CN116462561A - Alkylation method of visible light-promoted alkenyl cycloalkane compound - Google Patents

Alkylation method of visible light-promoted alkenyl cycloalkane compound Download PDF

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CN116462561A
CN116462561A CN202310405356.2A CN202310405356A CN116462561A CN 116462561 A CN116462561 A CN 116462561A CN 202310405356 A CN202310405356 A CN 202310405356A CN 116462561 A CN116462561 A CN 116462561A
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刘宇
赵文杰
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Shenzhen Pengtai Biotechnology Co ltd
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Abstract

The invention discloses a method for alkylating alkenyl cycloalkane compound promoted by visible light, which takes alkenyl cycloalkane compound as raw material in Na 2 Under the Eosin Y photooxidation-reduction system, alkenyl cycloalkanes are used as alkyl radical acceptors to selectively obtain alkenyl transfer products, and the alkenyl transfer products have wide substrate universality and good target product yield.

Description

Alkylation method of visible light-promoted alkenyl cycloalkane compound
Technical Field
The application belongs to the technical field of organic synthesis methodologies, and particularly relates to a visible light-promoted alkylation method of alkenyl cycloalkane compounds.
Background
Carboxylic acid derivatives have great potential for use, for example, the simplest carboxylic acids (e.g., formic acid) are used not only in disinfectants, but also in textile treatments and reducing agents, and the like. Meanwhile, carboxylic acids are an important class of chemicals from which many other common chemicals, such as acid chlorides, anhydrides, esters, amides, etc., can be derived. These carboxylic acid derivatives have their own characteristics and find wide application in the chemical industry. Carboxylic acid derivatives are one of the most abundant, stable, and readily available decarboxylation alkylating or arylating reagents, widely used in transition metal catalyzed cross-coupling reactions. Despite significant advances in this area, there are problems such as the use of stoichiometric silver salt-promoted, highly toxic tin as a reducing agent or the need for an activator. Thus, there is an urgent need to develop a simpler, efficient and highly selective process that accomplishes this conversion under mild conditions.
The carboxylic acid derivative N- (acyloxy) phthalimide (NHPI ester) is a very important alkylating agent that has been widely used for radical-mediated decarboxylation transformations due to its ease of preparation, low cost, high stability and efficient formation of alkyl groups. NHPI esters are very electron accepting, generate a carbanionic radical intermediate via a Single Electron Transfer (SET) process, and are further efficiently decarboxylated to carbon-centered radicals under thermal, optical, and/or electrochemical conditions. In these ways, NHPI esters under single electron reduction, N-O bond cleavage and decarboxylation result in a series of alkyl intermediates for establishing C-C bonds, C-X bonds (x=n, O, S, si, B, etc.), and cascade cyclization reactions.
In recent years, since decarboxylation functionalization has advantages of mild reaction conditions, high selectivity and environmental friendliness under the promotion of visible light, research on NHPI esters as alkylating agents has been advanced significantly, and the inventors have conducted extensive and intensive studies on ring opening and cyclization reactions of alkenylcycloalkanes, and free radical decarboxylation functionalization reactions under the promotion of visible light (j. Org. Chem.2017,82,7394-7401; j.org.chem.2018,83,4657-4664; org.biomol.chem.2019,17,7918-7926; chem.Commun.2020,56,3011-3014; org.biomol.chem.2020,18,8677-8685; org.Lett.2022,24, 5726-5730). In the present invention, a method for the alkylation of alkenylcycloalkanes, promoted by visible light, was further developed by starting with alkenylcycloalkanes in Na 2 Under the Eosin Y photooxidation-reduction system, alkenyl cycloalkanes are used as alkyl radical acceptors to selectively obtain alkenyl transfer products, and the alkenyl transfer products have wide substrate universality and good target product yield.
Disclosure of Invention
The invention aims to enrich the existing synthesis strategy, and provides a novel visible light-promoted alkylation method of an alkenyl cycloalkane compound, an alkenyl cyclobutane substrate or an alkenyl cyclopentane substrate, and a preparation method of the alkenyl cycloalkane compound, wherein the alkenyl cyclobutane substrate or the alkenyl cyclopentane substrate is prepared by using Na 2 In the case of Eosin Y as a photoredox catalyst, the alkenyl-transferred product is selectively obtained as an alkyl acceptor, with a broad substrate universality and good target product yields.
