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Structure of 811-68-7 * Storage: {[proInfo.prStorage]}
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 16-17, p. 3521 - 3528
2
[ 75-15-0 ]
[ 811-68-7 ]
Yield
Reaction Conditions
Operation in experiment
76%
for 18 h; Darkness; Inert atmosphere; Reflux
AgF (1 eq, 47.4 mmol, 6 g), CS2 (2.1 eq, 99.3 mmol, 6 mL) in CH3CN(12 mL) were placed in a dark flask under N2 atmosfere and heated to reflux for 18 h. After this time, the mixture was cooled to RT and all the volatile parts were removed under reduced pressure. The remaining black residue was then dissolved in AcOEt, all the insoluble parts werere moved by filtration and the liquid phase was concentrated with the aid of a rotary evaporator. The resulting pale yellow solid was then dissolved in a small amount of CH3CN and 40 mL of Et2O were carefully layered on top of this solution. The mixture was then placed at −15 °Cfor 24 h to produce a needle-shaped white solid that was recovered by filtration and washed with cooled Et2O. The solid was stored at 5 °C with the exclusion of light. Yield: 0.62 g, 76percent. 19F NMR (CD3CN): δ−22.51 (s) ppm.
8 g
at 80℃; Inert atmosphere; Glovebox
(1) in the glove box 15g into tachiol in the drying reaction bottle, the bottle is covered with the glove box. In a nitrogen atmosphere by adding 80 ml of heavy evaporation of the acetonitrile and 25 ml carbon bisulfide, reflux condensation tube in fast filled 80 °C reflux overnight. Then the carbon bisulfide boil off, then the remaining rotary evaporimeter turns on lathe doesthe nitrile uses b to obtain black solid. Then with ethyl acetate and a black solid dissolve and wash using diatomaceous earth filter, and washing several times. Under lucifugal terms turns on lathe does the filtrate to obtain viscous solid, with 60 after viscous solid dissolving drop second grade nitrile, the 180 ml ethyl ether is slowly added along the bottle wall. This mixed liquid still at room temperature 12 hours later, the -20 ° C for 24 hours. turns on lathe does ethyl ether and to continue to throw a metal luster obtained gray solid tachiol 8 g
Reference：
[1] Angewandte Chemie, International Edition, 2014, vol. 53, # 35, p. 9316 - 9320,5[2] Angewandte Chemie, 2014, vol. 126, # 35, p. 9470 - 9474,5
[3] Organic Letters, 2015, vol. 17, # 12, p. 3011 - 3013
[4] Angewandte Chemie - International Edition, 2013, vol. 52, # 12, p. 3457 - 3460[5] Angew. Chem., 2013, vol. 125, # 12, p. 3541 - 3544,4
[6] Catalysis Today, 2018, vol. 308, p. 94 - 101
[7] Journal of the Chemical Society, [8] Journal of the Chemical Society, 1961, p. 2597 - 2599
[9] Journal of the Chemical Society, [10] Journal of the Chemical Society, 1961, p. 2597 - 2599
[11] , Gmelin Handbook: Ag: MVol.B7, 1.20.2.1.1, page 4 - 10,
[12] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.11, page 32 - 49,
[13] Chemistry - A European Journal, 2014, vol. 20, # 32, p. 9867 - 9870
[14] Angewandte Chemie - International Edition, 2015, vol. 54, # 13, p. 4070 - 4074[15] Angew. Chem., 2015,
[16] European Journal of Organic Chemistry, 2016, vol. 2016, # 6, p. 1091 - 1094
[17] Patent: CN105669503, 2016, A, . Location in patent: Page/Page column 5
3
[ 14104-20-2 ]
[ 2926-29-6 ]
[ 811-68-7 ]
Yield
Reaction Conditions
Operation in experiment
89%
With triphenylphosphine In acetonitrile at 0 - 50℃; for 12 h; Inert atmosphere
Under a nitrogen atmosphere, AgBF4 (19.77 g, 100 mmol) and CF3SO2Na (18.73 g, 120 mmol) were dissolved in anhydrous acetonitrile (400 mL). The reaction solution was cooled to 0°C followed by the addition of Ph3P (62.95 g, 240 mmol). The reaction solution was returned to room temperature. The reaction was heated to 50 ° C for 12 hours. After the reaction, the reaction solution was filtered through celite, and the filtrate was cooled to -20 °C. After sufficient precipitation of crystals, the supernatant was purged to remove most of the triphenylphosphine oxide. The supernatant was removed in vacuo to remove the solvent. The residue was washed thoroughly with ether, vacuum-dried, and the residual solid was recrystallized from tetrahydrofuran and benzene to obtain trifluoromethylthio silver (I) (18.60 g, yield 89percent).
