KR101469126B1 - Method for preparing of epoxide compound and method for preparing of aziridine compound - Google Patents

Abstract

The present invention relates to a method for preparing an epoxide compound and a method for preparing aziridine compound. More specifically, the present invention relates to a method for preparing an epoxide compound and a method for preparing an aziridine compound which simplifies the reaction with a soft condition in the presence of visible ray and photocatalyst and has high yield to have high economical feasibility.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a method for preparing an epoxide compound and an aziridine compound,

The present invention relates to a process for preparing an epoxide compound and a process for preparing an aziridine compound. More particularly, the present invention relates to a process for preparing an epoxide compound and a process for preparing an aziridine compound, which have a high yield and a high economic efficiency, while simplifying the reaction using a photocatalyst.

Since trifluoromethyl (CF ₃₎ a compound comprising a group is represented by the unique properties etc. pesticide, pharmaceutical and material field that value, the size in the industrial use, the study of organic fluorine chemistry to be introduced into the methyl group, trifluoromethyl compound It has been known as an important task for the time being.

More specifically, the introduction of a trifluoromethyl group into a medicament or an agricultural chemical improves the activity such as metabolic stability, lipophilicity, bioavailability, and binding selectivity Which has attracted great interest in the field of medicine and agriculture.

On the other hand, epoxide and aziridine compounds are interesting compounds because of their wide variety of applications and can be used as versatile intermediates in subsequent reactions. In particular, epoxides and aziridines, including CF ₃ , can be converted into various components through a ring opening reaction, but it is difficult to synthesize compounds containing CF ₃ by other methods.

However, as an example of making an epoxide compound containing CF ₃ from allyl alcohol in one step, two examples using palladium and copper as a catalyst are known as the following reaction formula (Chem.Lett. 1987, 521, J. Am Chem. Soc., 2012, 134, 12462), an example of synthesizing an aziridine containing CF ₃ from allylamine is not yet known.

The present invention provides a process for producing an epoxide compound and a process for producing an aziridine compound which can realize a high yield under simple conditions under visible light and a photocatalyst under a gentle condition, .

According to the present invention,

Preparing a reaction mixture comprising an allyl alcohol compound represented by the following formula (1), an iodofluoro compound represented by the following formula (2), a reducing agent, and a photocatalyst; And

And a step of irradiating the reaction mixture with visible light. The present invention also provides a process for producing an epoxide compound represented by the following formula (3).

[Chemical Formula 1]

(2)

(3)

In the general formulas (1) and (3), R1 is a hydrocarbyl group or a heterohydrocarbyl group,

In Formula 2, n is an integer of 1 to 10.

The present invention also provides a method for preparing a photoresist composition, comprising: preparing a reaction mixture comprising an allylamine compound represented by the following general formula (4), an iodofluoro compound represented by the following general formula (2), a reducing agent, and a photocatalyst; And a step of irradiating the reaction mixture with visible light. The present invention also provides a process for producing an aziridine compound represented by the following formula (5).

[Chemical Formula 4]

(2)

[Chemical Formula 5]

In the above formulas (4) and (5), R2 is a hydrocarbyl group or a heterohydrocarbyl group,

In Formula 2, n is an integer of 1 to 10.

According to the present invention, there can be provided a process for producing an epoxide compound and a process for producing an aziridine compound, which can realize a high yield while simplifying the reaction under mild conditions under visible light and photocatalyst, Can be provided.

The epoxide compound or the aziridine compound containing a fluoroalkyl group prepared by the production method of the present invention can be utilized in various fields such as medicine, medicine, pesticide, and material field.

Hereinafter, a method for preparing an epoxide compound and a method for preparing an aziridine compound according to a specific embodiment of the present invention will be described in detail.

First, a process for preparing an epoxide compound of the present invention comprises: preparing a reaction mixture comprising an allyl alcohol compound represented by the following formula (1), an iodofluoro compound represented by the following formula (2), a reducing agent, and a photocatalyst; And irradiating the reaction mixture with visible light, wherein the epoxide compound is represented by the following formula (3).

[Chemical Formula 1]

(2)

(3)

In the general formulas (1) and (3), R1 is a hydrocarbyl group or a heterohydrocarbyl group,

In Formula 2, n is an integer of 1 to 10.

