A method for synthesizing a furan compound

Abstract

The present invention relates to the technical field of organic synthesis, and particularly relates to a method for synthesizing furan compounds. Mix α,β-unsaturated ketone A, acylsilane B and an organic solvent, stir and react the mixed solution under the conditions of light and 0-30 °C, and then separate and purify to obtain the furan compound. The synthesis method of the present invention directly synthesizes furan compounds by a one-step method, which is a new reaction mode, provides a simple and efficient method for synthesizing polysubstituted furans, has simple, efficient and mild reaction conditions, does not require the addition of additional catalysts, has good functional group tolerance and substrate generality, can be compatible with various functional groups such as ester groups, halogens, carbonyl groups, and various linear or branched alkyl groups can also complete this reaction.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, and particularly relates to a method for synthesizing furan compounds. Background Art

[0002] Due to the special structure of acylsilanes in which both the oxygen atom and the silicon atom are connected to the same sp 2 carbon atom, they have many unique chemical and physical properties and are extremely important organic synthesis intermediates. [C.Bolm, Acylsilanes: valuable organosilicon reagents in organic synthesis, Chem.Soc.Rev, 2013, 42, 8540] Furan, as a class of compounds widely present in natural products, functional materials and drugs, its synthesis is also a very important research direction. [X.-L.Hou, Five-Membered Ring Systems: Furans and Benzofurans, Prog.Heterocycl.Chem.2011, 22, 181] Currently, the reported reactions of acylsilanes with α,β-unsaturated ketones have all obtained 1,4-diketone compounds under the catalysis of transition metals or organic small molecules. [a) J.Am.Chem.Soc.2004, 126, 2314-2315. b) ACS Catal.2018, 8, 304-309.] There is no report on the direct one-step method for synthesizing furan from acylsilanes and α,β-unsaturated ketones. Summary of the Invention

[0003] The purpose of the present invention is to provide a method for synthesizing furan compounds. Through a simple cyclization reaction of α,β-unsaturated ketones and acylsilanes under light, furan compounds can be directly synthesized in one step, which can be applied to the synthesis of various substituted furans without the need to add additional catalysts. The reaction conditions are simple, mild and efficient, and have good substrate generality and functional group tolerance.

[0004] The solution adopted by the present invention to achieve the purpose is: a method for synthesizing furan compounds, mixing α,β-unsaturated ketone A, acylsilane B and an organic solvent, stirring and reacting the mixed solution under the conditions of light and 0-30 °C, and then separating and purifying to obtain the furan compound.

[0005] Preferably, the molecular structural formula of the furan compound is as follows:

[0006]

[0007] The molecular structural formula of the α,β-unsaturated ketone A is

[0008] The molecular structural formula of the acylsilane B is as follows:

[0009] Among them, R 1 , R 2 are each independently any one of aryl, heteroaryl, alkyl, alkenyl, alkynyl, ester group, carboxyl group, sulfonyl group, heteroatom, and hydrogen atom, and may be the same or different; R 3 is any one of aryl, heteroaryl, alkyl, alkenyl, alkynyl, ester group, sulfonyl group, heteroatom, and hydrogen atom; R 4 , R 5 , R 6 are each independently any one of aryl, heteroaryl, alkyl, alkenyl, alkynyl, ester group, sulfonyl group, heteroatom, and hydrogen atom, and may be the same or different.

[0010] In the present invention, the types of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 in the α,β-unsaturated ketone A and the acylsilane B used do not affect the occurrence of the cyclization reaction, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 can be selected from any kind of group.

[0011] Preferably, the alkyl group has 1 - 20 carbon atoms and is a straight-chain structure, cyclic structure, or branched-chain structure; the alkyl group has one or more substituents, and when there are multiple substituents, the substituents may be the same or different, and the positions may be the same or different.

[0012] Preferably, the aryl group has one or more substituents; when there are multiple substituents, the substituents may be the same or different.

[0013] Preferably, the organic solvent is at least one of methanol, ethanol, isopropanol, tert-butanol, tetrahydrofuran, 2-methyltetrahydrofuran, diethyl ether, dimethylethyl ether, methyl tert-butyl ether, 1,4-epoxyhexane, 1,3-epoxyhexane, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, saturated alkane of C 4-12 , fluorinated or chlorinated alkane of C 3-12 , benzene, toluene, xylene, trimethylbenzene, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, acetone, N-methylpyrrolidone, acetonitrile, saturated alkyl nitrile of C 3-12 .

[0014] Preferably, the molar ratio between the α,β-unsaturated ketone A and the acylsilane B is 1-6:1; the concentration of the acylsilane B in the mixed solution is between 0.1M and 1M.

[0015] Preferably, the light source for the illumination is any one of white light, blue light, purple light, green light, and sunlight, and the power of the light source is between 1W and 60W.

[0016] Preferably, the separation and purification include filtration, concentration, recrystallization, and column chromatography.

[0017] The present invention has the following advantages and beneficial effects: (1) The synthesis method of the present invention realizes the cyclization reaction of the α,β-unsaturated ketone A and the acylsilane B, and directly synthesizes furan compounds by a one-step method, which is a new reaction mode and provides a simple and efficient method for synthesizing polysubstituted furans.

[0018] (2) The synthesis method of the present invention has simple, efficient, and mild reaction conditions and does not require the addition of extra catalysts.

[0019] (3) The reaction conditions involved in the synthesis method of the present invention have good functional group tolerance and substrate generality, can be compatible with various functional groups such as ester groups, halogens, and carbonyl groups, and various straight-chain or branched alkyl groups can also complete this reaction. Specific Embodiments

[0020] To better understand the present invention, the following examples further illustrate the present invention, but the content of the present invention is not limited to the following examples.

[0021] Example 1:

[0022]

[0023] Add A (172.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry DCM (2 mL) to a dry photoreaction tube equipped with a magnetic stir bar. Seal the photoreaction tube and then irradiate it with a 6W green LED lamp. The reaction mixture is stirred at room temperature for 24 hours. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (20 / 1-10 / 1, v / v) to obtain the target compound G1 (63.3 mg of colorless oily liquid, yield 73%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.73–7.70 (m, 2H), 7.58–7.53 (m, 3H), 7.43–7.29 (m, 10H), 6.49 (s, 1H), 4.36 (s, 2H), 0.55 (s, 6H).13 13C NMR (151 MHz, CDCl3, 25 °C) δ 157.9, 157.8, 138.1, 136.6, 134.0, 133.9, 130.1, 129.7, 129.0, 128.7, 128.7, 128.6, 128.1, 126.8, 125.1, 108.4, 54.2, –2.9. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.3. IR (ATR): 2960, 2922, 1744, 1588, 1480, 1320, 1148, 1088, 835, 738, 701 cm -1 . HRMS (ESI + , m / z): calcd for C 25 H 25 O3SSi + (M + H) + : 433.1288; Found: 433.1283.

[0024] Example 2:

[0025]

[0026] To a dry photoreaction tube equipped with a magnetic stir bar, add A (180.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry 1,2-dichloroethane (2 mL). Seal the photoreaction tube and then irradiate with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G2 (56.0 mg of colorless oily liquid, yield 63%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.74–7.70 (m, 2H), 7.58–7.53 (m, 3H), 7.42–7.37 (m, 5H), 7.30–7.26 (m, 2H), 7.17–7.12 (m, 2H), 6.47 (s, 1H), 4.34 (s, 2H), 2.36 (s, 3H), 0.54 (s, 6H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 158.1, 157.5, 138.6, 138.2, 136.7, 134.0, 133.9, 129.6, 129.4, 129.0, 128.8, 128.0, 127.3, 126.7, 125.0, 107.9, 54.3, 21.4, –2.9. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.4. IR (ATR): 3068, 2960, 2922, 1487, 1446, 1320, 1148, 1085, 813, 783, 738, 701 cm -1 . HRMS (ESI + , m / z): C 26 H 27 O3SSi + (M + H) +: 447.1445; Found: 447.1428.