With tri-tert-butyl phosphine In acetonitrile at 0 - 20℃; for 12 h; Inert atmosphere
Under a nitrogen atmosphere, AgOTf (25.69 g, 100 mmol) and CF3SO2Na (18.73 g, 120 mmol) was dissolved in anhydrous acetonitrile (400 mL), the reaction solution was cooled to 0°C followed by the addition of tBu3P (50.58 g,250 mmol). The reaction solution was returned to room temperature, and stirred well at room temperature for 12 hours. After the reaction, the reaction solution was filtered through celite, the filtrate was cooled to -20 ° C, and crystals were precipitated. The supernatant was purged to remove most of the tri-tert-butylphosphine oxide. The supernatant was removed in vacuo to remove the solvent. The residue was washed thoroughly with ether, vacuum-dried and the residual solid was recrystallized from tetrahydrofuran and toluene to give the product trifluoromethylthio silver(I) (17.55 g, yield 84percent).
With triphenylphosphine In acetonitrile at 0 - 80℃; for 12 h; Inert atmosphere
Under nitrogen atmosphere, AgF (12.69 g, 100 mmol) and CF3SO2Na (23.41 g, 150 mmol) was dissolved in anhydrous acetonitrile (400 mL). The reaction solution was cooled to 0 ° C, followed by the addition of Ph3P (83.94 g, 320 mmol). The reaction solution was returned to room temperature and heated to 80°C for 12 hours. After the reaction, the reaction solution was filtered through celite, the filtrate was cooled to -20 °C, and crystals were precipitated. The supernatant was purged to remove most of the triphenylphosphine oxide. The supernatant was removed in vacuo to remove the solvent. The residue was washed thoroughly with ether, vacuum-dried and the residual solid was recrystallized from acetonitrile and ether to give the product trifluoromethylthio silver (I) (14.00 g, yield 67percent).
With trimethylphosphane In acetonitrile at 0 - 50℃; for 10 h; Inert atmosphere
Under a nitrogen atmosphere, AgCl (14.33 g, 100 mmol) and CF3SO2Na (23.41 g, 150 mmol) was dissolved in anhydrous acetonitrile (500 mL). The reaction solution was cooled to 0 ° C, followed by the addition of Me3P (22.82 g, 300 mmol). The reaction solution was returned to room temperature and heated to 50°C for 10 hours. After the reaction, the reaction solution was filtered through celite, the filtrate was cooled to -20°C, crystals were precipitated, and the supernatant was purged to remove most of the trimethylphosphine oxide. The supernatant was removed in vacuo to remove the solvent. The residue was washed thoroughly with ether, vacuum-dried and the residual solid was recrystallized from acetonitrile and benzene to obtain trifluoromethylthio silver (I) (11.50 g, yield 55percent).
Under a nitrogen atmosphere, AgPF6 (25.28 g,100 mmol ) and CF3SO2Na (18.73 g,120 mmol) dissolved in anhydrous acetonitrile (400mL), the reaction solution was cooled to 0°C, followed by the addition of Ph3P (62.95 g, 240 mmol). The reaction solution was returned to room temperature and stirred at room temperature for 12 hours. After the reaction, the reaction solution was filtered through celite, the filtrate was cooled to -20 ° C, and crystals were precipitated. The supernatant was purged to remove most of the triphenylphosphine oxide. The supernatant was removed in vacuo to remove the solvent. The residue was washed thoroughly with ether, vacuum-dried and the residual solid was recrystallized from acetonitrile and toluene to give the product trifluoromethylthio silver (I)(17.97 g, yield 86percent).