In the process for producing an epoxide compound of the present invention, more specifically, the photocatalyst acts together with a visible light and a reducing agent to form C _n F _{2n +1} I as a C _n F _{2n + 1} radical And the C _n F _{2n + 1} radical may be reacted with an alkene double bond to form a C _n F _{2n +1} substituted intermediate.

Then, the intermediate may undergo nucleophilic reaction by a reducing agent, which is a base, to finally form an epoxide compound into which a C _n F _{2n +1} group is introduced.

[Reaction Scheme 1]

In Formula 2, n is an integer of 1 to 10, preferably an integer of 1 to 5.

In the process for producing an epoxide compound according to the present invention as described above, the substituent R 1 is a hydrocarbyl group or a heterohydrocarbyl group substituted with various functional groups, and is not particularly limited to the kind, and exhibits high reactivity and yield, It can be widely applied to compounds.

According to one embodiment of the present invention, R < 1 > is, for example, alkyl of 1 to 20 carbon atoms; Aryl having 6 to 20 carbon atoms; Alkylaryl having 7 to 20 carbon atoms; Or arylalkyl having 7 to 20 carbon atoms; Alkoxy having 1 to 20 carbon atoms; Aryloxy having 6 to 20 carbon atoms; Alkoxyaryl having 6 to 20 carbon atoms; Cycloalkyl having 3 to 20 carbon atoms; Heterocycloalkyl having 3 to 20 carbon atoms; Or heteroaryl having 6 to 20 carbon atoms; Silylalkyl of 1 to 20 carbon atoms; Alkylsilyl having 1 to 20 carbon atoms; Or a silyl ether having 1 to 20 carbon atoms, but the present invention is not limited thereto, and the process for producing the epoxide compound of the present invention has an advantage that it can be applied without being limited by the kind of the substituent R1.

The R 1 may or may not contain one or more functional groups selected from the group consisting of halogen, hydroxy, alkoxy, ether, ester, ketone, aldehyde, carbonate, and sulfonate.

In the production method of the epoxide compounds of the present invention, the photocatalyst is a substance that accepts a light promotes a chemical reaction, under visible light, creating a C _n F _{2n +1} I _n F _{2n + 1} radical in the C formula An allyl alcohol compound represented by the formula (1) can be formed from an epoxide compound into which a fluoroalkyl group has been introduced.

The photocatalyst may include a ruthenium or iridium, and specific examples include _{Ir (ppy) 3, [Ir} (ppy) 2 (dtb-bpy)] PF 6, [Ru (bpy) 3] Cl 2, [Ru (Cl-phen) ₃ ] (PF ₆ ) ₂ , or [Ru (Phen) ₃ ] Cl ₂ . In particular, [Ru (bpy) ₃ ] Cl ₂ and [Ru (Phen) ₃ ] Cl ₂ are less expensive and may be preferable to iridium catalysts.

In the process for preparing the epoxide compound of the present invention, the reaction mixture may contain DBU (1,8-diazabicyclo- [5,4,0] -un-dec-7-ene) as a reducing agent.

The DBU can serve both as a reducing agent in the photocatalytic reaction and as a base in the nucleophilic reaction of alcohol. Therefore, by reacting DBU having two functions as described above with an allyl alcohol compound, it is possible to easily form an epoxide compound containing a fluoroalkyl group from an allyl alcohol compound without using various reaction additives and complicated processes, Cost and production cost of the final product can be reduced.

The reaction mixture may further contain a solvent. Specific examples of the solvent include DMF, CH ₃ CN, CH ₂ Cl ₂ , MeOH, EtOH or a mixture thereof. The solvent can be easily mixed by dissolving the reaction mixture, and the intermediate C _n F The concentration of _{2n + 1} radicals can be maintained appropriately to help the reaction. The concentration of the solvent is about 0.1 to about 2 mol, which is preferable because it can help the progress of the reaction and fulfill the role of the solvent.

Further, in the step of mixing the allyl alcohol compound with a reducing agent and an iodofluoro compound, the molar ratio of the allyl alcohol compound: reducing agent: iodofluoro compound may be 1: 1 to 3: 1 to 5. It is preferable that the reducing agent and the iodofluoro compound are contained in an amount of 1 mole or more per mole of the allyl alcohol compound in order to increase the reaction yield. Particularly, the iodofluoro compound reacting with the allyl alcohol compound in a ratio of 1: It is preferable that it contains an excessive amount of 2 to 5 moles relative to 1 mole of the allyl alcohol compound. When the reducing agent and the iodofluoro compound are contained in an amount less than the above range, the reaction is not terminated and the reaction yield may be low.