The invention provides a method for alkylating alkenyl cycloalkane compounds promoted by visible light, which comprises the following steps:
adding an alkenyl cycloalkane compound shown in a formula 1, an NHPI ester compound shown in a formula 2 and Na into a reactor 2 The Eosin Y and an organic solvent, then the reactor is placed under the conditions of illumination and room temperature for stirring reaction, and the target product shown in the formula 3 is obtained after the reaction is completed and the post-treatment is carried out; the reaction formula is as follows:
in the method, in the process of the invention,represent C 6-20 Aryl, C 2-20 Heteroaryl; preferably, the +>Represents phenyl, naphthyl or thienyl;
R 1 represents substituents on the attached aromatic or heteroaromatic ring, R 1 The number being one or more, e.g. 1, 2, 3,4 or 5, each R 1 Independently of one another selected from hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Haloalkyl, benzyloxy. Preferably, R 1 Representation ofAre substituents of benzene rings, each R 1 Independently of each other, one or more selected from hydrogen, fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, benzyloxy.
n=1, 2 or 3, preferably 1 or 2.
R 2 Is substituted or unsubstituted C 1-10 Alkyl, C 4-20 Cycloalkyl, C 4-20 A heterocycloalkyl group; wherein said substituted or unsubstituted C 1-10 The substituents in the alkyl group are selected from phenyl, biphenyl, C 1-6 Alkylphenyl, halophenyl, phenoxy, C 1-6 Acyl, vinyl, C 1-6 One or more of haloalkyl groups.
Preferably, R 2 Is substituted or unsubstituted C 1-3 Alkyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, tetrahydrofuranyl, tetrahydropyranyl; wherein said substituted or unsubstituted C 1-3 The substituent in the alkyl is selected from one or more of phenyl, biphenyl, methylphenyl, chlorophenyl, bromophenyl, fluoro, phenoxy, acetyl, vinyl and trifluoromethyl.
Most preferably, the compound of formula 1 is selected from one of the following compounds:
the compound of formula 2 is selected from one of the following compounds:
according to the alkylation method, the organic solvent is selected from one or a combination of several solvents of DMF, acetonitrile, DMSO, methanol and ethanol, and the preferred organic solvent is DMF.
According to the alkylation process of the present invention, the illumination is provided by a 3-12W blue lamp, preferably a 5W blue lamp.
According to the alkylation method of the invention, the alkenyl cycloalkane compound shown in the formula 1, the NHPI ester compound shown in the formula 2 and Na 2 The molar ratio of the feed of Eosin Y is 1:1-5:0.01-0.1, preferably 1:2:0.02.
according to the alkylation process of the present invention, the reaction time of the stirred reaction is 8 to 48 hours, preferably 12 to 24 hours.
According to the aforementioned alkylation process of the present invention, the process is preferably carried out under a protective atmosphere, wherein the protective atmosphere is a nitrogen atmosphere or an argon atmosphere, preferably an argon atmosphere.
According to the alkylation method of the invention, the post-treatment is operated as follows: after the completion of the reaction, the reaction solution was washed with brine, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain a residue, which was separated by silica gel column chromatography to obtain the objective product.
Compared with the prior art, the method has the following advantages:
the invention is characterized in that Na 2 Under the condition of an Eosin Y/DMF photo-redox catalytic system, an alkenyl cyclobutane substrate or an alkenyl cyclopentane substrate is used as an alkyl acceptor, and an alkylated alkenyl transfer product is selectively obtained, but a ring-opening product is not obtained. Na (Na) 2 Eosin Y is cheaper than the common Ru and Ir photo-redox catalysts, and can provide significantly improved target product selectivity and yield.
The method of the invention has wide substrate universality, and NHPI ester can provide alkyl free radicals with different substitutions and steric hindrance under the reaction condition of the invention and obtain good target product yield.
Detailed Description
The present invention will be described in further detail with reference to specific examples. In the following, unless otherwise indicated, all procedures used are conventional in the art, reagents used are commercially available from conventional commercial sources in the art without further purification treatment, and/or are prepared via synthetic methods known in the art.
Example 1:
1-cyclobutyl-1-phenylethene (31.6 mg,0.2 mmol) of formula 1-1, NHPI ester compound (0.4 mmol,2 eq) of formula 2-1, na were successively added to a Schlenk tube reactor 2 Eosin Y (0.04 mmol,0.02 eq) and DMF (2 mL), the atmosphere in the reactor was replaced three times with argon, then the reactor was placed under 5W blue LED light and stirred at room temperature for 24 hours, the reaction was checked to be complete by TLC, the reaction solution was washed with brine (10 mL), extracted with ethyl acetate (3X 10 mL), the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to give a residue, which was separated by column chromatography over silica gel (eluting solvent: n-hexane/ethyl acetate, volume ratio 80:1) to give the target product of formula 5dg, yield 92%. 1 H NMR(400MHz,CDCl 3 ):δ7.30(t,J＝7.6Hz,2H),7.23-7.16(m,2H),3.90-3.86(m,2H),3.23(t,J＝11.6Hz,2H),2.80(t,J＝8.0Hz,4H),2.27(d,J＝6.8Hz,2H),1.55(d,J＝13.6Hz,2H),1.49-1.42(m,1H),1.28-1.18(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.0,139.3,128.8,128.0,127.2,125.9,68.0,37.7,33.7,33.0,31.8,31.0,17.0；HRMS(ESI-TOF)m/z:C 17 H 22 O(M+H) + calcd for 655.3662；found,655.3665。
Example 2:
the procedure of example 1 was followed except that the photocatalyst was replaced with tris (2, 2' -bipyridyl) ruthenium (II) chloride hexahydrate, to give a yield of 23%.
