the technical solutions adopted in this application are 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 radical and the capture agent;

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

[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 the groups is independently selected from the same or different ester groups, alkyl groups, heteroalkyl groups, hydrogen atoms, benzenesulfonyl groups, aryl groups, alkyl-substituted aryl groups, and alkoxy groups.

[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 the group consisting of an ester group, an alkyl group, a heteroalkyl group, a hydrogen atom, a phenylsulfonyl 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-mentioned addition method or the addition product of the above-mentioned alkyl 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 reagents, which oxidizes secondary alkylethylbenzene A through single electron transfer, and subsequently induces carbon-carbon bond cleavage thereof through proton-coupled electron transfer (PCET), and then reacts with capture reagent B to generate an addition product of alkyl radicals and capture reagents. 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 alkylethylbenzenes is realized, and a previously unrealized method for carbon-carbon bond cleavage of secondary alkylethylbenzenes 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 reagents. This method represents a new method for expanding alkyl radical chemistry using secondary alkylethylbenzenes. The generated alkyl radicals can be captured by a variety of capture reagents, including electron-deficient double bonds, heterocycles, p-toluenesulfonyl cyanide, etc. In addition, the reactant raw materials are easily accessible, and no additional modification is required before the reaction, allowing direct use in production. The reaction process is safe and controllable, simplifying the operational steps and shortening the reaction route. This significantly reduces the production cost of preparing such captured addition products, greatly expanding the designability and application prospects of such compounds. Furthermore, the addition products obtained by this method possess high functionality, making them more diverse in applications such as the synthesis of pharmaceutical intermediates, functional materials, and metal ligands. They can be widely used in the synthesis of pharmaceutical intermediates, the preparation of chiral ligands, and functional materials, effectively reducing the economic cost of preparing pharmaceutical intermediates and functional materials, and improving their environmental friendliness.

[0015] The addition product of the alkyl free radical and the capture reagent provided in the second aspect of this application has high functionality and can be widely used in 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 reagent provided in the third aspect of this application, due to its high functionality, can provide raw materials or reaction intermediates for the synthesis of drug intermediates, the preparation of functional materials or the preparation of chiral ligands; it can provide diversified options 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 this 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 this application and are not intended to limit this application.

[0018] In this application, the term "and / or" describes the relationship between associated objects, indicating that three possible relationships exist. For example, A and / or B can represent: A exists alone, A and B exist simultaneously, 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 mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, c can be single or multiple.

[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. 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 otherwise.

[0022] The weights of the relevant components mentioned in the examples of this specification may not only refer to the specific content of each component, but also represent the weight ratio between the components. Therefore, as long as the content of the relevant components in the examples of this specification is proportionally enlarged or reduced according to the examples of this specification, it is within the scope disclosed in the examples of this specification. Specifically, the mass in the examples of this specification may be μg, mg, g, kg, etc., which are mass units known in the chemical industry.

[0023] The terms "first" and "second" are used solely for descriptive purposes to distinguish objects, such as substances, from one another and should not be understood to indicate or imply relative importance or to implicitly specify the quantity of the technical features being referred to. For example, without departing from the scope of the embodiments of this application, a first XX may also be referred to as a second XX, and similarly, a second XX may also be referred to as a first XX. Thus, features defined as "first" or "second" may explicitly or implicitly include one or more of such 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 a straight or branched chain hydrocarbon 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 chain hydrocarbon with 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 a straight or branched chain hydrocarbon having one or more triple bonds, including but not limited to ethynyl, propynyl, and 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 the like.

[0033] "Heteroaryl" refers to a monocyclic, polycyclic, or condensed-ring aromatic hydrocarbon in which one or more carbon atoms have been replaced by a heteroatom such as nitrogen, oxygen, or sulfur. If the heteroaryl group contains more than one heteroatom, the 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, pyrido[3,4-b]indolyl, pyridyl, pyrimidinyl, pyrrolyl, quinolizinyl, quinolyl, quinoxalinyl, thiadiazolyl, thiatriazolyl, thiazolyl, thienyl, triazinyl, triazolyl, xanthenyl, and the like.