[0027] Example 3:

[0028]

[0029] To a dry photoreaction tube equipped with a magnetic stir bar, add A (182.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry toluene (0.5 mL). Seal the photoreaction tube and then irradiate with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 24 h. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G3 (57.4 mg of colorless oily liquid, yield 64%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.74–7.70 (m, 2H), 7.60–7.52 (m, 3H), 7.45–7.36 (m, 7H), 7.08–7.01 (m, 2H), 6.41 (s, 1H), 4.31 (s, 2H), 0.54 (s, 6H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 162.9 (d, J = 249.1 Hz), 158.0, 157.0, 138.1, 136.5, 134.0, 134.0, 129.7, 129.1, 128.8–128.7 (m, 2C), 128.1, 126.4 (d, J = 3.3 Hz), 125.1, 115.8 (d, J = 21.8 Hz), 108.3, 54.2, –2.9. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.4. 19 19F NMR (376 MHz, CDCl3, 25 °C) δ –112.1––112.2 (m, 1F). IR (ATR): 3067, 2960, 2926, 1599, 1517, 1484, 1320, 1230, 1144, 1085, 939, 839, 783, 738, 701 cm -1 . HRMS (ESI + , m / z): C 25 H 24 FO3SSi + (M + H) + : 451.1194; Found: 451.1197.

[0030] Example 4:

[0031]

[0032] To a dry photoreaction tube equipped with a magnetic stir bar was added A (190.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry DCM (0.5 mL). The photoreaction tube was sealed and then irradiated with a 6 W green LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the green light was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G4 (56.5 mg, colorless oily liquid, yield 61%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.75–7.70 (m, 2H), 7.59–7.52 (m, 3H), 7.43–7.34 (m, 7H), 6.91–6.84 (m, 2H), 6.42 (s, 1H), 4.32 (s, 2H), 3.83 (s, 3H), 0.53 (s, 6H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 159.9, 158.0, 157.2, 138.2, 136.8, 134.0, 133.9, 129.6, 129.0, 128.8, 128.3, 128.0, 125.0, 122.9, 114.2, 107.2, 55.5, 54.4, –2.9. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.5. IR (ATR): 3071, 3004, 2960, 2840, 1614, 1520, 1487, 1305, 1252, 1148, 1085, 1036, 939, 835, 738, 705 cm -1 . HRMS (ESI + , m / z): C 26 H 27 O4SSi + (M + H) +: 463.1394; Found: 463.1393.

[0033] Example 5:

[0034]

[0035] To a dry photoreaction tube equipped with a magnetic stir bar was added A (212.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry DCM (0.2 mL). The photoreaction tube was sealed and then irradiated with a 6 W green LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the green light was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G5 (66.2 mg, colorless oily liquid, yield 66%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.76–7.72 (m, 2H), 7.60–7.58 (m, 4H), 7.58–7.53 (m, 3H), 7.44–7.38 (m, 5H), 6.47 (s, 1H), 4.36 (s, 2H), 0.56 (s, 6H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 159.2, 156.0, 138.0, 136.2, 134.1, 134.0, 133.4, 133.2, 130.2 (q, J = 32.5 Hz), 129.8, 129.2, 128.7, 128.1, 126.7, 125.7 (q, J = 3.7 Hz), 124.1 (q, J = 272.1 Hz), 110.0, 54.1, –3.0. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.1. 19 19F NMR (376 MHz, CDCl3, 25 °C) δ –62.6 (s, 3F). IR (ATR): 3071, 2960, 1621, 1323, 1167, 1118, 1070, 839, 782, 738, 701 cm -1 . HRMS (ESI + , m / z): C 26 H 24 F3O3SSi + (M + H) + : 501.1162; Found: 501.1161.

[0036] Example 6:

[0037]

[0038] To a dry photoreaction tube equipped with a magnetic stir bar was added A (212.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry 1,2-dichloroethane (0.2 mL). The photoreaction tube was sealed and then irradiated with a 6 W green LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the green light was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G6 (70.2 mg of colorless oily liquid, yield 70%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ.74–7.70 (m, 3H), 7.64–7.59 (m, 1H), 7.55–7.49 (m, 4H), 7.47–7.42 (m, 2H), 7.41–7.35 (m, 3H), 7.18–7.14 (m, 1H), 6.55 (s, 1H), 4.14 (s, 2H), 0.53 (s, 6H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 159.1, 155.2, 138.2, 136.4, 134.0, 133.9, 131.8, 131.7, 129.8 (q, J = 31.0 Hz), 129.6, 129.5, 129.2, 128.8, 128.0, 127.8, 127.0 (q, J = 10.3, 5.2 Hz), 123.6 (q, J = 10.3, 274.8 Hz), 123.5, 110.6, 53.6, –3.1. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.0. 19 19F NMR (376 MHz, CDCl3, 25 °C) δ –60.1 (s, 3F). IR (ATR): 3071, 2960, 1621, 1323, 1167, 1118, 1070, 839, 782, 738, 701 cm -1 . HRMS (ESI + , m / z): C 26 H 24 F3O3SSi + (M + H) + : 501.1162; Found: 501.1179.

[0039] Example 7:

[0040]

[0041] To a dry photoreaction tube equipped with a magnetic stir bar, add A (192.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry toluene (0.5 mL). Seal the photoreaction tube and then irradiate with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G7 (65.3 mg, colorless oily liquid, yield 70%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.63–7.60 (m, 2H), 7.58–7.53 (m, 3H), 7.42–7.33 (m, 6H), 7.3–7.26 (m, 1H), 7.19–7.15 (m, 1H), 6.95–6.93 (m, 1H), 6.70 (s, 1H), 4.20 (s, 2H), 0.54 (s, 6H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 159.2, 155.5, 138.1, 136.6, 134.1, 133.8, 133.8, 131.7, 130.5, 130.2, 129.7, 129.0, 128.3, 128.6, 128.0, 126.7, 123.7, 110.9, 53.9, –2.9. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.2. IR (ATR): 3071, 3011, 1636, 1431, 1320, 1144, 1115, 1088, 835, 783, 734, 705 cm -1 . HRMS (ESI + , m / z): C 25 H 24 O3ClSSi + (M + H) +: 467.0899; Found: 467.0898.

[0042] Example 8:

[0043]

[0044] To a dry photoreaction tube equipped with a magnetic stir bar was added A (192.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry DCM (0.5 mL). The photoreaction tube was sealed and then irradiated with a 6 W white LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the white lamp was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G8 (61.6 mg, colorless oily liquid, yield 66%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.74 - 7.72 (m, 2H), 7.61 - 7.52 (m, 3H), 7.44 - 7.37 (m, 7H), 7.34 - 7.30 (m, 2H), 6.42 (s, 1H), 4.32 (s, 2H), 0.54 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 158.3, 156.6, 138.1, 136.4, 134.5, 134.0, 134.0, 129.7, 129.1, 129.0, 128.7, 128.6, 128.1, 127.9, 125.2, 108.9, 54.2, –2.9. 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.2. IR (ATR): 33068, 2960, 1648, 1588, 1476, 1320, 1252, 1148, 1088, 835, 783, 734, 701 cm -1 . HRMS (ESI + , m / z): C 25 H 24 O3ClSSi + (M + H) +: 467.0899; Found: 467.0894.

[0045] Example 9:

[0046]

[0047] To a dry photoreaction tube equipped with a magnetic stir bar was added A (218.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry 1,2-dichloroethane (0.5 mL). The photoreaction tube was sealed and then irradiated with a 6 W white LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the white lamp was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G9 (76.6 mg, colorless oily liquid, yield 75%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.67–7.63 (m, 2H), 7.60–7.58 (m, 4H), 7.42–7.36 (m, 5H), 7.24–7.19 (m, 2H), 6.93–6.88 (m, 1H), 6.69 (s, 1H), 4.18 (s, 2H), 0.55 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.9, 156.8, 138.1, 136.6, 134.1, 133.8, 133.4, 131.9, 130.7, 130.7, 129.6, 129.1, 128.6, 128.0, 127.2, 123.7, 123.6, 110.5, 53.9, –2.9. 29 Si NMR (119 MHz, CDCl3, 25 °C) δ –15.1. IR (ATR): 3064, 2960, 2922, 1584, 1446, 1320, 1252, 1141, 1085, 1029, 939, 835, 783, 738, 701 cm -1 . HRMS (ESI+ , m / z): C 25 H 24 BrO3SSi + (M + H) +: 511.0393; Found: 511.0413.