The photocatalyst may include about 0.0001 to about 1 mol%, more preferably about 0.01 to about 1 mol%, of the reaction mixture containing the allyl alcohol compound, the reducing agent, and the iodofluoro compound. The photocatalyst is a material that receives light in the visible light region to promote a chemical reaction and remains as it is before and after the reaction. Even in a small amount of the above range, the reaction can be sufficiently promoted, and the economical efficiency of the reaction can be enhanced.

Next, the reaction mixture is irradiated with visible light to proceed the reaction.

In addition, the step of irradiating the visible light may use a general incandescent lamp, a fluorescent lamp, a blue LED and the like as well as sunlight, and the reaction mixture containing the allyl alcohol compound, the iodofluoro compound, the reducing agent and the photocatalyst, It is possible to irradiate visible light. The visible light may then be irradiated with the reaction mixture for about 10 minutes to about 10 hours, preferably about 1 hour to about 5 hours.

As described above, the method of forming an epoxide compound by irradiating a visible light to a reaction mixture containing an allyl alcohol compound, an iodofluoro compound, a reducing agent and a photocatalyst does not require special conditions such as temperature and pressure, Or under conditions known to be commonly used in the introduction reaction of a specific functional group. In particular, the method can be carried out under mild conditions of room temperature and normal pressure, so that the allyl alcohol compound can be more easily converted into the fluoroalkyl group-introduced epoxide compound.

According to another embodiment of the present invention, there is provided a process for preparing a photoresist composition, comprising: preparing a reaction mixture comprising an allylamine compound represented by the following formula (4), an iodofluoro compound represented by the following formula (2), a reducing agent, and a photocatalyst; And a step of irradiating the reaction mixture with visible light. The present invention also provides a process for producing an aziridine compound represented by the following formula (5).

[Chemical Formula 4]

(2)

[Chemical Formula 5]

In the above formulas (4) and (5), R2 is a hydrocarbyl group or a heterohydrocarbyl group,

In Formula 2, n is an integer of 1 to 10.

In the process for preparing an aziridine compound according to the present invention as described above, the substituent R2 is a hydrocarbyl group or a heterohydrocarbyl group substituted with various functional groups and is not particularly limited to a specific kind, and exhibits high reactivity and yield, It can be widely applied to compounds.

According to one embodiment of the present invention, R 2 in Formula 4 is alkyl having 1 to 20 carbon atoms; Aryl having 6 to 20 carbon atoms; Alkylaryl having 7 to 20 carbon atoms; Or arylalkyl having 7 to 20 carbon atoms; Alkoxy having 1 to 20 carbon atoms; Aryloxy having 6 to 20 carbon atoms; Alkoxyaryl having 6 to 20 carbon atoms; Cycloalkyl having 3 to 20 carbon atoms; Heterocycloalkyl having 3 to 20 carbon atoms; Or heteroaryl having 6 to 20 carbon atoms; Silylalkyl of 1 to 20 carbon atoms; Alkylsilyl having 1 to 20 carbon atoms; Or a silyl ether having 1 to 20 carbon atoms, but the present invention is not limited thereto, and the process for preparing an aziridine compound of the present invention has an advantage that it can be applied without being limited by the kind of the substituent R2.

The R2 may or may not contain one or more functional groups selected from the group consisting of halogen, hydroxy, alkoxy, ether, ester, ketone, aldehyde, carbonate, and sulfonate.

In Formula 2, n is an integer of 1 to 10, preferably an integer of 1 to 5.

In the production method of the aziridine compound of the present invention, the photocatalyst is a substance that accepts a light promotes a chemical reaction, under visible light, creating a C _n F _{2n +1} I _n F _{2n + 1} radical in the C formula 4 can be formed from an aziridine compound into which a fluoroalkyl group is introduced.