Example 3:
the procedure of example 1 was repeated except for replacing the photocatalyst with tris (2-phenylpyridine) iridium (III) and giving a yield of 31%.
Example 4:
the procedure of example 1 was followed except that the solvent was replaced with acetonitrile, to give a yield of 78%.
Example 5: reaction substrate universality test
Under the reaction conditions of example 1, the alkylated alkenyl transfer products of series 3 were prepared by substituting the reaction substrates of formulas 1 and 2, and the results are shown below:
structural characterization of the product:
compound 3ag: 1 H NMR(400MHz,CDCl 3 ):δ7.15(d,J＝8.8Hz,2H),6.85(d,J＝8.8Hz,2H),3.89-3.86(m,2H),3.80(s,3H),3.26-3.20(m,2H),2.79(t,J＝8.0Hz,4H),2.24(d,J＝6.8Hz,2H),2.00-1.92(m,2H),1.55(t,J＝13.2Hz,1H),1.28-1.18(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ157.7,137.9,132.4,128.2,113.4,55.1,37.7,33.7,33.0,31.7,31.0,17.0；HRMS(ESI-TOF)m/z:C 18 H 24 O 2 (M+H) + calcd for 272.1776；found,272.1778。
compound 3bg: 1 H NMR(400MHz,CDCl 3 ):δ7.43(d,J＝7.2Hz,2H),7.40-7.36(m,2H),7.34-7.32(m,1H),7.15(d,J＝8.4Hz,2H),6.92(d,J＝8.8Hz,2H),5.04(s,2H),3.89-3.86(m,2H),3.26-3.20(m,2H),2.79(t,J＝8.0Hz,4H),2.24(d,J＝7.2Hz,2H),2.00-1.89(m,2H),1.53(d,J＝13.2Hz,2H),1.49-1.44(m,1H),1.28-1.19(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ157.0,138.0,137.1,132.7,128.5,128.2(2C),128.0,127.5,114.3,70.0,68.0,37.7,33.7,33.0,31.8,31.0,17.0；HRMS(ESI-TOF)m/z:C 24 H 28 O 2 (M+H) + calcd for 348.2089；found,348.2092。
compound 3cg: 1 H NMR(400MHz,CDCl 3 ):δ7.11(s,4H),3.89-3.85(m,2H),3.26-3.20(m,2H),2.79(t,J＝8.0Hz,4H),2.33(s,3H),2.25(d,J＝7.2Hz,2H),2.00-1.91(m,2H),1.56-1.50(m,2H),1.47-1.42(m,1H),1.28-1.18(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ138.6,137.0,135.5,128.8,128.6,127.1,37.7,33.7,33.0,31.8,31.0,21.1,17.0；HRMS(ESI-TOF)m/z:C 17 H 22 O(M+H) + calcd for 256.1827；found,256.1832。
compound 3eg: 1 H NMR(400MHz,CDCl 3 ):δ7.19-7.15(m,2H),7.02-6.96(m,2H),3.90-3.86(m,2H),3.23(t,J＝11.2Hz,2H),2.80-2.74(m,4H),2.24(d,J＝6.8Hz,2H),1.53(d,J＝14.8Hz,2H),1.44-1.39(m,1H),1.26-1.17(m,2H)； 19 F NMR(282MHz,CDCl 3 ):δ-116.7(s,1F)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ161.1(d,J C-F ＝243.0Hz,1C),139.2,135.9(d,J C-F ＝3.2Hz,1C),128.7(d,J C-F ＝7.7Hz,1C),127.9,114.9(d,J C-F ＝21.0Hz,1C),68.0,37.9,33.7,32.9,31.6,30.9,16.9.；HRMS(ESI-TOF)m/z:C 17 H 21 FO(M+H) + calcd for 260.1576；found,260.1582。
compound 3fg: 1 H NMR(400MHz,CDCl 3 ):δ7.28-7.24(m,2H),7.14(d,J＝8.8Hz,2H),3.90-3.86(m,2H),3.26-3.20(m,2H),2.81-2.75(m,4H),2.24(d,J＝6.8Hz,2H),2.01-1.93(m,2H),1.53(t,J＝13.2Hz,2H),1.45-1.41(m,1H),1.27-1.17(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.1,138.4,131.5,128.5,128.2,127.9,67.9,37.7,33.7,32.9,31.7,31.0,16.9；HRMS(ESI-TOF)m/z:C 17 H 21 ClO(M+H) + calcd for 276.1281；found,276.1283。