[0048] Example 10:

[0049]

[0050] Add A (108.9 mg, 0.3 mmol, 3.0 equiv.), B (29.8 mg, 0.1 mmol) and dry toluene (0.25 mL) to a dry photoreaction tube equipped with a magnetic stir bar. Seal the photoreaction tube and then irradiate it with a 6 W white LED lamp. Stir the reaction mixture at room temperature for 12 h. Then turn off the white lamp and concentrate the reaction mixture under reduced pressure. Purify the crude product by silica gel column chromatography (200 - 300 mesh) and elute with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G10 (30.2 mg of colorless oily liquid, yield 59%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.74–7.71 (m, 2H), 7.60–7.53 (m, 3H), 7.49–7.36 (m, 7H), 7.34–7.31 (m, 2H), 6.43 (s, 1H), 4.31 (s, 2H), 0.54 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.4, 156.6, 138.1, 136.4, 134.0, 134.0, 131.9, 129.7, 129.1, 129.0, 128.7, 128.2, 128.1, 125.2, 122.8, 108.9, 54.2, –2.9. 29 Si NMR (119 MHz, CDCl3, 25 °C) δ –15.2. IR (ATR): 3068, 3012, 1960, 1648, 1588, 1476, 1320, 1252, 1144, 1084, 999, 813, 783, 731 cm -1 . HRMS (ESI + , m / z): C 25 H 24 BrO3SSi + (M + H) +: 511.0393; Found: 511.0392.

[0051] Example 11:

[0052]

[0053] To a dry photoreaction tube equipped with a magnetic stir bar was added A (247.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry DCM (0.5 mL). The photoreaction tube was sealed and then irradiated with a 6 W blue LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the blue lamp was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G11 (74.8 mg, colorless oily liquid, yield 67%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.74–7.66 (m, 4H), 7.60–7.52 (m, 3H), 7.44–7.36 (m, 5H), 7.21–7.16 (m, 2H), 6.43 (s, 1H), 4.31 (s, 2H), 0.54 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.5, 156.7, 138.1, 137.9, 136.4, 134.0, 134.0, 129.7, 129.5, 129.1, 128.7, 128.3, 128.1, 125.3, 109.0, 94.4, 54.2, –2.9. 29 Si NMR (119 MHz, CDCl3, 25 °C) δ –15.2. IR (ATR): 3068, 2960, 2922, 1472, 1320, 1148, 1085, 999, 939, 813, 734 cm -1 .HRMS (ESI + , m / z): C 25 H 24 IO3SSi + (M + H) +: 559.0255; Found: 559.0242.

[0054] Example 12:

[0055]

[0056] To a dry photoreaction tube equipped with a magnetic stir bar, add A (217.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry DCM (0.5 mL). Seal the photoreaction tube and then irradiate it with a 6 W ultraviolet lamp. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the ultraviolet lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G12 (70.4 mg of colorless oily liquid, yield 69%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.76–7.73 (m, 2H), 7.62–7.53 (m, 7H), 7.52–7.45 (m, 4H), 7.44–7.36 (m, 6H), 6.50 (s, 1H), 4.41 (s, 2H), 0.57 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.0, 157.5, 141.2, 140.4, 138.1, 136.6, 134.0, 133.9, 129.7, 129.1, 129.0, 128.8, 128.1, 127.8, 127.4, 127.1, 127.1, 125.2, 108.6, 54.3, –2.9. 29 Si NMR (119 MHz, CDCl3, 25 °C) δ –15.3. IR (ATR): 3067, 2960, 2922, 1599, 1480, 1308, 1252, 1144, 1085, 910, 835, 731, 701 cm -1 .HRMS (ESI + , m / z): C 31 H 29 O3SSi + (M + H) +: 509.1601; Found: 509.1603.

[0057] Example 13:

[0058]

[0059] To a dry photoreaction tube equipped with a magnetic stir bar, add A (100.8 mg, 0.3 mmol, 3.0 equiv.), B (29.8 mg, 0.1 mmol) and dry ethyl acetate (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G13 (30.3 mg of colorless oily liquid, yield 63%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.83–7.80 (m, 4H), 7.76–7.73 (m, 2H), 7.62–7.58 (m, 2H), 7.55–7.50 (m, 4H), 7.44–7.34 (m, 5H), 6.59 (s, 1H), 4.45 (s, 2H), 0.59 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 58.2, 157.8, 138.2, 136.6, 134.0, 133.9, 133.2, 133.1, 129.7, 129.0, 128.8, 128.5, 128.4, 128.1, 127.8, 127.5, 126.7, 126.6, 125.8, 125.2, 124.4, 108.9, 54.4, –2.9. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.2. IR (ATR): 3056, 2960, 2922, 1588, 1495, 1428, 1320, 1252, 1148, 1085, 939, 910, 813, 734, 705 cm -1 . HRMS (ESI + , m / z): C 29 H 27 O3SSi + (M + H) +: 483.1445; Found: 483.1442.

[0060] Example 14:

[0061]

[0062] To a dry photoreaction tube equipped with a magnetic stir bar, add A (166.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry tetrahydrofuran (0.5 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G14 (57.1 mg of colorless oily liquid, yield 68%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.67–7.64 (m, 2H), 7.55–7.52 (m, 2H), 7.49–7.44 (m, 1H), 7.42–7.38 (m, 3H), 7.34–7.30 (m, 2H), 7.25 (dd, J = 1.8, 0.8 Hz, 1H), 6.63 (s, 1H), 6.43 (dd, J = 3.5, 0.8 Hz, 1H), 6.32 (dd, J = 3.5, 1.8 Hz, 1H), 4.54 (s, 2H), 0.54 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.3, 149.3, 146.1, 142.2, 137.8, 136.5, 134.0, 133.7, 129.7, 128.7, 128.6, 128.1, 124.9, 111.2, 108.5, 107.6, 53.6, –2.9. 29 Si NMR (79 MHz, CDCl3, 25 °C) δ –14.7. IR (ATR): 3120, 3068, 2960, 1737, 1644, 1320, 1141, 1088, 835, 738, 705 cm -1 . HRMS (ESI + , m / z): C 23 H 23 O4SSi + (M + H) +: 423.1081; Found: 423.1084.

[0063] Example 15:

[0064]

[0065] To a dry photoreaction tube equipped with a magnetic stir bar, add A (175.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry tetrahydrofuran (0.5 mL). Seal the photoreaction tube and then irradiate it with a 6 W blue LED lamp. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the blue lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G15 (61.0 mg, colorless oily liquid, yield 70%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.75–7.71 (m, 2H), 7.57–7.53 (m, 3H), 7.42–7.38 (m, 5H), 7.27 (dd, J = 5.0, 1.2 Hz, 1H), 7.17 (dd, J = 3.7, 1.2 Hz, 1H), 6.99 (dd, J = 5.1, 3.7 Hz, 1H), 6.49 (s, 1H), 4.38 (s, 2H), 0.54 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 158.1, 152.8, 138.0, 136.4, 134.0, 134.0, 131.6, 129.7, 129.0, 128.8, 128.1, 127.6, 126.1, 125.4, 125.0, 108.2, 54.3, –2.9. 29 29Si NMR (79 MHz, CDCl3, 25 °C) δ –14.7. IR (ATR): 3071, 2960, 2922, 1487, 1320, 1252, 1148, 835, 783, 734, 701 cm -1 . HRMS (ESI + , m / z): C 23 H 23 O3S2Si + (M + H) +: 439.0852; Found: 439.0856.