The photocatalyst may include a ruthenium or iridium, and specific examples include _{Ir (ppy) 3, [Ir} (ppy) 2 (dtb-bpy)] PF 6, [Ru (bpy) 3] Cl 2, [Ru (Cl-phen) ₃ ] (PF ₆ ) ₂ , and [Ru (Phen) ₃ ] Cl ₂ . In particular, [Ru (bpy) ₃ ] Cl ₂ and [Ru (Phen) ₃ ] Cl ₂ are less expensive and may be preferable to iridium catalysts.

In the preparation of the aziridine compound of the present invention, the reaction mixture may contain TMEDA (N, N, N ', N'-tetramethylethylenediamine) as a reducing agent.

The TMEDA can serve both as a reducing agent in the photocatalytic reaction and as a base in the nucleophilic reaction of amines. Therefore, by reacting TMEDA having two functions as described above with an allyl amine compound, it is possible to easily form an aziridine compound containing a fluoroalkyl group from an allyl alcohol compound without using various reaction additives and complicated processes, Cost and production cost of the final product can be reduced.

The reaction mixture may further contain a solvent. Specific examples of the solvent include DMF, CH ₃ CN, CH ₂ Cl ₂ , MeOH, EtOH or a mixture thereof. The solvent can be easily mixed by dissolving the reaction mixture, and the intermediate C _n F The concentration of _{2n + 1} radicals can be maintained appropriately to help the reaction. The concentration of the solvent is about 0.1 to about 2 mol, which is preferable because it can help the progress of the reaction and fulfill the role of the solvent.

Further, in the step of mixing the allylamine compound with a reducing agent and an iodofluoro compound, the molar ratio of the allylamine compound: reducing agent: iodofluoro compound may be 1: 1 to 3: 1 to 5. It is preferable that the reducing agent and the iodofluoro compound are contained in an amount of 1 mole or more based on 1 mole of the allylamine compound in order to increase the reaction yield. In particular, the iodofluoro compound reacting with the allylamine compound in a ratio of 1: It is preferable that it contains an excessive amount of 2 to 5 moles relative to 1 mole of the allylamine compound. If the reducing agent and the iodofluoro compound are contained in an amount less than the above range, the reaction is not terminated and the reaction yield may be low.

The photocatalyst may include about 0.0001 to about 1 mol%, more preferably about 0.01 to about 1 mol%, based on the reaction mixture containing the allylamine compound, the reducing agent, and the iodofluoro compound. The photocatalyst is a material that receives light in the visible light region to promote a chemical reaction and remains as it is before and after the reaction. Even in a small amount of the above range, the reaction can be sufficiently promoted, and the economical efficiency of the reaction can be enhanced.

Next, the reaction mixture is irradiated with visible light to proceed the reaction.

In addition, the step of irradiating the visible light may use a general incandescent lamp, a fluorescent lamp, a blue LED and the like as well as sunlight, and the reaction mixture containing the allylamine compound, the iodofluoro compound, the reducing agent and the photocatalyst may be used as an incandescent lamp It is possible to irradiate visible light. The visible light may then be irradiated with the reaction mixture for about 10 minutes to about 5 hours, preferably about 1 hour to about 2 hours.

As described above, the method of forming an aziridine compound by irradiating a visible light to a reaction mixture containing an allylamine compound, an iodofluoro compound, a reducing agent, and a photocatalyst does not require special conditions such as temperature and pressure, Or under conditions known to be commonly used in the introduction reaction of a specific functional group. In particular, the method can proceed under mild conditions of room temperature and normal pressure, so that the allylamine compound can be more easily converted into the aziridine compound into which the fluoroalkyl group is introduced.

Hereinafter, the present invention will be described in more detail in the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

< Example >

Epoxide  Preparation of compounds

Example  One

oct-1-en-3- ol (0.2 mmol) to fill the Ir (ppy) ₃ test tubes (0.5 mol% for the entire reaction _{mixture), CH 3 CN (0.8 mL} , 0.25M), DBU (0.4 mmol, 2 equiv.) was added and CF ₃ I (0.6 mmol, 3 equiv.) was injected. The test tube was placed under a 14 W incandescent lamp at room temperature and reacted at room temperature for 3 hours.

The yield of 2-pentyl-3- (2,2,2-trifluoroethyl) oxirane thus prepared was measured by ¹⁹ F NMR spectroscopy using 4-fluorotolune as an internal standard or by pure separation through a silica gel column Respectively.