Reference：
[1] Journal of the American Chemical Society, 1959, vol. 81, p. 3575
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 3575
[3] , Gmelin Handbook: Ag: MVol.B7, 1.20.2.1.1, page 4 - 10,
[4] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.11, page 32 - 49,
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1962, p. 1254 - 1260
[3] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.11, page 32 - 49,
12
[ 420-32-6 ]
[ 811-68-7 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1960, p. 3516 - 3520
[3] Journal of the Chemical Society, [4] Journal of the Chemical Society, 1962, p. 4361 - 4366
[5] , Gmelin Handbook: F: PerFHalOrg.1, 1.1.1.1, page 1 - 7,
13
[ 753-94-6 ]
[ 506-64-9 ]
[ 811-68-7 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1960, p. 3516 - 3520
[3] , Gmelin Handbook: Ag: MVol.B3, 16.4.1.7.5, page 305 - 307,
14
[ 563-63-3 ]
[ 21259-75-6 ]
[ 811-68-7 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1962, p. 1254 - 1260
[3] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.11, page 32 - 49,
15
[ 21259-75-6 ]
[ 811-68-7 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1962, p. 1254 - 1260
[3] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.11, page 32 - 49,
16
[ 2966-50-9 ]
[ 21259-75-6 ]
[ 811-68-7 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1962, p. 1254 - 1260
[3] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.11, page 32 - 49,
17
[ 21259-75-6 ]
[ 811-68-7 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1962, p. 1254 - 1260
[3] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.11, page 32 - 49,
18
[ 753-94-6 ]
[ 13966-57-9 ]
[ 811-68-7 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1960, p. 3516 - 3520
[3] , Gmelin Handbook: Ag: MVol.B7, 1.20.2.1.1, page 4 - 10,
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1960, p. 3516 - 3520
[3] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.10, page 27 - 31,
21
[ 330660-35-0 ]
[ 753-94-6 ]
[ 11128-24-8 ]
[ 420-32-6 ]
[ 1111-70-2 ]
[ 461-08-5 ]
[ 811-68-7 ]
Reference：
[1] Journal of the Chemical Society, [2] Journal of the Chemical Society, 1960, p. 3516 - 3520
[3] , Gmelin Handbook: F: PerFHalOrg.2, 1.1.6.10, page 27 - 31,
AgSCF3 (1.3 eq, 2.4 mmol, 500 mg) was added to a solution of <strong>[3481-09-2]N-chlorophthalimide</strong>(1 eq, 1.8 mmol, 330 mg) in CH3CN (8 mL) under N2 atmosphere. The mixture was stirred for 3 h at RT, then the solvent was removed by rotary evaporation. The crude obtained was dissolved in DCM, filtered through a celite pad and the solvent was removed by rotary evaporation to give a white solid. Yield: 0.40 g, 89%.1H NMR (300 MHz, CDCl3): delta 8.01 (dd, 2H, J = 6 Hz, J = 3 Hz),7.88 (dd, 2H, J =6 Hz, J = 3 Hz) ppm. 19F NMR (CDCl3): delta -49.32 (s,3F) ppm. 13C NMR (CDCl3): delta 165.7, 135.4, 131.4, 127.9 (q,J = 322.5 Hz), 124.7 ppm.
2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86%
In acetonitrile; at 20℃; for 0.166667h;
Saccharin (6.0 g) was reacted in methanol (120 ml) at room temperature for 5 minutes with tert-butyl hypochlorite (5 ml) to give the compoundChloro-saccharin 1a (6.0 g, 84%); Chloro-saccharin 1a (3.0 g) was reacted with trifluoromethylthio-silver (3.6 g) in acetonitrile (40 ml) at room temperature for 10 min to give Compound 1 (3.3 g, 86%). Reagent 1 is a white solid at room temperature, soluble in organic solvents such as dichloromethane, chloroform, acetone and acetonitrile.
86%
In acetonitrile; at 20℃; for 0.166667h;
Saccharin (6.0 g of) in methanol (120ml) at room temperature and tert-butyl hypochlorite (5ml) for 5 minutes to give saccharin chloro compound 1a (6.0g, 84%); chloro saccharin 1a (3.0g) and three difluoromethylthio-silver (3.6 g of) in acetonitrile (40ml) and reacted at room temperature for 10 minutes to give compound 1 (3.3g, 86%).Reagent 1 at room temperature a white solid was soluble in methylene chloride, chloroform, acetone, and acetonitrile.N - trifluoromethylthio-saccharin (2 - ((Trifluoromethyl) Thio) of benzo [D] isothiazol-3 (2H) -one1,1-dioxide)
86%
In acetonitrile; at 20℃; for 0.166667h;
Saccharin (6.0 g of) in methanol (120ml) and tert-butyl hypochlorite (5ml) for 5 minutes to give saccharin chloro compound 1a (6.0g, 84%) at room temperature; chloro saccharin 1a (3.0g) and three difluoromethylthio-silver (3.6 g of) the reaction at room temperature in acetonitrile (40ml) 10 minutes to give compound 1 (3.3g, 86%).