compound 3hg: 1 H NMR(400MHz,CDCl 3 ):δ7.42(d,J＝8.4Hz,2H),7.08(d,J＝8.0Hz,2H),3.90-3.86(m,2H),3.23(t,J＝10.4Hz,2H),2.80-2.75(m,4H),2.24(d,J＝6.8Hz,2H),2.01-1.93(m,2H),1.51(d,J＝13.2Hz,2H),1.44-1.38(m,1H),1.27-1.17(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.2,138.9,131.2,128.9,127.9,119.6,67.9,37.6,33.7,32.9,31.7,31.0,16.9；HRMS(ESI-TOF)m/z:C 17 H 21 BrO(M+H) + calcd for 320.0776；found,320.0779。
compound 3ig: 1 H NMR(400MHz,CDCl 3 ):δ7.55(d,J＝8.0Hz,2H),7.31(d,J＝8.0Hz,2H),3.90-3.87(m,2H),3.26-3.20(m,2H),2.84-2.78(m,4H),2.29(d,J＝7.2Hz,2H),2.03-1.95(m,2H),1.53(d,J＝13.2Hz,2H),1.47-1.38(m,1H),1.28-1.18(m,2H)； 19 F NMR(282MHz,CDCl 3 ):δ-62.3(s,3F)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ143.8,141.8,128.0(q,J C-F ＝10.0Hz,1C),125.7,125.0(q,J C-F ＝3.8Hz,1C),123.0,120.3,67.9,37.6,33.8,32.9,31.8,31.1,17.0.；HRMS(ESI-TOF)m/z:C 18 H 21 F 3 O(M+H) + calcd for 310.1544；found,310.1549。
compound 3jg: 1 H NMR(400MHz,CDCl 3 ):δ7.22(t,J＝7.6Hz,1H),6.82(d,J＝8.0Hz,1H),6.77-6.73(m,2H),3.90-3.86(m,2H),3.80(s,3H),3.27-3.20(m,2H),2.83-2.78(m,4H),2.25(d,J＝6.8Hz,2H),2.00-1.92(m,2H),1.57-1.50(m,2H),1.53-1.43(m,1H),1.28-1.18(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ159.3,141.5,139.5,128.9,128.8,119.8,113.3,110.9,68.0,55.1,37.7,33.7,33.0,31.8,31.0,17.0；HRMS(ESI-TOF)m/z:C 18 H 24 O 2 (M+H) + calcd for 272.1776；found,272.1773。
compound 3kg: 1 H NMR(400MHz,CDCl 3 ):δ7.22-7.18(m,1H),7.04-7.02(m,1H),6.90-6.86(m,2H),3.90-3.86(m,2H),3.80(s,3H),3.27-3.20(m,2H),2.78(t,J＝6.8Hz,2H),2.54-2.51(m,2H),2.23(d,J＝6.8Hz,2H),1.96-1.88(m,2H),1.57(d,J＝13.2Hz,2H),1.36-1.29(m,1H),1.26-1.19(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ156.9,139.1,130.6,129.3,127.7,127.5,120.2,110.8,68.1,55.3,38.5,33.8,33.1,30.3,30.1,16.3；HRMS(ESI-TOF)m/z:C 18 H 24 O 2 (M+H) + calcd for272.1776；found,272.1774。
compound 3lg: 1 H NMR(400MHz,CDCl 3 ):δ6.80(d,J＝8.8Hz,1H),6.75-6.71(m,1H),6.62(d,J＝3.2Hz,1H),3.90-3.86(m,2H),3.76(d,J＝3.6Hz,6H),3.24(t,J＝11.2Hz,2H),2.77(t,J＝7.6Hz,2H),2.55(t,J＝7.6Hz,2H),6.8(d,J＝6.8Hz,2H),1.96-1.88(m,2H),1.57(d,J＝12.8Hz,2H),1.37-1.30(m,1H),1.25-1.16(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ153.1,151.3,139.4,130.5,127.6,117.0,111.9,111.4,68.1,56.0,55.6,38.5,33.8,33.1,30.4,30.1,16.3；HRMS(ESI-TOF)m/z:C 19 H 26 O 3 (M+H) + calcd for 302.1882；found,302.1885。
compound 3mg: 1 H NMR(400MHz,CDCl 3 ):δ7.18(d,J＝4.8Hz,1H),7.01-6.99(m,1H),6.87(d,J＝3.2Hz,1H),3.94-3.90(m,2H),3.33-3.27(m,2H),2.97(t,J＝8.4Hz,2H),2.86-2.82(m,2H),2.28(d,J＝7.2Hz,2H),2.08-2.01(m,2H),1.80-1.72(m,1H),1.64(t,J＝11.6Hz,2H),1.35-1.25(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ143.8,140.1,126.6,123.3,122.6,68.1,38.2,34.5,33.2,32.6,31.0,16.7；HRMS(ESI-TOF)m/z:C 15 H 20 OS(M+H) + calcd for 248.1235；found,248.1238。
compound 3ng: 1 H NMR(400MHz,CDCl 3 ):δ7.81-7.76(m,3H),7.64(s,1H),7.48-7.38(m,3H),3.89-3.85(m,2H),3.23-3.17(m,2H),2.86(t,J＝7.6Hz,4H),2.32(d,J＝6.8Hz,2H),2.03-1.93(m,2H),1.57-1.55(m,2H),1.51-1.45(m,1H),1.31-1.21(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.0,137.7,133.4,132.0,129.0,127.8,127.5,126.0,125.9,125.7,125.4,68.0,37.8,33.8,33.0,31.8,31.1,17.0；HRMS(ESI-TOF)m/z:C 21 H 24 O(M+H) + calcd for 292.1827；found,292.1831。