Example  2

The Ir (ppy) ₃ 0.5 mol% instead of Catalyst _{[Ir (ppy) 2 (dtb} -bpy)] PF 6 0.5 mol%, and the yield was measured.

Example  3

The catalyst was replaced with [Ru (bpy) ₃ ] Cl ₂ instead of 0.5 mol% of Ir (ppy) ₃ 0.5 mol%, and the yield was measured.

Example  4

Except that 0.5 mol% of [Ru (Cl-phen) ₃ ] (PF ₆ ) _{2 was} used instead of 0.5 mol% of Ir (ppy) _{3 as a} catalyst.

Example  5

The catalyst was replaced with [Ru (Phen) ₃ ] Cl ₂ instead of 0.5 mol% of Ir (ppy) ₃ 0.5 mol%, and the yield was measured.

Example  6 to 16

Except that other allyl alcohol compounds were used in place of oct-1-en-3-ol as a reactant or other iodofluoro compounds were used in place of CF ₃ I, and the yields were measured . The allyl alcohol compounds and the iodofluoro compounds used in Examples 6 to 16 are shown in Table 1 below.

Comparative Example  One

The procedure of Example 1 was repeated except that the photocatalyst was not used, and the yield was measured.

Comparative Example  2

The procedure of Example 3 was repeated except that no visible light was irradiated, and the yield was measured.

The main reaction conditions of Examples 1 to 16 and Comparative Examples 1 and 2 are shown in Table 1 below.

Example no. Allyl alcohol compound Iodofluoro compounds and amounts used Photocatalyst Example 1

CF ₃ I (3 equiv.) Ir (ppy) ₃ Example 2

CF ₃ I (3 equiv.) [Ir (ppy) ₂ (dtb-bpy)] PF ₆ Example 3

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 4

CF ₃ I (3 equiv.) _{[Ru (Cl-phen) 3} ] (PF 6) 2 Example 5

CF ₃ I (3 equiv.) [Ru (Phen) ₃ ] Cl ₂ Example 6

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 7

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 8

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 9

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 10

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 11

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 12

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 13

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 14

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 15

C ₃ F ₇ I (2 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 16

C ₄ F ₉ I (2 equiv.) [Ru (bpy) ₃ ] Cl ₂ Comparative Example 1

CF ₃ I (3 equiv.) Not used Comparative Example 2

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂
(No light)

The yields of Examples 1 to 16 and Comparative Examples 1 to 2 are shown in Table 2 below.

Example no. yield(%) Example 1 65 Example 2 60 Example 3 86 Example 4 70 Example 5 80 Example 6 85 Example 7 88 Example 8 83 Example 9 80 Example 10 81 Example 11 91 Example 12 85 Example 13 82 Example 14 90 Example 15 77 Example 16 84 Comparative Example 1 0 Comparative Example 2 0

As shown in Table 2, when the allyl alcohol compound was converted into the fluoroalkyl group-introduced epoxide compound by using the photocatalyst and the visible light according to the manufacturing method of the present invention, While simplifying the reaction, it showed a high yield of 70% or more.

In addition, it can be expected to be used in the production of various epoxide compounds depending on the application because it shows a high yield regardless of the kind of substituent.

On the other hand, in Comparative Example 1 which does not include a photocatalyst or Comparative Example 2 in which a photocatalyst was contained but no visible light was irradiated, the yield was 0, indicating that the reaction did not proceed.

Preparation of aziridine compounds

Example  17

[Ru (bpy) ₃ ] Cl ₂ (0.5 mol% with respect to the total reaction mixture), CH ₃ CN (4 mL, 0.25 M), and N 2 O were added to a test tube filled with N- benzylprop-2-en- In the TMEDA (2.0 mmol, 2 equiv. ) , followed by injection of _{CF 3 I (. 3.0 mmol,} 3 equiv). The test tube was placed under a 14 W incandescent lamp at room temperature and reacted at room temperature for 2 hours.

The yield of 1-benzyl-2- (2,2,2-trifluoroethyl) aziridine obtained was measured by ¹⁹ F NMR spectroscopy using 4-fluorotolune as an internal standard.

Example  18 to 21

Except that an allylamine compound was used in place of N- benzylprop-2-en-1-amine as a reactant or another iodofluoro compound was used in place of CF ₃ I, and the yield was Respectively.