86%
In acetonitrile; at 20℃; for 0.166667h;Green chemistry;
Saccharin (6.0 g) was reacted with t-butyl hypochlorite (5 ml) in methanol (120 ml) for 5 minutes at room temperature to give the compound chlorosaccharide 1a (6.0 g, 84%);The chloro saccharin 1a (3.0 g) was reacted with trifluoromethylthio silver (3.6 g) in acetonitrile (40 ml) at room temperature for 10 minutes to give compound II (3.3 g, 86%).The compound II is a white solid at room temperature and is soluble in an organic solvent such as dichloromethane, chloroform, acetone or acetonitrile.
77%
In acetonitrile; at 20℃; for 0.166667h;Inert atmosphere;
<strong>[14070-51-0]N-chlorosaccharin</strong> (1 eq, 1.15 mmol, 250 mg) and AgSCF3 (1.2 eq,1.38 mmol, 288 mg) were dissolved in CH3CN (4 mL) under N2 atmosphere.The mixture was stirred vigorously at room temperature for 10 min. The CH3CN was then drained under reduced pressure. And the residue was extracted with CH2Cl2 (3 mL× 3). The solution wa scombined and the solvent was evaporated under vacuum. The residue was further dried under high vacuum to give compound 2b as a white solid. Yield 251 mg, 77%. 1H NMR (300 MHz, CDCl3): 8.20 (d, 1HJ = 7.5 Hz), 8.08-7.99 (m, 2H), 7.98-7.91 (m, 1H). 19F-NMR (CDCl3): delta -47.73 (s, 3F) ppm. 13C NMR (CDCl3): 158.4,137.9, 136.4, 135.0, 127.8 (q, J = 315 Hz), 126.5, 126.1, 122.0 ppm.
3-methyl-3-((trifluoromethyl)thio)butyl benzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
51%
With 2,6-dimethylpyridine; ammonium peroxydisulfate; In acetonitrile; at 90℃; for 2h;Inert atmosphere;
Trifluoromethylthio silver (0.5 mmol), 2,6-lutidine (0.1 mmol) and ammonium persulfate (1.0 mmol) were added to the reaction flask, and after evacuating the argon three times, <strong>[94-46-2]isoamyl benzoate</strong> 1.0 mmol) and acetonitrile (5 mL). The reaction flask was placed in an oil bath at 90 C start heating and stirring 2h removed, to be cooled to room temperature. Using trifluoromethylbenzene as an internal standard substance, it was confirmed by 19F-NMR that 3-methyl-3-trifluoromethylthiobutyl benzoate was formed (a yield of 63%). The reaction mixture was filtered and the filtrate was evaporated to remove the solvent by a rotary evaporator. The residue was separated by column chromatography and concentrated under reduced pressure to give a colorless oil (75 mg, yield 51%).
2-chloro-3-trifluoromethylthio-1,4-naphthoquinone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
With dipotassium peroxodisulfate; Cu2(OH)2CO3·H2O; In acetonitrile; at 65℃;Schlenk technique; Inert atmosphere;
General procedure: Procedure A: A 25 mL Schlenk tube equipped with a magnetic stirbar was charged with quinones (0.2 mmol, 1.0 equiv), Cu2(OH)2CO3·H2O(71.7 mg, 0.3 mmol, 1.5 equiv), AgSCF3 (125.3mg, 0.6 mmol, 3.0 equiv), K2S2O8 (162.2mg, 0.6 mmol, 3.0 equiv). The tube was sealed with a septum, evacuated, andbackfilled with nitrogen three times. Then CH3CN (1.0 mL) was addedby a syringe. The mixture was stirred at 65 oCovernight. 5 mL saturated ammonium chloride aqueous solution was added. Theresulting mixture was filtered by Celite, eluted with diethyl ether. Separatedthe layers and the water phase was extracted with diethyl ether. The combinedorganic phase was washed with brine, dried over Na2SO4,filtered, and concentrated under reduced vacuum. The residue was purified withsilica gel column chromatography to provide the pure product.