[0066] Example 16:

[0067]

[0068] To a dry photoreaction tube equipped with a magnetic stir bar, add A (150.0 mg, 0.6 mmol, 3.0 equiv.), B (59.6 mg, 0.2 mmol) and dry 1,4-dioxane (0.5 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED light. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G16 (49.6 mg of colorless oily liquid, yield 63%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.68–7.64 (m, 2H), 7.58–7.54 (m, 1H), 7.45–7.37 (m, 4H), 7.36–7.30 (m, 3H), 6.38 (s, 1H), 4.16 (s, 2H), 0.64 (s, 1H), 0.42 (s, 6H), 0.04 (s, 4H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 160.5, 155.3, 138.1, 137.1, 133.9, 133.7, 129.5, 128.9, 128.9, 127.9, 124.0, 107.3, 53.8, 7.3, 6.7, –2.9. 29 29Si NMR (79 MHz, CDCl3, 25 °C) δ –15.4. IR (ATR): 3068, 3008, 2963, 2922, 1610, 1506, 1446, 1308, 1252, 1133, 813, 734, 701 cm -1 . HRMS (ESI + , m / z): C 22 H 25 O3SSi + (M + H) +: 397.1288; Found: 397.1289.

[0069] Example 17:

[0070]

[0071] To a dry photoreaction tube equipped with a magnetic stir bar, add A (102.1 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry acetone (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G17 (32.6 mg, colorless oily liquid, yield 65%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.68–7.65 (m, 2H), 7.57–7.53 (m, 2H), 7.50–7.48 (m, 2H), 7.42–7.37 (m, 3H), 7.30–7.24 (m, 5H), 6.58 (s, 1H), 4.41 (s, 2H), 0.55 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.5, 157.8, 141.1, 136.5, 135.4 (q, J = 33.2 Hz), 133.9, 129.8, 129.7, 129.2, 128.8, 128.7, 128.1, 126.5, 125.9 (q, J = 3.6 Hz), 124.8, 123.1 (q, J = 273.0 Hz), 108.0, 54.0, –3.1. 29 Si NMR (79 MHz, CDCl3, 25 °C) δ –15.3. 19 F NMR (376 MHz, CDCl3, 25 °C) δ –63.1 (s, 3F). IR (ATR): 3068, 2960, 1480, 1405, 1323, 1170, 1141, 1062, 835, 701 cm -1 . HRMS (ESI + , m / z): C 26 H 24 F3O3SSi + (M + H) +: 501.1162; Found: 501.1166.

[0072] Example 18:

[0073]

[0074] To a dry photoreaction tube equipped with a magnetic stir bar, add A (45.4 mg, 0.15 mmol, 3 equiv.), B (19.4 mg, 0.05 mmol) and dry DCM (0.13 mL). Seal the photoreaction tube and then irradiate it with a 6 W white LED lamp. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the white lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G18 (15.0 mg of colorless oily liquid, yield 65%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.60–7.54 (m, 4H), 7.42–7.37 (m, 5H), 7.35–7.29 (m, 3H), 6.82–6.78 (m, 2H), 6.53 (s, 1H), 4.34 (s, 2H), 3.81 (s, 3H), 0.55 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 163.9, 157.8, 157.6, 136.7, 134.0, 130.9, 130.2, 129.6, 129.5, 128.7, 128.5, 128.1, 126.7, 125.2, 114.1, 108.9, 55.7, 54.4, –2.9. 29 29Si NMR (119 MHz, CDCl3, 25 °C) δ –15.4. IR (ATR): 3064, 2960, 2844, 1595, 1498, 1320, 1260, 1141, 1025, 835, 782, 734, 697 cm -1 . HRMS (ESI + , m / z): C 26 H 27 O4SSi + (M + H) +: 463.1394; Found: 463.1410.

[0075] Example 19:

[0076]

[0077] To a dry photoreaction tube equipped with a magnetic stir bar, add A (202 mg, 0.6 mmol, 3 equiv.), B (59.6 mg, 0.2 mmol) and dry methyl tert-butyl ether (0.5 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED light. The reaction mixture is stirred at room temperature for 12 h. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G19 (70.8 mg of colorless oily liquid, yield 73%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 8.20 (d, J = 1.8 Hz, 1H), 7.86 (dd, J = 8.3, 1.1 Hz, 1H), 7.80–7.75 (m, 2H), 7.69–7.63 (m, 2H), 7.60–7.56 (m, 1H), 7.51–7.48 (m, 2H), 7.41–7.33 (m, 3H), 7.29–7.26 (m, 2H), 7.20–7.17 (m, 3H), 6.45 (s, 1H), 4.43 (s, 2H), 0.48 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 157.9, 157.8, 136.5, 135.5, 134.6, 134.0, 132.0, 130.9, 129.9, 129.6, 129.5, 129.4, 129.1, 128.5, 128.4, 128.0, 128.0, 127.6, 126.6, 125.1, 123.1, 108.5, 54.3, –3.0. 29 Si NMR (119 MHz, CDCl3, 25 °C) δ –15.5. IR (ATR): 3056, 2960, 1592, 1480, 1316, 1252, 1126, 939, 910, 880, 816, 783, 697 cm - 1 . HRMS (ESI + , m / z): C 29 H 27 O3SSi + (M + H) +: 483.1445; Found: 483.1439.

[0078] Example 20:

[0079]

[0080] To a dry photoreaction tube equipped with a magnetic stir bar, add A (91.2 mg, 0.3 mmol, 3 equiv.), B (529.8 mg, 0.1 mmol) and dry DCM (0.1 mL). Seal the photoreaction tube and then irradiate it with a 6 W blue LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the blue lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G20 (36.7 mg of colorless oily liquid, yield 82%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.65–7.61 (m, 2H), 7.57–7.54 (m, 2H), 7.45–7.32 (m, 8H), 7.01–6.94 (m, 2H), 6.52 (s, 1H), 4.37 (s, 2H), 0.56 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 166.0 (d, J=256.6 Hz), 158.2, 157.7, 136.5, 134.0, 133.8 (d, J=3.1 Hz), 131.5 (d, J=9.6 Hz), 130.0, 129.7, 128.7, 128.6, 128.1, 126.6, 125.0, 116.2 (d, J=22.7 Hz), 108.4, 54.2, –3.0. 29 Si NMR (119 MHz, CDCl3, 25 °C) δ –15.3. 19 F NMR (376 MHz, CDCl3, 25 °C) δ –103.1––103.3 (m, 1F). IR (ATR): 3071, 2960, 2926, 1592, 1491, 1405, 1323, 1290, 1234, 1144, 1115, 1088, 943, 876, 835, 783, 738, 701 cm -1 . HRMS (ESI + , m / z): C 25 H 24 FO3SSi + (M + H) +: 451.1194; Found: 451.1191.

[0081] Example 21:

[0082]

[0083] To a dry photoreaction tube equipped with a magnetic stir bar, add A (96.0 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry DCM (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W white LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the white lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G21 (32.5 mg of colorless oily liquid, yield 70%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.58–7.54 (m, 2H), 7.53–7.49 (m, 2H), 7.43–7.37 (m, 3H), 7.35–7.29 (m, 5H), 7.25–7.22 (m, 2H), 6.54 (s, 1H), 4.37 (s, 2H), 0.56 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.2, 157.7, 140.7, 136.5, 136.1, 134.0, 130.1, 129.9, 129.7, 129.2, 128.7, 128.6, 128.1, 126.6, 124.9, 108.3, 54.1, –3.0. 29 Si NMR (79 MHz, CDCl3, 25 °C) δ –15.3. IR (ATR): 3068, 2960, 2926, 1580, 1476, 1320, 1252, 1141, 1014, 939, 812, 779, 734, 701 cm -1 . HRMS (ESI + , m / z): C 25 H 24 ClO3SSi + (M + H) +: 467.0899; Found: 467.0897.

