CN112679435B - Alkylation/acylation method adopting photo-oxidation reduction/copper co-catalysis - Google Patents
Alkylation/acylation method adopting photo-oxidation reduction/copper co-catalysis Download PDFInfo
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Abstract
The invention discloses a photo-oxidation-reduction/copper co-catalysis alkylation/acylation method. The method uses novel diacyl peroxide as an alkylation/acylation reagent, introduces different alkyl (secondary alkyl) or acyl (tertiary alkyl) into various nitrogen-containing nucleophiles under the common catalysis condition of copper catalysis and a photoredox catalyst, and has the advantages of mild and simple reaction condition, economy, cheapness, excellent yield and good adaptability of reaction substrates.
Description
Technical Field
The application belongs to the technical field of organic synthesis, and particularly relates to decarboxylation C (sp) of diacyl peroxide and nitrogen-containing nucleophilic reagent mediated by free radicals under the condition of photo-oxidation-reduction/copper co-catalysis3) -N cross-coupling reaction process.
Background
In the last decades, the construction of C-N bonds, where C (sp) has been an important area of organic synthesis, has been the focus of the important role of C-N bonds in pharmaceuticals, natural products and pesticides3) The formation of the-N bond has attracted considerable attention. Thus, many form C (sp)3) Strategies for the-N bond include coupling of nitrogen nucleophiles with alkyl electrophiles (e.g., aliphatic halides, alcohols, etc.), reductive amination, hydroamination of olefins, and carboamination of olefins. Although great success has been achieved, this available method is still limited by the use of strong bases, the narrow reaction substrate range and the large amount of waste generated by the process.
Aliphatic carboxylic acids and their derivatives are inexpensive, stable, low-toxic and readily available, and are widely found in natural products and pharmaceuticals, thereby rendering free radical decarboxylation alkylation reactions for the rapid construction of C (sp)3) -X (X ═ C, N, O, S, etc.) bond. In 2017, the Fu, Peters topic group developed a decarboxylation C (sp) of an alkyl N-hydroxyphthalimide3) -N cross-coupling reaction, preparation of alkylphthalimide by one-electron reduction of copper complex under light conditions (see j.am. chem. soc.2017,139, 12153.). In 2018, the Macmillan topic group (see nature.2018,559,83.) and the Hu topic group (Nat cat.2018, 1,120.) independently reported dual copper-catalyzed and photo-redox-catalyzed decarboxylation C (sp)3) -N cross-coupling reactions using alkyl NHP esters and iodomesitylene dicarboxylates as alkyl precursors, respectively. According to these results, an alkylcarboxylic acid precursor compound such as N-hydroxyphthalic acidImine alkyl ester and iodo-mesitylene dicarboxylic acid ester are subjected to single electron reduction under the catalysis of photooxidation reduction or transition metal to form alkyl radical intermediate, and the alkyl radical intermediate is easily reacted with LnCunReacting the X-nitrogen nucleophilic complex A.
Although in decarboxylation C (sp)3) The N-coupling has achieved enormous success, but is limited by the source and scope of the alkylation substrate, and there is still a great need in the art for a novel alkylating reagent to achieve C (sp)3) Construction of the N bond. Diacyl peroxides are a class of redox active esters that can be readily prepared from aliphatic carboxylic acids and readily decarboxylated to provide alkyl groups under inexpensive transition metal catalysis and heat. Inspired by these pioneering efforts, we hypothesized that if an oxidative diacyl peroxide can generate alkyl radicals under photo-redox catalysis or copper catalysis, the alkyl radical species can further react with LnCunThe X-nitrogen nucleophilic complex A reacts to establish C (sp)3) -a N bond. However, the inventors have found that when a secondary or tertiary alkyl diacyl peroxide is used as the alkylating agent, it is difficult to form the corresponding radical intermediate, and hence the corresponding alkylated product, in transition metal catalyzed/heated/photoredoxed catalysis alone. Here we have developed a novel decarboxylation C (sp) of secondary or tertiary alkyl diacyl peroxides with nitrogen nucleophiles3) -N cross-coupling under photoredox/copper co-catalytic conditions provides a variety of alkylated or acylated nitrogen nucleophiles, including indazoles, triazoles, indoles, purines, carbazoles, anilines, sulfonamides, and other nitrogen nucleophiles.