2-bromo-3-trifluoromethylthio-1,4-naphthoquinone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
With dipotassium peroxodisulfate; Cu2(OH)2CO3·H2O; In acetonitrile; at 65℃;Schlenk technique; Inert atmosphere;
General procedure: Procedure A: A 25 mL Schlenk tube equipped with a magnetic stirbar was charged with quinones (0.2 mmol, 1.0 equiv), Cu2(OH)2CO3·H2O(71.7 mg, 0.3 mmol, 1.5 equiv), AgSCF3 (125.3mg, 0.6 mmol, 3.0 equiv), K2S2O8 (162.2mg, 0.6 mmol, 3.0 equiv). The tube was sealed with a septum, evacuated, andbackfilled with nitrogen three times. Then CH3CN (1.0 mL) was addedby a syringe. The mixture was stirred at 65 oCovernight. 5 mL saturated ammonium chloride aqueous solution was added. Theresulting mixture was filtered by Celite, eluted with diethyl ether. Separatedthe layers and the water phase was extracted with diethyl ether. The combinedorganic phase was washed with brine, dried over Na2SO4,filtered, and concentrated under reduced vacuum. The residue was purified withsilica gel column chromatography to provide the pure product.
With dipotassium peroxodisulfate; iodine; potassium iodide; In acetonitrile; at 60℃; for 24h;Schlenk technique;
General procedure: N-benzyl-indole 1 (0.1 mmol), AgSCF3 (31.4 mg, 0.15 mmol), KI (24.9 mg, 0.15 mmol), I2 (63.5 mg, 0.25 mmol), and K2S2O8 (81.1 mg, 0.3 mmol) were combined in an oven-dried Schlenk tube, and CH3CN (3 mL) was added via syringe. After stirring at 60 C for 24 h, the reaction mixture was then cooled to room temperature, filtered through a plug of silica and washed with EtOAc. Removal of the solvent in vacuo and purification of the residue by flash column chromatography on silica gel (petroleum ether : EtOAc = 50:1) to afford the desired product 2.
(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-4-((trifluoromethyl)thio)but an-2-yl)decahydro-1H-cyclopenta[a]phenanthrene-3,7,12(2H,4H,8H)-trione[ No CAS ]
In acetonitrile; at 0 - 20℃; for 12h;Inert atmosphere;
Under a nitrogen atmosphere, <strong>[26042-63-7]AgPF6</strong> (25.28 g,100 mmol ) and CF3SO2Na (18.73 g,120 mmol) dissolved in anhydrous acetonitrile (400mL), the reaction solution was cooled to 0C, followed by the addition of Ph3P (62.95 g, 240 mmol). The reaction solution was returned to room temperature and stirred at room temperature for 12 hours. After the reaction, the reaction solution was filtered through celite, the filtrate was cooled to -20 C, and crystals were precipitated. The supernatant was purged to remove most of the triphenylphosphine oxide. The supernatant was removed in vacuo to remove the solvent. The residue was washed thoroughly with ether, vacuum-dried and the residual solid was recrystallized from acetonitrile and toluene to give the product trifluoromethylthio silver (I)(17.97 g, yield 86%).
According to the literature (Kang, K.; Xu, C.; Shen, Q. Organic Chemistry Frontiers 2014, 7, 294.), using AgSCF3 (silver trifluoromethanethiolate) and <strong>[2439-85-2]N-bromophthalimide</strong> (<strong>[2439-85-2]N-bromophthalimide</strong>) in anhydrous acetonitrile, After reacting for 3 h under argon, the excess acetonitrile was evaporated by a rotary evaporator, dissolved in 15 mL of dichloromethane, filtered, and the filtrate was removed to remove methylene chloride to give a white solid (N-trifluoromethylthio)phthalimide).