[0084] Example 22:

[0085]

[0086] To a dry photoreaction tube equipped with a magnetic stir bar, add A (108.9 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry chloroform (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G22 (32.0 mg of colorless oily liquid, yield 63%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.58–7.54 (m, 2H), 7.45–7.39 (m, 7H), 7.36–7.30 (m, 5H), 6.55 (s, 1H), 4.37 (s, 2H), 0.57 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.3, 157.7, 136.6, 136.5, 134.0, 132.2, 130.1, 129.9, 129.8, 129.4, 128.7, 128.7, 128.1, 126.6, 124.9, 108.3, 54.1, –3.0. 29 Si NMR (79 MHz, CDCl3, 25 °C) δ –15.3. IR (ATR): 3071, 2960, 2922, 1573, 1480, 1428, 1323, 1252, 1141, 1114, 1066, 1010, 939, 876, 813, 779, 738, 701 cm -1 . HRMS (ESI + , m / z): C 25 H 24 BrO3SSi + (M + H) +: 511.0393; Found: 511.0384.

[0087] Example 23:

[0088]

[0089] To a dry photoreaction tube equipped with a magnetic stir bar, add A (180.0 mg, 0.6 mmol, 3 equiv.), B (59.6 mg, 0.2 mmol) and dry carbon tetrachloride (0.5 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G23 (66.3 mg of colorless oily liquid, yield 76%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.61–7.57 (m, 3H), 7.48–7.46 (m, 1H), 7.44–7.33 (m, 8H), 7.01–6.99 (m, 1H), 6.60 (s, 1H), 4.47 (s, 2H), 0.57 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.0, 157.9, 138.7, 136.6, 135.0, 134.7, 134.0, 130.1, 129.7, 128.8, 128.6, 128.1, 127.9, 126.7, 124.9, 108.5, 55.5, –2.9. 29 Si NMR (79 MHz, CDCl3, 25 °C) δ –15.3. IR (ATR): 3094, 3071, 2960, 2926, 1592, 1480, 1428, 1320, 1252, 1137, 1014, 939, 835, 779, 731, 697 cm -1 . HRMS (ESI + , m / z): C 23 H 23 O3S2Si + (M + H) + : 439.0852; Found: 439.0845.

[0090] Example 24:

[0091]

[0092] To a dry photoreaction tube equipped with a magnetic stir bar, add A (62.4 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry benzene (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED light. The reaction mixture is stirred at room temperature for 24 hours. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE to obtain the target compound G24 (23.4 mg of colorless oily liquid, yield 66%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.67–7.64 (m, 2H), 7.56–7.54 (m, 2H), 7.41–7.37 (m, 5H), 7.34–7.32 (m, 2H), 7.29–7.26 (m, 3H), 7.24–7.22 (m, 1H), 6.78 (s, 1H), 0.61 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 157.3, 153.1, 136.9, 134.7, 134.2, 131.6, 129.6, 128.8, 128.7, 128.5, 128.1, 127.7, 127.1, 126.5, 125.5, 122.7, -2.7. 29 29Si NMR (79 MHz, CDCl3, 25 °C) δ –15.6. IR (ATR): 3068, 2960, 1603, 1198, 1427, 1252, 1118, 1070, 943, 834, 764, 697 cm -1 . HRMS (ESI + , m / z): C 24 H 23 OSSi + (M + H) + : 355.1513; Found: 355.1514.

[0093] Example 25:

[0094]

[0095] To a dry photoreaction tube equipped with a magnetic stir bar, add A (66.6 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry DCM (0.1 mL). Seal the photoreaction tube and then irradiate it with a 6 W white LED lamp. The reaction mixture is stirred at room temperature for 24 h. Then turn off the white lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE to obtain the target compound G25 (24.1 mg of colorless oily liquid, yield 65%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.68 - 7.63 (m, 2H), 7.56 - 7.54 (m, 2H), 7.40 - 7.26 (m, 8H), 7.15 (d, J = 7.7 Hz, 2H), 6.76 (s, 1H), 2.37 (s, 3H), 0.61 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 157.1, 152.9, 137.0, 136.8, 134.2, 131.6, 129.6, 129.4, 128.6, 128.4, 128.0, 127.7, 127.6, 126.4, 125.6, 122.6, 21.4, –2.7. IR (ATR): 3068, 2960, 2919, 1513, 1428, 1252, 1115, 943, 813, 783, 734, 697 cm -1 . HRMS (ESI + , m / z): C 25 H 25 OSi + (M + H) + : 369.1669; Found: 369.1658.

[0096] Example 26:

[0097]

[0098] To a dry photoreaction tube equipped with a magnetic stir bar, add A (66.6 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry DCM (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 24 h. Then turn off the green lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE to obtain the target compound G26 (24.7 mg of colorless oily liquid, yield 61%). 11H NMR (400 MHz, CDCl3, 25 °C) δ 7.66–7.64 (m, 2H), 7.59–7.54 (m, 2H), 7.40–7.22 (m, 9H), 7.10 (d, J = 7.2 Hz, 1H), 6.76 (s, 1H), 2.33 (s, 3H), 0.61 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 157.2, 153.0, 138.3, 137.0, 135.9, 134.6, 134.2, 131.6, 129.6, 129.5, 128.6, 128.4, 127.8, 127.6, 126.4, 125.9, 125.7, 122.8, 21.5, –2.7. IR (ATR): 3056, 2960, 2919, 1607, 1428, 1252, 1115, 943, 835, 783, 734 cm -1 . HRMS (ESI + , m / z): C 25 H 25 OSi + (M + H) + : 369.1669; Found: 369.1658.

[0099] Example 27:

[0100]

[0101] To a dry photoreaction tube equipped with a magnetic stir bar was added A (66.6 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry DCM (0.25 mL). The photoreaction tube was sealed and then irradiated with a 6 W green LED lamp. The reaction mixture was stirred at room temperature for 24 h. Then the green light was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200–300 mesh) and eluted with PE to give the target compound G27 (23.3 mg of colorless oily liquid, yield 63%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.67–7.65 (m, 2H), 7.43–7.38 (m, 5H), 7.28–7.17 (m, 7H), 6.66 (s, 1H), 2.14 (s, 3H), 0.62 (s, 6H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 156.7, 152.8, 137.1, 137.0, 134.6, 134.2, 131.7, 130.4, 130.3, 129.6, 128.5, 128.1, 127.7, 127.2, 126.3, 126.1, 125.0, 121.9, 20.3, –2.6. IR (ATR): 3067, 3019, 2960, 1602, 1495, 1428, 1252, 1115, 943, 835, 764, 731, 693 cm -1 . HRMS (ESI + , m / z): C 25 H 24 OSi + (M) + : 368.1591; Found: 368.1583.

[0102] Example 28:

[0103]

[0104] To a dry photoreaction tube equipped with a magnetic stir bar was added A (72.6 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry DCM (0.25 mL). The photoreaction tube was sealed and then irradiated with a 6 W green LED lamp. The reaction mixture was stirred at room temperature for 24 h. Then the green light was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE to give the target compound G28 (23.0 mg, colorless oil, yield 60%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.69 – 7.65 (m, 2H), 7.57 – 7.53 (m, 2H), 7.44 – 7.39 (m, 3H), 7.35 – 7.27 (m, 7H), 6.77 (s, 1H), 0.64 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 157.7, 153.3, 136.8, 134.1, 133.1, 132.9, 131.3, 130.1, 129.7, 128.9, 128.6, 128.1, 127.9, 126.6, 125.1, 121.5, –2.7. IR (ATR): 3068, 2960, 1603, 1495, 1428, 1252, 1096, 1014, 943, 813, 783, 734, 693 cm -1 . HRMS (ESI +, m / z): C 24 H 22 ClOSi + (M + H) + : 389.1123; Found: 389.1136.

[0105] Example 29:

[0106]

[0107] Add A (85.2 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry DCM (0.25 mL) to a dry photoreaction tube equipped with a magnetic stir bar. Seal the photoreaction tube and then irradiate it with a 6 W white LED lamp. Stir the reaction mixture at room temperature for 24 h. Then turn off the white lamp and concentrate the reaction mixture under reduced pressure. Purify the crude product by silica gel column chromatography (200 - 300 mesh) and elute with PE to obtain the target compound G29 (28.1 mg of colorless oily liquid, yield 65%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.69–7.58 (m, 8H), 7.50–7.28 (m, 11H), 6.83 (s, 1H), 0.63 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 157.5, 153.2, 140.8, 139.8, 136.9, 134.2, 131.6, 129.6, 129.1, 128.9, 128.5, 128.1, 127.8, 127.8, 127.4, 127.4, 127.1, 126.6, 125.4, 122.2, –2.7. IR (ATR): 3060, 2960, 2926, 2855, 1808, 1756, 1602, 1491, 1252, 1118, 943, 831, 768, 731, 697 cm -1 . HRMS (ESI + , m / z): C 30 H 27 F3OSi + (M + H) + : 431.1826; Found: 431.1832.