compound 3da: 1 H NMR(400MHz,CDCl 3 ):δ7.31-7.20(m,6H),7.18-7.11(m,4H),2.80(t,J＝8.0Hz,4H),2.54(t,J＝7.6Hz,2H),2.35(t,J＝7.6Hz,2H),1.62-1.55(m,2H),1.40-1.33(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ142.8,140.0,138.0,130.8,128.3,128.2,128.0,127.2,125.8,125.5,35.7,31.8,31.1,30.7,30.3,27.9,17.0；HRMS(ESI-TOF)m/z:C 21 H 24 (M+H) + calcd for 276.1878；found,276.1875.。
compound 3db: 1 H NMR(400MHz,CDCl 3 ):δ7.32-7.27(m,2H),7.21-7.15(m,3H),7.06-7.03(m,2H),6.93-6.89(t,J＝8.8Hz,2H),2.82-2.74(m,4H),2.53(t,J＝7.6Hz,2H),2.00-1.92(m,2H),1.65-1.60(m,2H)； 19 F NMR(282MHz,CDCl 3 ):δ-118.2(s,1F)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ161.1(d,J C-F ＝241.4Hz,1C),139.8,138.4,138.1(d,J C-F ＝3.1Hz,1C),130.5,129.6(d,J C-F ＝7.7Hz,1C),128.0,127.2,125.9,114.8(d,J C-F ＝20.9Hz,1C),34.6,31.8,30.7,30.0,29.9,17.0.；HRMS(ESI-TOF)m/z:C 20 H 21 F(M+H) + calcd for 280.1627；found,280.1634。
compound 3dd: 1 H NMR(400MHz,CDCl 3 ):δ7.39-7.35(m,3H),7.32(d,J＝7.2Hz,1H),7.25-7.24(m,2H),7.22-7.18(m,1H),6.98(d,J＝8.4Hz,2H),2.77(t,J＝8.0Hz,2H),2.63-2.52(m,6H),1.95-1.87(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ141.3,139.5,139.3,131.4,131.1,130.3,130.2,129.4,128.2,127.2,126.0,119.4,34.0,32.5,31.8,30.6,16.9；HRMS(ESI-TOF)m/z:C 19 H 19 Br(M+H) + calcd for326.0670；found,326.0673。
compound 3de: 1 H NMR(400MHz,CDCl 3 ):δ7.50(d,J＝8.0Hz,2H),7.36-7.32(m,2H),7.25-7.21(m,5H),2.77(t,J＝6.8Hz,2H),2.67-2.59(m,6H),1.95-1.87(m,2H)； 19 F NMR(282MHz,CDCl 3 ):δ-62.2(s,3F)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ146.4,139.4,128.2(q,J C-F ＝11.8Hz,1C),127.3(q,J C-F ＝10.0Hz,1C),126.4,126.1,125.8,125.1(q,J C-F ＝11.4Hz,1C),123.1,120.4,34.5,32.4,31.8,30.6,16.9.；HRMS(ESI-TOF)m/z:C 20 H 19 F 3 (M+H) + calcd for 316.1439；found,316.1442。
compound 3df: 1 H NMR(400MHz,CDCl 3 )δ:7.34(t,J＝7.6Hz,2H),7.27(s,1H),7.23-7.15(m,4H),7.12(s,1H),7.03-6.98(m,1H),2.78(t,J＝7.6Hz,2H),2.65-2.55(m,6H),1.96-1.88(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ144.3,139.5,139.4,133.8,129.6,129.3,128.6,128.2,127.2,126.7,126.6,126.3,126.0,125.8,34.3,32.4,31.8,30.6,16.9；HRMS(ESI-TOF)m/z:C 19 H 19 Cl(M+H) + calcd for 282.1175,found 282.1178。
compound 3dh: 1 H NMR(400MHz,CDCl 3 ):δ7.32-7.29(m,2H),7.24-7.21(m,2H),7.19-7.14(m,1H),2.79(t,J＝8.0Hz,4H),2.20(d,J＝6.8Hz,2H),1.99-1.91(m,2H),1.74-1.57(m,5H),1.22-1.18(m,1H),1.09(s,3H),0.89-0.83(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.4,138.5,129.9,127.9,127.3,125.7,38.3,36.4,33.3,31.8,31.1,26.6,26.2,17.0；HRMS(ESI-TOF)m/z:C 18 H 24 (M+H) + calcd for240.1878；found,240.1875。