[0034] "Cycloalkyl" refers to a saturated monocyclic or polycyclic alkyl group, which may be fused to 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, optionally 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, the heteroatoms may be the same or different. Heterocycloalkyl groups include, but are not limited to, azepanyl, azetidinyl, indolinyl, morpholinyl, piperazinyl, piperidinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydroquinolinyl, tetrahydroindazolyl, tetrahydroindolyl, tetrahydroisoquinolinyl, tetrahydropyranyl, tetrahydroquinoxalinyl, tetrahydrothiopyranyl, thiazolidinyl, thiomorpholinyl, thioxanthenyl, thioxanthyl, and 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 heterocycloalkynyl group contains more than one heteroatom, the heteroatoms may be the same or different.

[0040] A first aspect of the present invention 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 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 reagents 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 the groups is independently selected from the same or different ester groups, alkyl groups, heteroalkyl groups, hydrogen atoms, benzenesulfonyl groups, aryl groups, alkyl-substituted aryl groups, and alkoxy groups.

[0046] The first aspect of the embodiment of the present application provides a method for the addition of alkyl radicals and capture reagents, which oxidizes secondary alkylethylbenzene A through single electron transfer, and subsequent proton-coupled electron transfer (PCET) to induce carbon-carbon bond cleavage, and then reacts with capture reagent B to generate an addition product of alkyl radicals and capture reagents. Among them, acridine salt photocatalysts have a high oxidation potential and can oxidize neutral benzene rings, thereby promoting the reaction. The method for the addition of alkyl radicals and capture reagents provided in the embodiment of the present application realizes a method for generating alkyl radicals from linear unactivated secondary alkylethylbenzene, realizes a carbon-carbon bond cleavage method of secondary alkylethylbenzene that has not been realized before, and has a wide range of substrates. 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 reagents. This method represents a new method for expanding alkyl radical chemistry using secondary alkylethylbenzene. The generated alkyl radicals can be captured by a variety of capture reagents, including electron-deficient double bonds, heterocycles, and p-toluenesulfonyl cyanide. In addition, the reactant raw materials are easily accessible, and the reactants do not require additional modification before the reaction, so they can be directly used for preparation and production. The reaction process is safe and controllable, simplifying the operating steps and shortening the reaction route. This significantly reduces the production cost of preparing such captured addition products and greatly expands the designability and application prospects of such compounds. Furthermore, the addition products obtained by this method have high functionality, making them more diverse in the synthesis of pharmaceutical intermediates, functional materials, and metal ligand applications. They can be widely used in the synthesis of pharmaceutical intermediates, the preparation of chiral ligands and functional materials, and can effectively reduce the economic cost of preparing pharmaceutical intermediates and functional materials, while also providing environmental friendliness.

[0047] In some embodiments, the secondary alkylethylbenzene A and capture reagent B in step S10 can be prepared according to existing preparation methods or directly purchased commercially. The reactant raw materials are easily available and do not require additional modification before the reaction, so they can be directly used in the production process, simplifying the operation steps, shortening the reaction route, and reducing the production cost.

[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 light-induced reaction conditions include: reacting in an inert atmosphere at an irradiation wavelength of 400 nm to 480 nm for 24 to 48 hours. These reaction conditions are more conducive to promoting the oxidation of neutral benzene rings by the acridinium salt photocatalyst, oxidizing secondary alkylethylbenzene A through single electron transfer, thereby inducing carbon-carbon bond cleavage, and subsequently reacting with the capture agent B to form an addition product of the alkyl radical and the capture agent.

[0050] In some embodiments, in the addition product of secondary alkylethylbenzene A and alkyl radical with a 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 with a 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 with a 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-C5) 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, and purine.

[0054] In some embodiments, the capture agent B and the addition product of 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, the capture agent B and the addition product of 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, the capture agent B and the addition product of 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 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.

[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 ) Cycloalkyl may be cyclopropyl, cyclobutyl, cyclopentyl, etc.

[0060] In some embodiments, (C3-C20 )Heterocycloalkyl can 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 can 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 ) Cycloalkenyl may be cyclopropenyl, cyclobutenyl, cyclopentenyl, etc.