[0108] Example 30:

[0109]

[0110] Add A (71.4 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry DCM (0.1 mL) to a dry photoreaction tube equipped with a magnetic stir bar. Seal the photoreaction tube and then irradiate it with a 6 W blue LED lamp. The reaction mixture is stirred at room temperature for 24 h. Then turn off the blue lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE to give the target compound G30 (23.2 mg of colorless oily liquid, yield 63%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.68–7.63 (m, 2H), 7.58–7.54 (m, 2H), 7.41–7.39 (m, 3H), 7.34–7.24 (m, 5H), 6.91–6.85 (m, 2H), 6.75 (s, 1H), 3.83 (s, 3H), 0.61 (s, 6H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 158.8, 157.1, 152.7, 137.0, 134.2, 131.7, 129.9, 129.6, 128.4, 128.0, 127.5, 126.9, 126.3, 125.6, 122.3, 114.1, 55.4, –2.7. IR (ATR): 3071, 3004, 2960, 2837, 1592, 1513, 1290, 1249, 1179, 1115, 1036, 943, 813, 701 cm -1 . HRMS (ESI + , m / z): C 25 H 24 OSi + (M + H) + : 385.1615; Found: 385.1618.

[0111] Example 31:

[0112]

[0113] Add A (77.4 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry DCM (0.25 mL) to a dry photoreaction tube equipped with a magnetic stir bar. Seal the photoreaction tube and then irradiate it with a 6 W UV LED lamp. The reaction mixture is stirred at room temperature for 24 h. Then turn off the UV lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE to give the target compound G31 (25.1 mg of colorless oily liquid, yield 62%). 11H NMR (400 MHz, CDCl3, 25 °C) δ 7.90–7.88 (m, 1H), 7.86–7.74 (m, 3H), 7.70–7.65 (m, 2H), 7.60–7.55 (m, 2H), 7.51–7.45 (m, 3H), 7.41 (dd, J=4.9, 1.8 Hz, 3H), 7.26 (s, 3H), 6.88 (s, 1H), 0.64 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 157.5, 153.4, 136.9, 134.2, 133.8, 132.5, 132.2, 131.5, 129.6, 128.5, 128.2, 128.1, 128.0, 127.8, 127.8, 127.3, 127.2, 126.6, 126.3, 125.9, 125.6, 122.6, –2.7. IR (ATR): 3056, 2956, 2926, 2851, 1602, 1484, 1428, 1252, 1115, 943, 813, 783, 734, 701 cm -1 . HRMS (ESI + , m / z): C 28 H 25 OSi + (M + H) + : 405.1669; Found: 405.1658.

[0114] Example 32:

[0115]

[0116] To a dry photoreaction tube equipped with a magnetic stir bar was added A (100.0 mg, 0.6 mmol, 3 equiv.), B (59.6 mg, 0.2 mmol) and dry 1,2-dichloroethane (0.5 mL). The photoreaction tube was sealed and then irradiated with a 6 W green LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the green light was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE to give the target compound G32 (40.2 mg of colorless oily liquid, yield 64%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.96–7.92 (m, 2H), 7.61–7.58 (m, 2H), 7.45–7.38 (m, 5H), 7.34–7.29 (m, 1H), 6.68 (s, 1H), 0.59 (s, 6H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 157.5, 151.5, 136.2, 134.1, 129.9, 129.8, 128.6, 128.1, 128.0, 125.3, 124.9, 111.9, –2.9. IR (ATR): 3071, 2960, 2926, 1607, 1476, 1428, 1252, 1118, 1074, 969, 936, 812, 734, 693 cm -1 . HRMS (ESI + , m / z): C 18 H 17 ClOSi + (M) + : 312.0732; Found: 312.0739.

[0117] Example 33:

[0118]

[0119] To a dry photoreaction tube equipped with a magnetic stir bar was added A (61.2 mg, 0.3 mmol, 3 equiv.), B (29.8 mg, 0.1 mmol) and dry ethyl acetate (0.25 mL). The photoreaction tube was sealed and then irradiated with a 6 W green LED lamp. The reaction mixture was stirred at room temperature for 24 h. Then the green light was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G33 (19.6 mg, colorless oily liquid, yield 56%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.64 - 7.60 (m, 4H), 7.44 - 7.37 (m, 5H), 7.34 - 7.29 (m, 1H), 6.73 (s, 1H), 3.73 (s, 3H), 3.64 (s, 2H), 0.58 (s, 6H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 172.0, 157.2, 155.0, 137.0, 134.1, 131.2, 129.5, 128.7, 128.0, 127.8, 126.4, 125.4, 113.5, 52.3, 31.9, –2.7. IR (ATR): 2956, 2922, 2855, 1744, 1476, 1431, 1252, 1118, 947, 835, 783, 734, 701 cm -1 . HRMS (ESI + , m / z): C 21 H23 O3Si + (M + H) + : 351.1411; Found: 351.1398.

[0120] Example 34:

[0121]

[0122] Add A (85.8 mg, 0.3 mmol, 3 equiv.), B (17.8 mg, 0.1 mmol) and dry DCM (0.25 mL) to a dry photoreaction tube equipped with a magnetic stir bar. Seal the photoreaction tube and then irradiate it with a 6 W blue LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the blue lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G34 (25.4 mg of white solid, yield 68%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.81–7.74 (m, 2H), 7.70–7.64 (m, 2H), 7.61–7.55 (m, 1H), 7.47–7.29 (m, 10H), 6.65 (s, 1H), 4.42 (s, 2H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 153.1, 152.6, 138.0, 134.1, 130.1, 129.7, 129.2, 128.9, 128.8, 128.7, 128.5, 128.0, 126.6, 124.0, 110.4, 109.0, 54.3. IR (ATR): 3064, 2930, 1595, 1491, 1446, 1320, 1152, 1085, 910, 764, 690. cm -1 . HRMS (ESI + , m / z): C 23 H 19 O3S + (M + H) + : 375.1049; Found: 375.1038.

[0123] Example 35:

[0124]

[0125] Add A (86.0 mg, 0.3 mmol, 3 equiv.), B (25.4 mg, 0.1 mmol) and dry DCM (0.25 mL) to a dry photoreaction tube equipped with a magnetic stir bar. Seal the photoreaction tube and then irradiate it with a 6 W white LED lamp. Stir the reaction mixture at room temperature for 12 h. Then turn off the white lamp and concentrate the reaction mixture under reduced pressure. Purify the crude product by silica gel column chromatography (200 - 300 mesh) and elute with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G35 (35.0 mg of white solid, yield 78%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.80–7.74 (m, 4H), 7.67–7.57 (m, 5H), 7.49–7.33 (m, 10H), 6.70 (s, 1H), 4.43 (s, 2H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 152.9, 152.7, 140.7, 140.5, 138.0, 134.1, 129.7, 129.2, 129.0, 129.0, 128.8, 128.7, 128.6, 127.7, 127.6, 127.1, 126.6, 124.4, 110.6, 109.2, 54.3. IR (ATR): 3064, 3030, 2922, 1599, 1483, 1446, 1319, 1152, 1085, 768 cm -1 . HRMS (ESI + , m / z): C 29 H 23 O3S + (M + H) + : 451.1362; Found: 451.1364.