Disclosure of Invention
The present invention aims to overcome the disadvantages of the prior art and to provide a photo-redox/copper co-catalyzed alkylation/acylation process. The method uses novel diacyl peroxide as an alkylation/acylation reagent, introduces different alkyl (secondary alkyl) or acyl (tertiary alkyl) into various nitrogen-containing nucleophiles under the common catalysis condition of copper catalysis and a photoredox catalyst, and has the advantages of mild and simple reaction condition, economy, cheapness, excellent yield and good adaptability of reaction substrates.
According to the invention, the photo-oxidation-reduction/copper co-catalysis alkylation/acylation method comprises the following steps:
adding a nitrogen-containing nucleophilic reagent shown in a formula 1, a diacyl peroxide shown in a formula 2, a photooxidation-reduction catalyst, a copper catalyst, a nitrogen-containing or phosphorus-containing organic ligand and an organic solvent into a reactor, then replacing the atmosphere in the reactor with an inert atmosphere, placing the reactor under illumination and stirring at 60-120 ℃ for reaction, and after the reaction is completed, carrying out post-treatment to obtain a target product shown in a formula 3. The reaction formula is as follows:
in the above reaction formula, R1,R2Independently of one another, from hydrogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-20Cycloalkyl, substituted or unsubstituted C6-20Aryl, substituted or unsubstituted C2-20Heteroaryl, substituted or unsubstituted C6-20An arylsulfonyl group; or R1,R2Are connected to each other and to the connection R1,R2Together form C with or without other hetero atoms2-20The heterocyclic structure of (a), said heterocyclic structure being optionally substituted with a substituent. Wherein R is1,R2Not simultaneously selected from hydrogen.
R3-R5Independently of one another, from hydrogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-20Cycloalkyl, substituted or unsubstituted C6-20An aryl group; or R3、R4And/or R5Together forming a substituted or unsubstituted C with or without heteroatoms3-20A cyclic group.
And wherein: n is 0 or 1;
when n is 0, R3、R4、R5One of which is selected from hydrogen;
when n is 1, R3、R4、R5Are not hydrogen.
Preferably, R1,R2Independently of one another, from hydrogen, methyl, substituted or unsubstituted phenyl, substituted or unsubstituted phenylsulfonyl; or R1,R2Are connected to each other and to the connection R1,R2Together form C with or without other hetero atoms2-12The heterocyclic structure of (a), said heterocyclic structure being optionally substituted with a substituent. Wherein R is1,R2Not simultaneously selected from hydrogen.
R3-R5Independently of one another, from hydrogen, methyl, ethyl, phenyl, substituted or unsubstituted propyl; or R3、R4And/or R5Together forming a substituted or unsubstituted C with or without heteroatoms3-8A cyclic group.
And wherein: n is 0 or 1;
when n is 0, R3、R4、R5One of which is selected from hydrogen;
when n is 1, R3、R4、R5Are not hydrogen.
In any part herein, the substituents of said "substituted or unsubstituted" and of the aforementioned heterocyclic ring structure are selected from the group consisting of halogen, -CN, -NO2、C1-6Alkyl radical, C1-6Alkoxy, -CHO, phenyl, halophenyl, C1-6Alkyl-substituted phenyl, C1-6Alkoxy-substituted phenyl, 2-methylaminocarbonyl-4-pyridyloxy, C3-8Cycloalkyl radical, C2-12Alkynyl, C2-12Alkenyl, benzoyl, C1-6Alkoxycarbonyl group, C1-6Alkyl-substituted phenoxy.
In any of the moieties herein, the heteroatom is selected from N, O or S.
Most preferably, the nitrogen-containing nucleophile represented by formula 1 is selected from compounds having the following structure:
the diacyl peroxide represented by formula 2 is selected from compounds having the following structures:
the aforementioned method according to the present invention, wherein the copper catalyst is selected from the group consisting of CuBr, Cu (OTf)2、Cu(MeCN)4PF6、Cu(MeCN)4BF4、CuTc、CuI、CuCl、Cu(OAc)2、CuBr2、CuCl2、Cu(acac)2Any one or more of them; most preferably, the copper catalyst is selected from CuBr.