The main reaction conditions of Examples 17 to 21 are shown in Table 3 below.

Allylamine compound Iodofluoro compounds and amounts used Photocatalyst Example 17

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 18

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 19

CF ₃ I (3 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 20

C ₃ F ₇ I (2 equiv.) [Ru (bpy) ₃ ] Cl ₂ Example 21

C ₄ F ₉ I (2 equiv.) [Ru (bpy) ₃ ] Cl ₂

The yields of Examples 17 to 21 are shown in Table 4 below.

Example yield(%) Example 17 65 Example 18 61 Example 19 60 Example 20 55 Example 21 57

As shown in Table 4, when an allylamine compound was converted to an aziridine compound having a fluoroalkyl group introduced therein by using a photocatalyst and a visible ray according to the manufacturing method of the present invention, While the reaction was simplified, the yield was 55% or more.

In addition, it can be expected to be used in the production of various aziridine compounds depending on applications because it shows a high yield irrespective of kinds of substituents.

Claims (14)

An allyl alcohol compound represented by the following formula (1), an iodofluoro compound represented by the following formula (2); DBU (1,8-diazabicyclo- [5,4,0] -un-dec-7-ene); And _{Ir (ppy) 3, [Ir} (ppy) 2 (dtb-bpy)] PF 6, [Ru (bpy) 3] Cl 2, [Ru (Cl-phen) 3] (PF 6) 2, and [Ru (Phen) ₃ ] Cl &lt; ₂ &gt;); And
A process for producing an epoxide compound represented by the following formula (3), which comprises irradiating the reaction mixture with visible light:
[Chemical Formula 1]

(2)

(3)

In the above formulas (1) and (3)
R1 is alkyl of 1 to 20 carbon atoms; Aryl having 6 to 20 carbon atoms; Alkylaryl having 7 to 20 carbon atoms; Arylalkyl having 7 to 20 carbon atoms; Aryloxy having 6 to 20 carbon atoms; Alkoxyaryl having 6 to 20 carbon atoms; Heterocycloalkyl having 3 to 20 carbon atoms; Heteroaryl having 6 to 20 carbon atoms; Or a silyl ether having from 1 to 20 carbon atoms and wherein R 1 is selected from the group consisting of halogen, hydroxy, alkoxy, ether, ester, ketone, aldehyde, carbonate, and sulfonate,
In Formula 2,
n is an integer of 1 to 10;
delete delete delete delete The method according to claim 1,
Wherein the reaction mixture further comprises at least one solvent selected from the group consisting of DMF, CH ₃ CN, CH ₂ Cl ₂ , MeOH, and EtOH.
The method according to claim 1,
Wherein the photocatalyst is contained in an amount of 0.0001 to 1 mol% with respect to the reaction mixture.
An allylamine compound represented by the following formula (4), an iodofluoro compound represented by the following formula (2); TMEDA (N, N, N ', N'-tetramethylethylenediamine); And _{Ir (ppy) 3, [Ir} (ppy) 2 (dtb-bpy)] PF 6, [Ru (bpy) 3] Cl 2, [Ru (Cl-phen) 3] (PF 6) 2, and [Ru (Phen) ₃ ] Cl &lt; ₂ &gt;); And
A method for producing an aziridine compound represented by the following formula (5), which comprises irradiating the reaction mixture with visible light:
[Chemical Formula 4]

(2)

[Chemical Formula 5]

In the above formulas (4) and (5)
R2 is alkyl of 1 to 20 carbon atoms; Aryl having 6 to 20 carbon atoms; Alkylaryl having 7 to 20 carbon atoms; Arylalkyl having 7 to 20 carbon atoms; Or heterocycloalkyl having 3 to 20 carbon atoms and wherein R2 is optionally substituted with one or more functional groups selected from the group consisting of halogen, hydroxy, alkoxy, ether, ester, ketone, aldehyde, carbonate, and sulfonate ,
In Formula 2,
n is an integer of 1 to 10;
delete delete delete delete 9. The method of claim 8,
Wherein the reaction mixture further comprises at least one solvent selected from the group consisting of DMF, CH ₃ CN, CH ₂ Cl ₂ , MeOH, and EtOH.
9. The method of claim 8,
Wherein the photocatalyst is contained in an amount of 0.0001 to 1 mol% with respect to the reaction mixture.