[0126] Example 36:

[0127]

[0128] Add A (86.0 mg, 0.3 mmol, 3 equiv.), B (19.2 mg, 0.1 mmol) and dry toluene (0.25 mL) to a dry photoreaction tube equipped with a magnetic stir bar. Seal the photoreaction tube and then irradiate it with a 6 W blue LED lamp. Stir the reaction mixture at room temperature for 12 h. Then turn off the blue lamp and concentrate the reaction mixture under reduced pressure. Purify the crude product by silica gel column chromatography (200 - 300 mesh) and elute with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G36 (27.5 mg of colorless oily liquid, yield 71%). 11H NMR (400 MHz, CDCl3, 25 °C) δ 7.78–7.76 (m, 2H), 7.57–7.55 (m, 3H), 7.45–7.19 (m, 10H), 6.59 (s, 1H), 4.41 (s, 2H), 2.38 (s, 3H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 153.3, 152.2, 138.0, 138.0, 134.1, 129.8, 129.6, 129.2, 128.8, 128.7, 128.4, 127.4, 126.5, 124.0, 110.3, 108.3, 54.3, 21.5. IR (ATR): 3060, 3030, 2922, 1502, 1446, 1320, 1156, 1085, 813, 690 cm -1 . HRMS (ESI + , m / z): C 24 H 21 O3S + (M + H) + : 389.1206; Found: 389.1204.

[0129] Example 37:

[0130]

[0131] To a dry photoreaction tube equipped with a magnetic stir bar was added A (86.0 mg, 0.3 mmol, 3 equiv.), B (19.2 mg, 0.1 mmol) and dry DCM (0.25 mL). The photoreaction tube was sealed and then irradiated with a 6 W blue LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the blue lamp was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G37 (27.5 mg, colorless oil, 71% yield). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.76–7.78 (m, 2H), 7.60–7.53 (m, 1H), 7.53–7.40 (m, 4H), 7.40–7.27 (m, 6H), 7.15–7.09 (m, 1H), 6.66 (s, 1H), 4.41 (s, 2H), 2.40 (s, 3H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 153.3, 152.5, 138.6, 138.0, 134.1, 130.0, 129.7, 129.2, 128.8, 128.8, 128.8, 128.7, 128.5, 126.5, 124.6, 121.2, 110.4, 108.9, 54.3, 21.6. IR (ATR): 3056, 2922, 1599, 1491, 1446, 1319, 1155, 1085, 786, 693 cm -1 . HRMS (ESI + , m / z): C 24 H 21 O3S + (M + H) + : 389.1206; Found: 389.1202.

[0132] Example 38:

[0133]

[0134] To a dry photoreaction tube equipped with a magnetic stir bar was added A (86.0 mg, 0.3 mmol, 3 equiv.), B (19.2 mg, 0.1 mmol) and dry DCM (0.25 mL). The photoreaction tube was sealed and then irradiated with a 6 W blue LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the blue lamp was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G38 (23.3 mg, colorless oily liquid, yield 60%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.81–7.78 (m, 2H), 7.72–7.70 (m, 1H), 7.61–7.56 (m, 1H), 7.48–7.43 (m, 4H), 7.39–7.31 (m, 3H), 7.29–7.22 (m, 3H), 6.45 (s, 1H), 4.45 (s, 2H), 2.47 (s, 3H). 1313C NMR (151 MHz, CDCl3, 25 °C) δ 152.7, 152.3, 138.1, 134.8, 134.0, 131.4, 129.2, 128.8, 128.7, 128.5, 128.0, 127.0, 126.5, 126.2, 112.5, 110.0, 54.3, 22.2. IR (ATR): 3060, 2974, 2926, 1595, 1491, 1320, 1148, 1085, 910, 760, 690 cm -1 . HRMS (ESI + , m / z): C 24 H 21 O3S + (M + H) + : 389.1206; Found: 389.1208.

[0135] Example 39:

[0136]

[0137] To a dry photoreaction tube equipped with a magnetic stir bar was added A (86.0 mg, 0.3 mmol, 3 equiv.), B (19.3 mg, 0.1 mmol) and dry DCM (0.25 mL). The photoreaction tube was sealed and then irradiated with a 6 W blue LED lamp. The reaction mixture was stirred at room temperature for 12 h. Then the blue lamp was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G39 (29.5 mg of white solid, yield 75%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.80–7.75 (m, 2H), 7.68–7.61 (m, 2H), 7.60–7.55 (m, 1H), 7.47–7.41 (m, 2H), 7.40–7.30 (m, 5H), 7.13–7.06 (m, 2H), 6.61 (s, 1H), 4.40 (s, 2H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 162.5 (d, J = 247.9 Hz), 152.7, 152.3, 138.1, 134.1, 129.6, 129.2, 128.8, 128.7, 128.6, 126.6, 126.5 (d, J = 3.4 Hz), 125.8 (d, J = 8.1 Hz), 116.0 (d, J = 21.9 Hz), 110.4, 108.7, 54.2. 1919F NMR (151 MHz, CDCl3, 25 °C) δ –113.1 ––113.2 (m, 1F). IR (ATR): 3064, 2930, 1498, 1446, 1319, 1230, 1155, 1085, 839, 686 cm -1 . HRMS (ESI + , m / z): C 23 H 18 FO3S + (M + H) + : 393.0955; Found: 393.0950.

[0138] Example 40:

[0139]

[0140] To a dry photoreaction tube equipped with a magnetic stir bar was added A (86.0 mg, 0.3 mmol, 3 equiv.), B (21.2 mg, 0.1 mmol) and dry DCM (0.25 mL). The photoreaction tube was sealed and then irradiated with a 6 W UV lamp. The reaction mixture was stirred at room temperature for 12 h. Then the UV lamp was turned off and the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G40 (28.6 mg of white solid, yield 70%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.83 – 7.74 (m, 2H), 7.61 – 7.56 (m, 3H), 7.47 – 7.42 (m, 2H), 7.40 – 7.31 (m, 7H), 6.66 (s, 1H), 4.40 (s, 2H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 152.9, 152.0, 138.1, 134.1, 133.6, 129.5, 129.2, 129.1, 128.8, 128.7, 128.7, 128.6, 126.6, 125.2, 110.5, 109.5, 54.1. IR (ATR): 3064, 2926, 1480, 1308, 1148, 1088, 1010, 910, 813, 731, 686 cm -1 . HRMS (ESI + , m / z): C 23 H 18 ClO3S + (M + H) + : 409.0660; Found: 409.0662.

[0141] Example 41:

[0142]

[0143] To a dry photoreaction tube equipped with a magnetic stir bar, add A (86.0 mg, 0.3 mmol, 3 equiv.), B (25.6 mg, 0.1 mmol) and dry 1,2-dichloroethane (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W blue LED lamp. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the blue lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G41 (28.9 mg of white solid, yield 64%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.81–7.75 (m, 2H), 7.61–7.51 (m, 5H), 7.47–7.42 (m, 2H), 7.40–7.32 (m, 5H), 6.68 (s, 1H), 4.40 (s, 2H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 153.0, 152.1, 138.1, 134.1, 132.1, 129.5, 129.2, 129.0, 128.9, 128.7, 128.7, 126.6, 125.5, 121.8, 110.5, 109.6, 54.2. IR (ATR): 3418, 3370, 1655, 1491, 1446, 1305, 1148, 1085, 1021, 850, 813, 760, 682 cm -1 . HRMS (ESI + , m / z): C 23 H 18 BrO3S + (M + H) + : 453.0155; Found: 453.0158.

[0144] Example 42:

[0145]

[0146] To a dry photoreaction tube equipped with a magnetic stir bar, add A (86.0 mg, 0.3 mmol, 3 equiv.), B (24.6 mg, 0.1 mmol) and dry DCM (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W green LED lamp. The reaction mixture is stirred at room temperature for 12 hours. Then turn off the green light and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to obtain the target compound G42 (26.1 mg of white solid, yield 64%). 1 1H NMR (400 MHz, CDCl3, 25 °C) δ 7.81–7.74 (m, 4H), 7.65 (d, J = 8.4 Hz, 2H), 7.62–7.57 (m, 1H), 7.48–7.34 (m, 7H), 6.80 (s, 1H), 4.41 (s, 2H). 13 13C NMR (151 MHz, CDCl3, 25 °C) δ 153.7, 151.5, 138.0, 134.2, 133.2, 129.5 (q, J = 32.6 Hz), 129.3, 129.3, 128.9, 128.9, 128.6, 126.7, 125.9 (q, J = 3.8 Hz), 124.2 (q, J = 271.7 Hz), 124.0, 111.0, 110.7, 54.1. 19 19F NMR (376 MHz, CDCl3, 25 °C) δ –62.4 (s, 3F). IR (ATR): 3064, 2930, 1618, 1320, 1152, 1111, 1014, 910, 842, 768, 731, 686 cm -1 . HRMS (ESI + , m / z): C 24 H 18 F3O3S + (M + H) + : 443.0923; Found: 443.0925.