According to the foregoing method of the invention, the nitrogen-containing or phosphorus-containing organic ligand is selected from one of the following:most preferably, the ligand is selected from
According to the method of the present invention, the photo-redox catalyst is [ Ir (dtbbpy) (ppy)2]PF6。
According to the method of the invention, the organic solvent is selected from any one or a mixture of several of 1, 4-dioxane, methanol, ethanol, acetonitrile, toluene, DMSO and DMF. Preferably, the organic solvent is selected from 1, 4-dioxane.
According to the method of the present invention, the inert atmosphere is an argon atmosphere or a nitrogen atmosphere, preferably an argon atmosphere.
The method according to the present invention, wherein the illumination is provided by a 5-24W blue LED, preferably an 18W blue LED. The reaction temperature is preferably 80-100 ℃, and most preferably 100 ℃; the reaction time is 4-48h, preferably 12-24h, most preferably 24 h.
According to the method of the present invention, the molar ratio of the nitrogen-containing nucleophile shown in formula 1, the diacyl peroxide shown in formula 2, the copper catalyst, the photo-oxidation-reduction catalyst, and the nitrogen-containing or phosphorus-containing organic ligand is 1 (1-3) (0.05-0.3) (0.005-0.1) (0.05-0.5); preferably, the molar ratio of the nitrogen-containing nucleophile of formula 1, the diacyl peroxide of formula 2, the copper catalyst, and the nitrogen-or phosphorus-containing organic ligand is 1:1.5:0.2:0.01: 0.3.
The method according to the present invention, wherein the post-processing operation is as follows:
concentrating the reaction solution to obtain a residue, and separating the residue by silica gel column chromatography to obtain the target product shown in formula 3, wherein the eluent of the silica gel column chromatography is a mixed solvent of petroleum ether/ethyl acetate.
Compared with the prior art, the method of the invention has the following beneficial effects:
the invention reports a free radical mediated decarboxylation C (sp) of diacyl peroxide and nitrogen-containing nucleophilic reagent for the first time3) -N cross-coupling reaction process. The method uses novel diacyl peroxide as an alkylation/acylation reagent, introduces different alkyl (secondary alkyl) or acyl (tertiary alkyl) into various nitrogen-containing nucleophiles under the common catalysis condition of copper catalysis and a photoredox catalyst, and has the advantages of mild and simple reaction condition, economy, cheapness, excellent yield and good adaptability of reaction substrates.
Detailed Description
The present invention will be described in more detail with reference to specific examples. Hereinafter, unless otherwise specified, the methods employed are conventional in the art, and the starting materials and reagents used may be obtained commercially and/or prepared by methods known in the art, for example, by using the corresponding alkylcarboxylic acid compounds, DMAP/DCC/H, for example, for the diacyl peroxides used in the present invention2O2Prepared by reaction under DCM (Angew. chem. int.Ed.2017,56,3650; chem. Sci.,2017,8, 2081; chem. Sci.2019,10,3632; J.Am.chem.Soc.2019,141, 548).
Example 1
To a Schlenk closed tube reactor, 1a indazole (0.2mmol), dicyclobutyryl peroxide of the formula 2m (2equiv,0.4mmol), CuBr (20 mol%, 0.04mmol), [ Ir (dtbbpy) (ppy)2]PF6(1mol%,0.002mmol),1,10-Phen(30mol percent, 0.06mmol) and 1, 4-dioxane (2mL), replacing the atmosphere in the reactor with argon, then placing the reactor under the irradiation of a 18W blue LED lamp, stirring the reaction at 100 ℃ until the raw materials are completely consumed through TLC and/or GC-MS monitoring, after the reaction is completed (24h), concentrating under reduced pressure to obtain a residue, and separating the residue through silica gel column chromatography (petroleum ether/ethyl acetate) to obtain the target product. Yellow oily liquid (25.8mg, 75% yield, R)f=0.9(PE/EA=20:1));1H NMR(500MHz,CDCl3)δ8.02(s,1H),7.71(d,J=8.5Hz,1H),7.43(d,J=8.5Hz,1H),7.34(m,1H),7.15-7.09(m,1H),5.10-5.03(m,1H),2.85-2.77(m,2H),2.52-2.47(m,2H),2.01-1.88(m,2H);13C NMR(126MHz,CDCl3)δ138.9,132.9,125.9,124.2,121.1,120.5,109.2,52.5,29.9,15.1;LRMS(EI,70eV)m/z(%):172(M+,13),144(100),118(38);HRMS m/z(ESI)calcd for C11H12N2([M+H]+)173.1073,found 173.1077。
Example 2
The alternative photocatalyst is Ir (ppy)3Otherwise, the reaction was not carried out under the same conditions as in example 1.