[0064] In some embodiments, (C3-C 20 )Heterocycloalkenyl 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 ) cycloalkynyl may be (C3-C 10 )cycloalkynyl, (C3-C5)cycloalkynyl, (C3-C4)cycloalkynyl, etc. In some specific embodiments, (C2-C 20 ) Cycloalkynyl may be cyclopropynyl, cyclobutynyl, cyclopentynyl, etc.

[0068] In some embodiments, (C3-C 20 ) heterocycloalkynyl 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 ) alkoxy 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 fused 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 phenyl group that is singly or multiple substituted at the ortho, meta, or para positions. 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 group shown. Wherein, when the substituent is an alkyl group, the alkyl group may be, but not limited to, methyl, ethyl, propyl, butyl, and isobutyl; when the substituent is a substituted alkyl group, the substituted alkyl group may be, but not limited to, trifluoromethyl, trichloromethyl, trifluoroethyl, and trichloroethyl; when the substituent is a halogen, the halogen may be, but not limited to, fluorine, chlorine, bromine, and iodine; when the substituent is an alkoxy group, the alkoxy group may be, but not limited to, methyloxy, ethyloxy, and 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, or thiophene.

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

[0074] In some embodiments, the aryloxy group can be phenoxy, naphthoxy, anthryloxy, or phenanthrenoxy.

[0075] In some embodiments, aryl (C1-C 20 ) alkyl may be aryl (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, 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 )alkyl can be (C2-C 10 )alkenyl (C1-C 10), (C2-C5) alkenyl (C1-C3). In some specific embodiments, the (C2-C 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 )alkyl can be (C2-C 10 )alkynyl(C1-C 10 )alkyl, (C2-C5)alkynyl (C1-C3)alkyl. In some specific embodiments, the (C2-C 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, cyano (C1-C 20 ) alkyl may be cyano (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 embodiments, the addition product of the alkyl radical and the capture agent comprises:

[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 all 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 ) alkyl group.

[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 acridinium 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. The oxidant and water are used for the addition reaction of free radicals and heterocycles.

[0089] In the embodiment of the present application, the content of the photocatalyst, oxidant and water is within a certain range of proportions, so that the reaction has a high catalytic efficiency and obtains a target product with a higher 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), which 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 for promoting 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 for promoting 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 selected based on a comprehensive screening process, including solubility, boiling point, and reactivity. Acetonitrile is preferred, as it exhibits good solubility for the secondary alkylethylbenzene A, the capture agent B, the acridinium salt photocatalyst, and the additive.

[0093] In a second aspect of the present application, an addition product of an alkyl radical and a capture agent prepared by the above method is provided. 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 the group consisting of an ester group, an alkyl group, a heteroalkyl group, a hydrogen atom, a phenylsulfonyl 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 reagent provided in the second aspect of the embodiment of the present application has high functionality and can be widely used in organic synthetic chemistry, biochemistry, asymmetric catalysis, pesticide and pharmaceutical research and other fields, such as the synthesis of drug intermediates, the preparation of functional materials, and the preparation of chiral ligands such as metal ligands.

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

[0096] At least one of .

[0097] In a third aspect of the embodiment of the present application, the addition product prepared by the above-mentioned addition method or the addition product of the above-mentioned alkyl radical and the capture agent is applied at least 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 reagent provided in the third aspect of the embodiment of the present application has high functionality and can provide raw materials or reaction intermediates for the synthesis of drug intermediates, the preparation of functional materials or the preparation of chiral ligands; it can provide diversified options for the synthesis of drug intermediates, functional materials and applications.

[0099] In order to make the above implementation details and operations of the present application 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 radical and the capture agent and the addition method thereof in the embodiments of the present application, the above technical solution is illustrated by 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 (0.01 mmol, 4.6 mg), the trapping reagent benzalmalononitrile (0.2 mmol, 30.8 mg) and the oxidant ammonium persulfate (0.5 mmol, 114 mg) were weighed into an oven-dried 8 mL vial equipped with a magnetic star bar. Acetonitrile and water (1 mL and 0.1 mL) were added, followed by the addition of secondary alkylethylbenzene ((1,2-dimethylpropyl)benzene, 0.4 mmol). The reaction vessel was degassed, backfilled with argon, and then placed under a Kessil lamp at 450 nm (40 W). The reaction progress was monitored by TLC. Upon completion, the reaction mixture was concentrated and purified by silica gel flash column chromatography to obtain the desired product in 81% yield.