compound 3di: 1 H NMR(400MHz,CDCl 3 ):δ7.26(t,J＝7.2Hz,2H),7.20(d,J＝7.6Hz,2H),7.13(t,J＝7.2Hz,1H),2.79-2.70(m,4H),2.26(s,2H),1.95-1.87(m,2H),1.17-1.11(m,2H),0.73(t,J＝7.6Hz,1H),0.67(s,3H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ142.4,140.2,130.1,127.7,127.5,125.5,42.2,35.8,35.1,32.0,31.7,26.8,17.1,8.5；HRMS(ESI-TOF)m/z:C 16 H 20 (M+H) + calcd for 212.1565；found,212.1568。
compound 3dj: 1 H NMR(400MHz,CDCl 3 ):δ7.25(t,J＝4.4Hz,2H),7.22(t,J＝6.8Hz,2H),7.15-7.12(m,1H),2.79-2.75(m,4H),2.15(s,2H),2.00-1.88(m,2H),1.83(s,3H),1.61-1.47(m,7H),1.34(d,J＝2Hz,6H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.1,139.1,137.8,134.1,31.9,30.7,30.6,30.3,22.5,17.0,13.9；HRMS(ESI-TOF)m/z:C 22 H 28 (M+H) + calcd for 292.2191；found,292.2196。
compound 3dk: 1 H NMR(400MHz,CDCl 3 ):δ7.31-7.27(m,2H),7.24-7.20(m,2H),7.19-7.14(m,1H),7.07(t,J＝8.0Hz,2H),7.02(d,J＝8.0Hz,2H),2.80(d,J＝8.0Hz,4H),2.50(t,J＝8.0Hz,2H),2.35(t,J＝7.6Hz,2H),2.30(s,3H),2.00-1.92(m,2H),1.60-1.52(m,2H),1.40-1.32(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.0,139.7,138.0,134.9,130.8,128.9,128.2,128.0,127.2,125.8,35.3,31.8,31.2,30.7,30.3,27.9,21.0,17.0；HRMS(ESI-TOF)m/z:C 22 H 26 (M+H) + calcd for290.2035；found,290.2037。
compound 3dl: 1 H NMR(400MHz,CDCl 3 ):δ7.36-7.34(m,2H),7.31-7.27(m,2H),7.21-7.15(m,3H),6.98(d,J＝8.4Hz,2H),2.79(t,J＝7.6Hz,4H),2.49(t,J＝8.0Hz,2H),2.34(t,J＝7.6Hz,2H),2.00-1.92(m,2H),1.61-1.51(m,2H),1.37-1.30(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ141.7,139.9,138.1,131.2,130.7,130.1,128.0,127.2,125.8,119.2,35.1,31.8,30.8,30.7,30.2,27.7,17.0；HRMS(ESI-TOF)m/z:C 21 H 23 Br(M+H) + calcd for 354.0983；found,354.0988。
compound 3dm: 1 H NMR(400MHz,CDCl 3 ):δ7.29(t,J＝7.2Hz,2H),7.23(d,J＝7.6Hz,2H),7.18-7.14(m,1H),2.81(t,J＝8.0Hz,4H),2.32(t,J＝6.4Hz,2H),2.00-1.93(m,2H),1.30-1.26(m,4H),0.86-0.83(m,3H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.1,137.8,127.9,127.2,126.4,125.7,31.9,30.7,30.6,30.3,22.5,17.0,13.9；HRMS(ESI-TOF)m/z:C 15 H 20 (M+H) + calcd for 200.1565；found,200.1568。
compound 3dn: 1 H NMR(400MHz,CDCl 3 ):δ7.32-7.28(m,4H),7.25-7.16(m,3H),6.94-6.87(m,1H),6.83-6.79(m,2H),3.90(t,J＝7.6Hz,2H),2.88-2.82(m,6H),2.03-1.95(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ158.8,141.1,139.4,129.3,128.2,127.1,126.5,126.1,120.5,114.5,66.4,32.0,30.9,30.8,17.0；HRMS(ESI-TOF)m/z:C 20 H 22 O(M+H) + calcd for 278.1671；found,278.1674。
compound 3do: 1 H NMR(400MHz,CDCl 3 ):δ7.29(t,J＝7.2Hz,2H),7.22(t,J＝6.8Hz,2H),7.18-7.14(m,1H),2.80(t,J＝7.6Hz,4H),2.37-2.32(m,4H),2.08(s,3H),2.01-1.93(m,2H),1.58-1.50(m,2H),1.34-1.26(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ209.3,139.8,138.3,130.5,128.0,127.2,125.8,43.6,31.8,30.7,30.2,29.8,27.8,23.5,17.0；HRMS(ESI-TOF)m/z:C 17 H 22 O(M+H) + calcd for 242.1671；found,242.1674。
compound 3dp: 1 H NMR(400MHz,CDCl 3 )δ:7.34(d,J＝8.4Hz,2H),7.31-7.27(m,2H),7.20-7.15(m,3H),6.97(d,J＝8.4Hz,2H),2.81-2.74(m,4H),2.51(t,J＝8.0Hz,2H),2.35(t,J＝7.2Hz,2H),2.00-1.92(m,2H),1.64-1.57(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ141.5,140.0,138.4,131.2,130.1,128.0,127.2,125.9,119.2,34.8,31.8,30.7,30.0,29.7,17.0；HRMS(ESI-TOF)m/z:C 20 H 21 Br(M+H) + calcd for 340.0827；found,340.0825。