Example 3
The alternative photocatalyst is Ru (bpy)3Cl2·6H2O, otherwise, the reaction was not carried out under the same conditions as in example 1.
Example 4
The reaction was not carried out under the same conditions as in example 1 except that CzIPN was used as the photocatalyst.
Example 5
An alternative photocatalyst is [ Ir (dtbbpy) { dF (CF)3)ppy}2]PF6Otherwise, the reaction was not carried out under the same conditions as in example 1.
Example 6
The reaction was not allowed to proceed under the same conditions as in example 1 except that the reaction temperature was changed to room temperature.
Example 7
The reaction was carried out in a dark environment, but the reaction could not be carried out under the same conditions as in example 1.
Example 8
No photocatalyst [ Ir (dtbbpy) ((ppy))2]PF6Otherwise, the reaction was not carried out under the same conditions as in example 1.
Example 9
The same procedure as in example 1 was repeated except that the starting material was changed to a compound represented by 2n, to obtain the desired product represented by formula 3 an. Yellow oily liquid (24.5mg, 66% yield, R)f=0.9(PE/EA=20:1));1H NMR(500MHz,CDCl3)δ7.99(s,1H),7.72(d,J=8.0Hz,1H),7.46(d,J=8.5Hz,1H),7.35(t,J=7.5Hz,1H),7.13(t,J=7.5Hz,1H),5.03-4.97(m,1H),2.19-2.16(m,4H),2.00-1.95(m,2H),1.78-1.72(m,2H);13C NMR(126MHz,CDCl3)δ139.2,132.4,125.8,124.2,121.1,120.3,109.3,59.4,32.2,24.7;LRMS(EI,70eV)m/z(%):186(M+,31),131(33),118(100);HRMS m/z(ESI)calcd for C12H14N2([M+H]+)187.1230,found 187.1231。
Example 10
The same procedure as in example 1 was repeated except that the starting material was changed to a compound represented by 2o, to obtain the desired product represented by formula 3 ao. Yellow oily liquid (33.7mg, 56% yield, R)f=0.4(PE/EA=4:1));1H NMR(500MHz,CDCl3)δ8.00(s,1H),7.74(d,J=8.0Hz,1H),7.45(d,J=8.5Hz,1H),7.37(t,J=7.5Hz,1H),7.15(t,J=7.5Hz,1H),4.60-4.52(m,1H),4.31-4.25(m,2H),2.97(s,2H),2.24(d,J=10.0Hz,2H),2.02(d,J=12.0Hz,2H),1.49(s,9H);13C NMR(126MHz,CDCl3)δ154.6,138.7,133.0,126.1,124.2,121.3,120.6,108.8,79.8,56.1,43.5,31.5,28.5;LRMS(EI,70eV)m/z(%):301(M+,9),244(12),228(11),118(12);HRMS m/z(ESI)calcd for C17H23N3O2([M+H]+)302.1863,found 302.1862。
Example 11
The same procedure as in example 1 was repeated except that the starting material was a compound represented by 2p, to obtain the desired product represented by formula 3 ap. Yellow oily liquid (50.6mg, 96% yield, R)f=0.8(PE/EA=20:1));1H NMR(500MHz,CDCl3)δ8.44(d,J=8.5Hz,1H),7.67(s,1H),7.48(d,J=8.0Hz,1H),7.43(t,J=8.0Hz,1H),7.20-7.13(m,5H),7.07-7.03(m,1H),1.75(s,6H);13C NMR(126MHz,CDCl3)δ176.7,146.1,140.2,139.0,129.3,128.4,126.0,125.5,125.2,124.4,120.7,116.0,49.5,28.0;LRMS(EI,70eV)m/z(%):264(M+,15),119(57);HRMS m/z(ESI)calcd for C17H16N2O([M+H]+)265.1335,found265.1331。
Example 12
The same procedure as in example 1 was repeated except that the starting material was changed to a compound represented by 2q, to obtain the desired product represented by formula 3 aq. Yellow oily liquid (37.2mg, 86% yield, R)f=0.8(PE/EA=20:1));1H NMR(500MHz,CDCl3)δ8.40(d,J=8.5Hz,1H),8.00(s,1H),7.63(d,J=8.0Hz,1H),7.45(m,1H),7.27-7.22(m,1H),2.03(q,J=7.5Hz,2H),1.43(s,6H),0.75(t,J=7.5Hz,3H);13C NMR(126MHz,CDCl3)δ178.0,140.3,138.6,129.2,125.3,124.3,120.6,116.2,46.1,33.1,25.8,9.4;LRMS(EI,70eV)m/z(%):216(M+,17),118(100);HRMS m/z(ESI)calcd for C13H16N2O([M+H]+)217.1335,found217.1332。
Example 13