[0147] Example 43:

[0148]

[0149] To a dry photoreaction tube equipped with a magnetic stir bar, add A (86.0 mg, 0.3 mmol, 3 equiv.), B (38.0 mg, 0.1 mmol) and dry DCM (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W blue LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the blue lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G43 (32.0 mg as a white solid, yield 75%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 8.17–8.14 (m, 1H), 7.91–7.76 (m, 5H), 7.76–7.72 (m, 1H), 7.61–7.55 (m, 1H), 7.55–7.41 (m, 6H), 7.41–7.29 (m, 3H), 6.79 (s, 1H), 4.45 (s, 2H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 153.2, 152.9, 138.0, 134.1, 133.5, 133.0, 129.7, 129.2, 128.9, 128.7, 128.7, 128.6, 128.3, 127.9, 127.4, 126.8, 126.6, 126.3, 122.5, 122.2, 110.6, 109.7, 54.3. IR (ATR): 3056, 2922, 1599, 1491, 1446, 1319, 1155, 1085, 786, 693 cm -1 . HRMS (ESI + , m / z): C 24 H 21 O3S + (M + H) + : 425.1206; Found: 425.1202.

[0150] Example 44:

[0151]

[0152] To a dried photoreaction tube equipped with a magnetic stir bar, add A (86.0 mg, 0.3 mmol, 3 equiv.), B (18.4 mg, 0.1 mmol) and dry DCM (0.25 mL). Seal the photoreaction tube and then irradiate it with a 6 W blue LED lamp. The reaction mixture is stirred at room temperature for 12 h. Then turn off the blue lamp and concentrate the reaction mixture under reduced pressure. The crude product is purified by silica gel column chromatography (200 - 300 mesh) and eluted with PE / EA (20 / 1 - 10 / 1, v / v) to give the target compound G44 (24.0 mg as a white solid, yield 62%). 1 H NMR (400 MHz, CDCl3, 25 °C) δ 7.78 (dd, J = 8.4, 1.3 Hz, 2H), 7.60–7.56 (m, 1H), 7.48–7.43 (m, 2H), 7.39–7.26 (m, 7H), 7.06 (dd, J = 5.1, 3.6 Hz, 1H), 6.49 (s, 1H), 4.39 (s, 2H). 13 C NMR (151 MHz, CDCl3, 25 °C) δ 152.2, 148.8, 138.0, 134.1, 133.0, 129.4, 129.2, 128.8, 128.7, 128.6, 127.9, 126.6, 125.0, 123.4, 110.4, 108.8, 54.2. IR (ATR): 3109, 3064, 2922, 1599, 1446, 1320, 1152, 1085, 1021, 910, 768, 734, 690 cm -1 . HRMS (ESI + , m / z): C 21 H 17 O3S2 + (M + H) + : 386.0614; Found: 386.0615.

[0153] The above are the preferred embodiments of the present invention. Of course, the scope of the rights of the present invention cannot be limited thereby. It should be pointed out that for those of ordinary skill in the art, without departing from the principle of the present invention, several improvements and changes can be made, and these improvements and changes are also regarded as the protection scope of the present invention.

Claims

1. A method for synthesizing a furan compound, characterized in that: Mix α,β-unsaturated ketone A, acylsilane B and an organic solvent, stir and react the mixed solution under light irradiation at 0 - 30 °C, and then separate and purify to obtain the said furan compound; The molecular structural formula of the said furan compound is as follows: ； The molecular structural formula of the α,β-unsaturated ketone A is ; The molecular structural formula of the acylsilane B is as follows: ; wherein R 1 and R 2 are each independently an alkyl group, which may be the same or different; R 3 is an alkyl group; R 4 , R 5 and R 6 are each independently an alkyl group, which may be the same or different; the alkyl group has 1 to 20 carbon atoms and is a straight-chain or branched-chain structure; The organic solvent is at least one of methanol, ethanol, isopropanol, tert-butanol, tetrahydrofuran, 2-methyltetrahydrofuran, diethyl ether, dimethoxyethane, methyl tert-butyl ether, 1,4-hexylene oxide, 1,3-hexylene oxide, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, 3-12 fluorinated or chlorinated alkanes, benzene, toluene, xylene, trimethylbenzene, dimethyl sulfoxide, N , N N,N-dimethylformamide, N , N N,N-dimethylacetamide, acetone, N N-methylpyrrolidone, acetonitrile, 3-12 saturated alkyl nitriles; The light source for the said light irradiation is any one of white light, blue light, purple light, green light, and sunlight, and the power of the light source is between 1 W and 60 W.

2. A method for synthesizing a furan compound, characterized in that: Mix α,β-unsaturated ketone A, acylsilane B and an organic solvent, stir and react the mixed solution under light irradiation at 0 - 30 °C, and then separate and purify to obtain the said furan compound; The molecular structural formula of the said furan compound is as follows: ； The molecular structural formula of the α,β-unsaturated ketone A is ; The molecular structural formula of the acylsilane B is as follows: ; Among them, the structure of the acylsilane B is: ; the structure of the furan compound is: ； The organic solvent is at least one of methanol, ethanol, isopropanol, tert-butanol, tetrahydrofuran, 2-methyltetrahydrofuran, diethyl ether, dimethoxyethane, methyl tert-butyl ether, 1,4-hexylene oxide, 1,3-hexylene oxide, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, 3-12 fluorinated or chlorinated alkanes, benzene, toluene, xylene, mesitylene, dimethyl sulfoxide, N , N N,N-dimethylformamide, N , N N,N-dimethylacetamide, acetone, N N-methylpyrrolidone, acetonitrile, 3-12 saturated alkyl nitriles; The light source for the said light irradiation is any one of white light, blue light, purple light, green light, and sunlight, and the power of the light source is between 1 W and 60 W.

3. A method for synthesizing a furan compound, characterized in that: Mix α,β-unsaturated ketone A, acylsilane B and an organic solvent, stir and react the mixed solution under light irradiation at 0 - 30 °C, and then separate and purify to obtain the said furan compound; The molecular structural formula of the said furan compound is as follows: ； The molecular structural formula of the α,β-unsaturated ketone A is ; The molecular structural formula of the acylsilane B is as follows: ; Among them, R4, R5, and R6 are all methyl groups; the structure of the furan compound is: , The organic solvent is at least one of methanol, ethanol, isopropanol, tert-butanol, tetrahydrofuran, 2-methyltetrahydrofuran, diethyl ether, dimethoxyethane, methyl tert-butyl ether, 1,4-hexylene oxide, 1,3-hexylene oxide, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, C 3-12 fluorinated or chlorinated alkanes, benzene, toluene, xylene, mesitylene, dimethyl sulfoxide, N , N N,N-dimethylformamide, N , N N,N-dimethylacetamide, acetone, N N-methylpyrrolidone, acetonitrile, C 3-12 saturated alkyl nitriles; The light source for the said light irradiation is any one of white light, blue light, purple light, green light, and sunlight, and the power of the light source is between 1 W and 60 W.

4. The method for synthesizing a furan compound according to any one of claims 1 - 3, characterized in that: The molar ratio between α,β-unsaturated ketone A and acylsilane B is 1 - 6:1; the concentration of acylsilane B in the mixed solution is between 0.1 M and 1 M.

5. The method for synthesizing a furan compound according to any one of claims 1 - 3, characterized in that: The said separation and purification include filtration, concentration, recrystallization and column chromatography.

Images