compound 3dq: 1 H NMR(400MHz,CDCl 3 ):δ7.29(t,J＝7.2Hz,2H),7.24(d,J＝7.2Hz,2H),7.17(t,J＝7.2Hz,1H),5.82-5.72(m,1H),4.99-4.90(m,2H),2.81(t,J＝8.0Hz,4H),2.34(t,J＝7.6Hz,2H),2.04-1.95(m,4H),1.44-1.37(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.0,138.9,138.2,130.7,128.0,127.2,125.8,114.3,33.4,31.9,30.7,30.0,27.6,17.0；HRMS(ESI-TOF)m/z:C 16 H 20 (M+H) + calcd for 212.1565；found,212.1563。
compound 3dr: 1 H NMR(400MHz,CDCl 3 ):δ7.33(t,J＝7.2Hz,1H),7.24-7.21(m,4H),7.05-7.03(m,4H),2.77(t,J＝7.2Hz,2H),2.63-2.55(m,6H),1.95-1.87(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ140.8,139.6,139.4,139.3,129.9,129.8,128.4,128.2,127.3,126.0,37.0,33.9,31.8,30.6,16.9；HRMS(ESI-TOF)m/z:C 19 H 19 Cl(M+H) + calcd for 282.1175；found,282.1177.。
compound 3ds: 1 H NMR(400MHz,CDCl 3 ):δ7.72(d,J＝7.2Hz,2H),7.58(d,J＝7.6Hz,1H),7.51(t,J＝7.6Hz,1H),7.38(t,J＝7.6Hz,2H),7.31(t,J＝6.8Hz,1H),7.20-7.15(m,2H),7.07-7.04(m,1H),6.97(d,J＝1.6Hz,1H),6.90(d,J＝8.4Hz,1H),3.48(s,3H),3.09(d,J＝14.8Hz,1H),2.98-2.90(m,1H),2.77-2.70(m,2H),2.65-2.57(m,2H),2.30-2.23(m,1H),1.31(s,3H),1.12-1.09(m,6H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ141.6,141.2,139.7,139.1,138.6,129.8,128.9,128.7,128.1,127.3,127.0,126.9,126.0,34.4,32.7,31.8,30.6,17.0；HRMS(ESI-TOF)m/z:C 25 H 24 (M+H) + calcd for 324.1878；found,324.1876。
compound 3dt: 1 H NMR(400MHz,CDCl 3 ):δ7.36-7.31(m,5H),7.22-7.17(m,1H),7.16-7.10(m,3H),2.81(t,J＝7.6Hz,2H),2.75-2.61(m,6H),1.96-1.89(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ139.8,139.6(2C),133.9,130.7,129.5,129.3,128.1,127.2,126.5,126.0,32.8,31.9,30.8,30.7,17.0；HRMS(ESI-TOF)m/z:C 19 H 19 Cl(M+H) + calcd for 282.1175；found,282.1177。
compound 3oa: 1 H NMR(400MHz,CDCl 3 ):δ7.30-7.22(m,4H),7.19-7.10(m,6H),2.53(t,J＝8.0Hz,2H),2.41-2.34(m,4H),2.11(t,J＝7.2Hz,2H),1.72-1.66(m,2H),1.60-1.51(m,4H),1.37-1.30(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ143.8,142.8,140.0,131.8,128.3(2C),128.2,127.8,126.1,125.7,125.5,124.7,35.8,34.7,32.4,31.3,30.6,27.7,26.9,26.4；HRMS(ESI-TOF)m/z:C 22 H 26 (M+H) + calcd for 290.2035；found,290.2038。
compound 3og: 1 H NMR(400MHz,CDCl 3 ):δ7.30(t,J＝7.6Hz,2H),7.21-7.14(m,3H),3.90-3.86(m,2H),3.26-3.21(m,2H),2.38-2.32(m,4H),2.14(t,J＝7.2Hz,2H),1.73-1.66(m,2H),1.59-1.54(m,4H),1.43-1.37(m,1H),1.28-1.23(m,2H)； 13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ143.8,141.6,129.7,128.3,127.9,125.8,68.0,42.2,33.8,33.1,32.4,31.0,26.8,26.4；HRMS(ESI-TOF)m/z:C 18 H 24 O(M+H) + calcd for256.1827；found,256.1829。
the above-described embodiments are merely preferred embodiments of the present invention and are not intended to be exhaustive of the possible implementations of the present invention. Any obvious modifications thereof, without departing from the principles and spirit of the present invention, should be considered to be within the scope of the appended claims.