[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 was exactly as described above in 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-propylhexan-2-yl)benzene and the capture 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 was exactly as described above in 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 capture reagent is benzalkonium dinitrile. 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 was exactly as described above in 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 capture reagent is benzalkonium dinitrile. 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 was exactly as described above in 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 capture reagent is benzalkonium dinitrile. 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 was exactly as described above in 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 capture reagent is benzalkonium dinitrile. 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 .99–1.82 (m, 2H), 1.70 (tdd, J=9.5, 6.6, 2.8Hz, 2H), 1.55–1.45 (m, 1H), 1.40 (tt, J=12.7, 3.6Hz, 1H), 1.26–1.04 (m, 3H), 0.91–0.76 (m, 1H). 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 was exactly as described above in 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 is similar to that of Example 1, except that the substrate is (1-(4,4-difluorocyclohexyl)ethyl)benzene and the capture reagent is benzalkonium dinitrile. 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 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 same as 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 capture reagent is benzalkonium dinitrile. 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 was exactly as described above in 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 is similar to that of Example 1, except that the capture reagent uses para-ester-substituted benzyl malononitrile and the secondary alkyl ethylbenzene A uses (3-propylhexan-2-yl)benzene. The yield of the target product is 89% and the DR ratio 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 was exactly the above molecular structure 10.

[0151] Example 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 is similar to that of Example 1, except that the capture reagent uses an ortho-ester-substituted benzalkonium dinitrile and the secondary alkyl ethylbenzene A uses (1-cyclohexylethyl)benzene. The yield of the target product is 89% and the dr ratio 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 was exactly the above 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 and irradiated (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 purification. Compound 12 yield 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 was exactly the above-mentioned molecular structure 12.

[0162] Example 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 refers to the preparation method of the compound in Example 1, except that the capture reagent is alkenyl sulfone, the capture reagent is 2.0 equivalents, and the secondary alkyl ethylbenzene A is (1-cyclohexylethyl)benzene.

[0166] The yield of the target product was 61%.

[0167] 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 was exactly the above-mentioned molecular structure 13.

[0168] Example 14

[0169] 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:

[0170]

[0171] The preparation method is similar to that of Example 1, except that the capture reagent used is cis-1,2-bis(phenylsulfonyl)ethylene, the capture reagent is 2.0 equivalents, and the secondary alkylethylbenzene A is (1-cyclohexylethyl)benzene. The yield of the target product is 58%.

[0172] 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 same as the above molecular structure 14.

[0173] Example 15

[0174] 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:

[0175]

[0176] The preparation method is similar to that of Example 1, except that the capture reagent used 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%.

[0177] 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 molecular structure 15.

[0178] Example 16

[0179] A (Z)-N-((4-acetylbenzyl)oxy)cyclohexaneiminocyanide compound, the structural formula of the (Z)-N-((4-acetylbenzyl)oxy)cyclohexaneiminocyanide compound is shown in the following molecular structural formula 16:

[0180]

[0181] The preparation method was similar to that of Example 1, except that 2.0 equivalents of (E)-N-((4-acetylbenzyl)oxy)-1-(phenylsulfonyl)carboximide cyanide was used as the capture reagent, and (1-cyclohexylethyl)benzene was used as the secondary alkylethylbenzene A. The yield of the target product was 46%.

[0182] 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 molecular structure 16.

[0183] Example 17

[0184] A (Z)-N-isopropoxytetrahydro-2H-pyran-4-methylenecarboxylic acid cyanide compound, the structural formula of the (Z)-N-isopropoxytetrahydro-2H-pyran-4-methylenecarboxylic acid cyanide compound is shown in the following molecular structural formula 17:

[0185]

[0186] The preparation method was similar to that of Example 1, except that 2.0 equivalents of (E)-N-isobutyloxy-1-(phenylsulfonyl)carboximide cyanide was used as the capture reagent, and 4-(1-phenylethyl)tetrahydro-2H-pyran was used as the secondary alkyl ethylbenzene A. The yield of the target product was 76%.

[0187] 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.