The same procedure as in example 1 was repeated except that the starting material was changed to a compound represented by 2r, to obtain the desired product represented by formula 3 ar. Yellow oily liquid (40.5mg, 65% yield, R)f=0.8(PE/EA=20:1));1H NMR(500MHz,CDCl3)δ8.45(d,J=8.5Hz,1H),8.09(s,1H),7.72(d,J=8.0Hz,1H),7.53(t,J=8.0Hz,1H),7.33(t,J=7.5Hz,1H),3.68(s,3H),2.31-2.26(m,6H),1.95-1.90(m,6H);13C NMR(126MHz,CDCl3)δ178.0,177.3,140.3,138.6,129.4,125.2,124.4,120.7,116.2,51.8,42.4,39.0,27.9,27.7;LRMS(EI,70eV)m/z(%):312(M+,100),253(19),118(36),108(10);HRMS m/z(ESI)calcd for C18H20N2O3([M+H]+)313.1547,found 313.1548。
Example 14
The same procedure as in example 1 was repeated except for substituting the starting material for the compound shown in 2s to obtain the desired product shown in formula 3 as. Yellow oily liquid (39.9mg, 57% yield, R)f=0.6(PE/EA=20:1));1H NMR(500MHz,CDCl3)δ8.48(d,J=8.5Hz,1H),8.05(s,1H),7.69(d,J=8.0Hz,1H),7.52(t,J=8.0Hz,1H),7.32(t,J=7.5Hz,1H),6.95(d,J=7.5Hz,1H),6.60(d,J=7.5Hz,1H),6.49(s,1H),3.85(t,J=6.0Hz,2H),2.31-2.26(m,2H),2.22(s,3H),2.12(s,3H),1.76-1.69(m,2H),1.57(d,J=1.0Hz,6H);13C NMR(126MHz,CDCl3)δ177.8,156.9,140.3,138.8,136.4,130.3,129.3,125.4,124.4,123.5,120.7,120.6,116.3,111.8,67.8,45.5,37.0,26.3,25.3,21.4,15.8;LRMS(EI,70eV)m/z(%):350(M+,16),229(52),205(36),118(70);HRMS m/z(ESI)calcd for C22H26N2O2([M+H]+)351.2067,found 351.2069。
Claims (13)
1. A photo-redox/copper co-catalyzed alkylation/acylation process comprising the steps of:
adding a nitrogen-containing nucleophilic reagent shown in a formula 1, a diacyl peroxide shown in a formula 2, a photooxidation-reduction catalyst, a copper catalyst, a nitrogen-containing or phosphorus-containing organic ligand and an organic solvent into a reactor, then replacing the atmosphere in the reactor with an inert atmosphere, placing the reactor under illumination and stirring at 60-120 ℃ for reaction, and after the reaction is completed, carrying out post-treatment to obtain a target product shown in a formula 3; the reaction formula is as follows:
in the above reaction formula, R1,R2Independently of one another, from hydrogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-20Cycloalkyl, substituted or unsubstituted C6-20Aryl, substituted or unsubstituted C2-20Heteroaryl, substituted or unsubstituted C6-20An arylsulfonyl group; or R1,R2Are connected to each other and to the connection R1,R2Together form C with or without other hetero atoms2-20The heterocyclic structure of (a), which is optionally substituted with a substituent; wherein R is1,R2Not simultaneously selected from hydrogen;
R3-R5independently of one another, from hydrogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-20Cycloalkyl, substituted or unsubstituted C6-20An aryl group; or R3、R4And/or R5Together forming a substituted or unsubstituted C with or without heteroatoms3-20A cyclic group;
the substituents in said "substituted or unsubstituted" and the substituents of said heterocyclic ring structure are selected from the group consisting of halogen, -CN, -NO2、C1-6Alkyl radical, C1-6Alkoxy, -CHO, phenyl, halophenyl, C1-6Alkyl-substituted phenyl, C1-6Alkoxy-substituted phenyl, 2-methylaminocarbonyl-4-pyridyloxy, C3-8Cycloalkyl radical, C2-12Alkynyl, C2-12Alkenyl, benzoyl, C1-6Alkoxycarbonyl group, C1-6Alkyl-substituted phenoxy;
and wherein: n is 0 or 1;
when n is 0, R3、R4、R5One of which is selected from hydrogen;