With potassium bromide; In acetonitrile; at 25℃; for 12h;
General procedure: Potassium fluoride (3 mmol), sulfur (4 mmol), 10 mL of tetrahydrofuran and trifluoromethyltrimethylsilane (5 mmol) were added under nitrogen, Then, N-methylaniline (1 mmol) in (10 ml) dissolved in tetrahydrofuran was added dropwise to the reaction system, and the reaction system was stirred at room temperature for 1 hour, and the solvent was removed under reduced pressure to give a crude product, the structure as shown in formula (2-1). The crude product was subjected to column chromatography (ethyl acetate: petroleum ether = 1 : 100) to give a pure product. Yield is 92%. (1. The same conditions as above, when the solvent is DMF, the yield is 50%; 2. In the same condition, when the sulfur is 8 equivalents, the yield is 91%; 3. The same conditions, when the potassium fluoride is 6 equivalents, the yield is 90%; 4. Same as above, when trifluoromethyltrimethylsilane, the yield is 91%) Method 2: N-methylaniline (0.2 mmol) was dissolved in acetonitrile (2 mL), KBr (0.3mmol), AgSCF3 (0.3 mmol) was added to acetonitrile (2 mL), and then the nitrogen methyl aniline dissolved in acetonitrile (2.0 ml) was added dropwise to the reaction system, and the reaction system was added at 25 C. Stir for 1 hour, The solvent was removed under reduced pressure to give the crude product, the structure as shown in formula (2-1). The crude product was subjected to column chromatography (ethyl acetate: petroleum ether = 1:1) to give a pure product.The yield was 83% (1. the same as above, when the potassium bromide was 3 equivalents, the silver trifluoromethane was 3 equivalents, and the yield was 82%)
4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-carbothioyl fluoride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
With potassium bromide; In acetonitrile; at 25℃; for 1.0h;
General procedure: Potassium fluoride (3 mmol), sulfur (4 mmol), 10 mL of tetrahydrofuran and trifluoromethyltrimethylsilane (5 mmol) were added under nitrogen, Then, N-methylaniline (1 mmol) in (10 ml) dissolved in tetrahydrofuran was added dropwise to the reaction system, and the reaction system was stirred at room temperature for 1 hour, and the solvent was removed under reduced pressure to give a crude product, the structure as shown in formula (2-1). The crude product was subjected to column chromatography (ethyl acetate: petroleum ether = 1 : 100) to give a pure product. Yield is 92%. (1. The same conditions as above, when the solvent is DMF, the yield is 50%; 2. In the same condition, when the sulfur is 8 equivalents, the yield is 91%; 3. The same conditions, when the potassium fluoride is 6 equivalents, the yield is 90%; 4. Same as above, when trifluoromethyltrimethylsilane, the yield is 91%) Method 2: N-methylaniline (0.2 mmol) was dissolved in acetonitrile (2 mL), KBr (0.3mmol), AgSCF3 (0.3 mmol) was added to acetonitrile (2 mL), and then the nitrogen methyl aniline dissolved in acetonitrile (2.0 ml) was added dropwise to the reaction system, and the reaction system was added at 25 C. Stir for 1 hour, The solvent was removed under reduced pressure to give the crude product, the structure as shown in formula (2-1). The crude product was subjected to column chromatography (ethyl acetate: petroleum ether = 1:1) to give a pure product.The yield was 83% (1. the same as above, when the potassium bromide was 3 equivalents, the silver trifluoromethane was 3 equivalents, and the yield was 82%)
With copper(l) iodide; potassium carbonate; In acetonitrile; at 20℃; for 12h;
General procedure: In an oven-dried 25 mL plug tube equipped with a stir bar were added arenediazonium salts 1a-w (0.5 mmol), AgSCF3 (156 mg, 0.75 mmol), CuI (95 mg, 0.5 mmol), K2CO3 (138 mg, 1.0 mmol). 5 ml of acetonitrile without further purification was added. The reaction mixture was stirred at room temperature for 12 h. After the reaction, the reaction mixture was diluted with dichloromethane (DCM), filtered through a plug of celite and washed with dichloromethane. The reaction mixture was extracted with DCM (3×10 mL). The combined organic layer was washed with brine (30 mL) and dried over anhydrous Na2SO4, then concentrated under vacuum and purified by silica gel flash column chromatography using hexane as eluent.
With copper(l) iodide; potassium carbonate In acetonitrile at 20℃; for 12h;
Copper-Promoted Triuoromethylthiolation of Arenediazonium salts with AgSCF3
General procedure: In an oven-dried 25 mL plug tube equipped with a stir bar were added arenediazonium salts 1a-w (0.5 mmol), AgSCF3 (156 mg, 0.75 mmol), CuI (95 mg, 0.5 mmol), K2CO3 (138 mg, 1.0 mmol). 5 ml of acetonitrile without further purification was added. The reaction mixture was stirred at room temperature for 12 h. After the reaction, the reaction mixture was diluted with dichloromethane (DCM), filtered through a plug of celite and washed with dichloromethane. The reaction mixture was extracted with DCM (3×10 mL). The combined organic layer was washed with brine (30 mL) and dried over anhydrous Na2SO4, then concentrated under vacuum and purified by silica gel flash column chromatography using hexane as eluent.