Claims (9)

1. A method for the visible light-promoted alkylation of an alkenylcycloalkane compound, comprising the steps of:
adding an alkenyl cycloalkane compound shown in a formula 1, an NHPI ester compound shown in a formula 2 and Na into a reactor 2 The Eosin Y and an organic solvent, then the reactor is placed under the conditions of illumination and room temperature for stirring reaction, and after the reaction is completed, the target product shown in the formula 3 is obtained through post-treatment; the reaction formula is as follows:
in the method, in the process of the invention,represent C 6-20 Aryl, C 2-20 Heteroaryl;
R 1 represents substituents on the attached aromatic or heteroaromatic ring, each R 1 Independently of one another selected from hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 One or more of haloalkyl and benzyloxy;
n=1, 2 or 3;
R 2 is substituted or unsubstituted C 1-10 Alkyl, C 4-20 Cycloalkyl, C 4-20 A heterocycloalkyl group; wherein said substituted or unsubstituted C 1-10 The substituents in the alkyl group are selected from phenyl, biphenyl, C 1-6 Alkylphenyl, halophenyl, phenoxy, C 1-6 Acyl, vinyl, C 1-6 One or more of haloalkyl groups.
2. The method for the alkylation of alkenylcycloalkanes under visible light acceleration according to claim 1,represents phenyl, naphthyl or thienyl;
R 1 representation ofAre substituents of benzene rings, each R 1 Independently of each other, one or more selected from hydrogen, fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, benzyloxy;
n=1 or 2;
R 2 is substituted or unsubstituted C 1-3 Alkyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, tetrahydrofuranyl, tetrahydropyranyl; wherein said substituted or unsubstituted C 1-3 The substituent in the alkyl is selected from one or more of phenyl, biphenyl, methylphenyl, chlorophenyl, bromophenyl, fluoro, phenoxy, acetyl, vinyl and trifluoromethyl.
3. The method for the visible light-promoted alkylation of alkenylcycloalkanes according to claim 1, wherein the compound of formula 1 is selected from one of the following compounds:
the compound of formula 2 is selected from one of the following compounds:
4. the method for alkylating an alkenylcycloalkane compound according to claim 1, wherein the organic solvent is selected from one or more solvents selected from DMF, acetonitrile, DMSO, methanol, ethanol.
5. The alkylation process of claim 1, wherein the illumination is provided by a 3-12W blue light lamp.
6. The method for the alkylation of alkenylcycloalkane compound according to claim 1, wherein the alkenylcycloalkane compound represented by formula 1, the NHPI ester compound represented by formula 2 and Na 2 The molar ratio of the feed of Eosin Y is 1:1-5:0.01-0.1.
7. The method for the visible light-promoted alkylation of alkenylcycloalkanes according to claim 1, wherein the reaction time of the stirring reaction is 8 to 48 hours.
8. The method for the alkylation of alkenylcycloalkanes promoted with visible light according to claim 1 or 2, wherein the reaction is carried out under a protective atmosphere of nitrogen or argon.
9. The method for the alkylation of alkenylcycloalkanes, promoted by visible light, according to claim 1 or 2, characterized in that said post-treatment is carried out as follows: after the completion of the reaction, the reaction solution was washed with brine, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain a residue, which was separated by silica gel column chromatography to obtain the objective product.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013144224A1 (en) * 2012-03-27 2013-10-03 Syngenta Participations Ag Acetylenic microbiocides
CN108707081A (en) * 2018-07-09 2018-10-26 南昌航空大学 A kind of alkene 1,2- difunctionalities dough reaction method
US20210206702A1 (en) * 2020-01-02 2021-07-08 National Tsing Hua University Method for oxidative cleavage of compounds with unsaturated double bond
CN115232066A (en) * 2022-07-08 2022-10-25 江西师范大学 Method for synthesizing 1, 2-alkyl aryl ethane compound by photocatalysis of olefin

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013144224A1 (en) * 2012-03-27 2013-10-03 Syngenta Participations Ag Acetylenic microbiocides
CN108707081A (en) * 2018-07-09 2018-10-26 南昌航空大学 A kind of alkene 1,2- difunctionalities dough reaction method
US20210206702A1 (en) * 2020-01-02 2021-07-08 National Tsing Hua University Method for oxidative cleavage of compounds with unsaturated double bond
CN115232066A (en) * 2022-07-08 2022-10-25 江西师范大学 Method for synthesizing 1, 2-alkyl aryl ethane compound by photocatalysis of olefin

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