when n is 1, R3、R4、R5Are not hydrogen;
the copper catalyst is selected from CuBr, Cu (OTf)2、Cu(MeCN)4PF6、Cu(MeCN)4BF4、CuTc、CuI、CuCl、Cu(OAc)2、CuBr2、CuCl2、Cu(acac)2Any one or more of them;
the organic ligand containing nitrogen or phosphorus is selected from the following:
the photoredox catalyst is [ Ir (dtbbpy) (ppy)2]PF6。
2. The method of claim 1, wherein R1,R2Independently of one another, from hydrogen, methyl, substituted or unsubstituted phenyl, substituted or unsubstituted phenylsulfonyl; or R1,R2Are connected to each other and to the connection R1,R2Together form C with or without other hetero atoms2-12The heterocyclic structure of (a), which is optionally substituted with a substituent; wherein R is1,R2Is not simultaneously selected fromHydrogen;
R3-R5independently of one another, from hydrogen, methyl, ethyl, phenyl, substituted or unsubstituted propyl; or R3、R4And/or R5Together forming a substituted or unsubstituted C with or without heteroatoms3-8A cyclic group;
the substituents in said "substituted or unsubstituted" and the substituents of said heterocyclic ring structure are selected from the group consisting of halogen, -CN, -NO2、C1-6Alkyl radical, C1-6Alkoxy, -CHO, phenyl, halophenyl, C1-6Alkyl-substituted phenyl, C1-6Alkoxy-substituted phenyl, 2-methylaminocarbonyl-4-pyridyloxy, C3-8Cycloalkyl radical, C2-12Alkynyl, C2-12Alkenyl, benzoyl, C1-6Alkoxycarbonyl group, C1-6Alkyl-substituted phenoxy;
and wherein: n is 0 or 1;
when n is 0, R3、R4、R5One of which is selected from hydrogen;
when n is 1, R3、R4、R5Are not hydrogen.
5. The method according to any one of claims 1 to 3, wherein the organic solvent is selected from any one or more of 1, 4-dioxane, methanol, ethanol, acetonitrile, toluene, DMSO, and DMF.
6. The method of claim 5, wherein the organic solvent is selected from the group consisting of 1, 4-dioxane.
7. The method according to any one of claims 1 to 3, wherein the inert atmosphere is an argon atmosphere or a nitrogen atmosphere.
8. The method of claim 7, wherein the inert atmosphere is an argon atmosphere.
9. The method of any of claims 1-3, wherein the illumination is provided by a 5-24W blue LED; the reaction temperature is 80-100 ℃; the reaction time is 12-24 h.
10. The method of claim 9, wherein the illumination is provided by an 18W blue LED; the reaction temperature is 100 ℃; the reaction time was 24 h.
11. The method of any one of claims 1 to 3, wherein the molar ratio of the nitrogen-containing nucleophile of formula 1, the diacyl peroxide of formula 2, the copper catalyst, the photo-redox catalyst, and the nitrogen-or phosphorus-containing organic ligand is 1 (1-3): 0.05 to 0.3: (0.005 to 0.1): 0.05 to 0.5.
12. The method of claim 10, wherein the molar ratio of the nitrogen-containing nucleophile of formula 1, the diacyl peroxide of formula 2, the copper catalyst, the photo-redox catalyst, and the nitrogen-or phosphorus-containing organic ligand is 1:1.5:0.2:0.01: 0.3.
13. A method according to any one of claims 1-3, characterized in that the post-processing operation is as follows:
concentrating the reaction solution to obtain a residue, and separating the residue by silica gel column chromatography to obtain the target product shown in formula 3, wherein the eluent of the silica gel column chromatography is a mixed solvent of petroleum ether/ethyl acetate.
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