[0188] Example 18

[0189] 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:

[0190]

[0191] The preparation method is similar to that of Example 1, except that 2.0 equivalents of (E)-1-(phenylsulfonyl)-N-propoxycarboximide cyanide are used as the capture reagent, and (1-phenylethyl)cycloheptane is used as the secondary alkyl ethylbenzene A. The yield of the target product is 75%.

[0192] 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 was exactly the above-mentioned molecular structure 18.

[0193] Example 19

[0194] A (1's, 4'r)-4'-pentyl-[1,1'-bis(cyclohexane)]-4-carbonitrile compound, wherein the structural formula of the ((1's, 4'r)-4'-pentyl-[1,1'-bis(cyclohexane)]-4-carbonitrile is shown in the following molecular structural formula 19:

[0195]

[0196] The preparation method is similar to that of Example 1, except that 2.0 equivalents of p-toluenesulfonyl cyanide are used as the capture reagent, and (1s,4r)-4-pentyl-4'-(1-phenylethyl)-1,1'-bis(cyclohexane) is used as the secondary alkyl ethylbenzene A. The yield of the target product is 67%, and the DR ratio is 1:1.

[0197] 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 was exactly as described above in molecular structure 19.

[0198] The above description is only a preferred embodiment of the present application and is not intended to limit the present application. Any modifications, equivalent replacements and improvements made within the spirit and principles of the present application should be included in the scope of protection 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: A secondary alkyl ethylbenzene A, a capture agent B, an acridinium salt photocatalyst, and an additive are dissolved in an organic solvent and subjected to a light irradiation reaction to obtain an addition product of an alkyl radical and the capture agent; the molar ratio of the acridinium salt photocatalyst, the additive, the secondary alkyl ethylbenzene A, and the capture agent B is (0.1-20):(0.1-20):(0.2-40):(1-100); and the light irradiation reaction is carried out in an inert atmosphere at an irradiation wavelength of 400 nm to 480 nm for 24 to 48 hours; Wherein, the general structural formula of the secondary alkyl ethylbenzene A is: The capture agent B is selected from The structural formula of the addition product of the alkyl radical and the capture agent is: Among them, R 1 is a hydrogen atom, R 2 Selected from C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C3-C 10 Any of the heterocycloalkyl groups, R 6 Selected from C1-C 10 Any of alkyl and phenyl; The acridinium salt photocatalyst is selected from Mes-Acr-PhBF4, The additive is selected from at least one of an oxidant, a Bronsted acid, and water.

2. The method for adding an alkyl radical to a capture agent according to claim 1, wherein: The organic solvent is selected from at least one of acetonitrile, nitromethane, dichloromethane, and 1,2-dichloromethane; And / or, the capture agent B is selected from at least one of (E)-N-((4-acetylbenzyl)oxy)-1-(phenylsulfonyl)formimide cyanide, (E)-N-isobutoxy-1-(phenylsulfonyl)formimide cyanide, and (E)-1-(phenylsulfonyl)-N-propoxyformimide cyanide.

3. The method for adding an alkyl radical to a capture agent according to claim 2, wherein: The oxidant is selected from at least one of persulfate, high-valent iodine, quinone, potassium permanganate, peroxide, oxygen, and N-fluorobenzenesulfonimide; And / or, the Bronsted acid is selected from at least one of acetic acid, fluoroacetic acid, sulfuric acid, hydrochloric acid, perchloric acid, phosphoric acid, and nitric acid.

4. The method for adding an alkyl radical to a capture agent according to any one of claims 1 to 3, wherein: The heterocycle is selected from any one of quinoline, pyridine, thiazole, benzothiazole, pyrazine, pyrimidine and purine.

5. The method for adding an alkyl radical to a capture agent according to claim 4, wherein: The R 1 is a hydrogen atom, the R 2 Any one selected from C1-C5 alkyl, C3-C5 cycloalkyl, C3-C5 heterocycloalkyl; and / or, the R 6 Any one selected from C1-C5 alkyl and phenyl.

6. The method for adding an alkyl radical to a capture agent according to claim 5, wherein: The secondary alkylethylbenzene A is selected from at least one of (1-cyclohexylethyl)benzene, 4-(1-phenylethyl)tetrahydro-2H-pyran, and (1-phenylethyl)cycloheptane.

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