6-methoxy-2-(trifluoromethylthio)quinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
54%
With p-toluenesulfonylanhydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20℃; for 4h;Schlenk technique;
General procedure: A mixture of heteroaryl N-oxide (0.4mmol), AgSCF3 (166.3mg, 0.8mmol), Ts2O (195.8mg, 0.6mmol), and n-Bu4NI (295.5mg, 0.8mmol) was added in a 25mL Schlenk tube, and then THF (4.0mL) was added. The mixture was stirred at room temperature for 4h. After the reaction was complete, saturated NH4Cl solution was added. The resulting mixture was extracted with EtOAc for three times. The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EA=100:1) to give the desired product (2a-2w).f
4-bromo-1-(trifluoromethylthio)isoquinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
71%
With p-toluenesulfonylanhydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20℃; for 4.0h;Schlenk technique;
General procedure: A mixture of heteroaryl N-oxide (0.4mmol), AgSCF3 (166.3mg, 0.8mmol), Ts2O (195.8mg, 0.6mmol), and n-Bu4NI (295.5mg, 0.8mmol) was added in a 25mL Schlenk tube, and then THF (4.0mL) was added. The mixture was stirred at room temperature for 4h. After the reaction was complete, saturated NH4Cl solution was added. The resulting mixture was extracted with EtOAc for three times. The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EA=100:1) to give the desired product (2a-2w).f
4-phenyl-2-(trifluoromethylthio)pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
26%
With p-toluenesulfonylanhydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20℃; for 4h;Schlenk technique;
General procedure: A mixture of heteroaryl N-oxide (0.4mmol), AgSCF3 (166.3mg, 0.8mmol), Ts2O (195.8mg, 0.6mmol), and n-Bu4NI (295.5mg, 0.8mmol) was added in a 25mL Schlenk tube, and then THF (4.0mL) was added. The mixture was stirred at room temperature for 4h. After the reaction was complete, saturated NH4Cl solution was added. The resulting mixture was extracted with EtOAc for three times. The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EA=100:1) to give the desired product (2a-2w).f
With dipotassium peroxodisulfate; oxygen In dimethyl sulfoxide at 35℃; for 3h; Schlenk technique;
General Procedure for oxidative trifluoromethylthiolation of alkenes is as follows:
General procedure: In an oven-dried 25 mL Schlenk tube equipped with a stir bar were added alkenes 1 (0.5 mmol),AgSCF3 (0.75 mmol, 1.5 equiv.) and K2S2O8 (1.0 mmol, 2.0 equiv). The Schlenk tube was evacuated andrefilled with oxygen balloon. DMSO (5 mL) was then added by syringe. The reaction mixture was stirred for3 h at 35 oC. After cooling to room temperature, the reaction mixture was diluted with dichloromethane,filtered through a plug of celite and washed with dichloromethane. The reaction mixture was extracted withDCM (3×10 mL). The combined organic layer was washed with brine (30 mL) and dried over anhydrousNa2SO4, then concentrated under vacuum and purified by silica gel flash column chromatography usingpetroleum ether (60-90 oC)/ethyl acetate as eluent.
1-(2-nitrophenyl)-2-((trifluoromethyl)thio)ethanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
57%
With dipotassium peroxodisulfate; oxygen In dimethyl sulfoxide at 35℃; for 3h; Schlenk technique;
General Procedure for oxidative trifluoromethylthiolation of alkenes is as follows:
General procedure: In an oven-dried 25 mL Schlenk tube equipped with a stir bar were added alkenes 1 (0.5 mmol),AgSCF3 (0.75 mmol, 1.5 equiv.) and K2S2O8 (1.0 mmol, 2.0 equiv). The Schlenk tube was evacuated andrefilled with oxygen balloon. DMSO (5 mL) was then added by syringe. The reaction mixture was stirred for3 h at 35 oC. After cooling to room temperature, the reaction mixture was diluted with dichloromethane,filtered through a plug of celite and washed with dichloromethane. The reaction mixture was extracted withDCM (3×10 mL). The combined organic layer was washed with brine (30 mL) and dried over anhydrousNa2SO4, then concentrated under vacuum and purified by silica gel flash column chromatography usingpetroleum ether (60-90 oC)/ethyl acetate as eluent.
Chemistry
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Inhibitors/Agonists
Material Science
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