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CAS No. : | 58109-40-3 | MDL No. : | MFCD00061398 |
Formula : | C12H10F6IP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DSSRLRJACJENEU-UHFFFAOYSA-N |
M.W : | 426.08 | Pubchem ID : | 2737136 |
Synonyms : |
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Signal Word: | Danger | Class: | 8,6.1 |
Precautionary Statements: | P280-P301+P310-P305+P351+P338-P310 | UN#: | 2923 |
Hazard Statements: | H301-H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(II) benzoate In chlorobenzene at 125℃; Inert atmosphere; Microwave irradiation; Darkness; | |
77% | In chlorobenzene at 125℃; for 0.2h; Inert atmosphere; | 1 In a 2 mL glass reaction vessel, purchased from CEM Corporation, microwave reactor manufacturer (heavy walled vessels with corresponding septum designed to withstand up to 3000 psi inside the reaction chamber), 0.21 g (0.24 mmol) of 5, 0.21 g (0.48 mmol) of diphenyliodonium hexafluoro phosphate (V), 6, and 0.006 g (5% molar) copper(II) benzoate were mixed in the dark in 2 mL of chlorobenzene while being purged with N2. The microwave was set to closed vessel standard mode; maximum pressure 40 psi; maximum temperature 125° C., maximum power 100 W, high speed stirring. The run time (time at which the reaction reaches max temperature or pressure) was set for 30 s and the hold time for 1 min. The reaction was monitored by thin layer chromotography (TLC) until most of the starting material had disappeared. Rarely did sulfides convert entirely. In the cases in which the reaction time was extended to try to achieve full conversion, side products seriously complicated the purification hindering the overall yield of the sulfonium salt.Upon completion, 12 min hold time, the solvent was vacuum distilled affording a dark yellow crude. 1H NMR revealed the presence of what appeared to mono-(45%) and bis-sulfonium (55%). The derivatives which were separated by column chromatography using hexane:ethyl acetate 6:4 as eluent, the faster eluting fraction (likely the mono-sulfonium) quickly decomposed and wasn't characterized. The second fraction was a dark yellow solid (0.239 g, 77%): Mp 63.5-65.8° C.; 1H NMR (500 MHz, acetone-d6) 8.08 (d, 10 Hz, 4H), 7.93 (m, 28H), 7.70 (m, 4H), 7.53 (d, 20 Hz, 2H), 2.15 (m, 4H), 1.14 (m, 28H), 0.78 (t, 5 Hz, 6H), 0.65 (m, 4H). 13C NMR (125 MHz, acetone-d6) 151.8 (C), 144.4 (C), 141.7 (C), 136.0 (C), 134.7 (CH), 134.5 (C), 131.9 (CH), 131.6 (CH), 131.2 (CH), 129.0 (CH), 126.9 (C), 125.5 (C), 125.3 (CH), 121.8 (C), 120.5 (C), 120.4 (C), 55.1 (C), 40.0 (C), 31.7 (C), 23.6 (C), 22.3 (C), 13.5 (C). Elemental Analysis Calcd. for (C73H80F12P2S2): C, 66.85; H, 6.15; S, 4.89. Found: C, 66.94; H, 6.28; S, 4.69. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With copper(II) benzoate In chlorobenzene at 125℃; Inert atmosphere; Microwave irradiation; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(II) benzoate In chlorobenzene at 125℃; Inert atmosphere; Microwave irradiation; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With copper(II) benzoate In chlorobenzene at 125℃; for 0.0333333h; Inert atmosphere; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With palladium diacetate; sodium hydrogencarbonate In acetonitrile at 50℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate at 20℃; for 16h; Inert atmosphere; Irradiation; | Method A: Photoreaction of diaryliodonium salts with benzene or heteroarenes in the presence of 1 (entry 5, Table 1) In an oven-dried 10 mL round-bottom flask equipped with a magnetic stirrer bar, Ph2IPF6 (2,130 mg, 0.30 mmol), Ir(ppy)2bpyPF6 (1, 2.4 mg, 3.0 mol), 1-methylpyrrole (1.0 mL) were placed. The mixture was degassed by freeze-pump-thaw cycles and filled with nitrogen. The flask was placed 3 cm above 14W white LED (λ = 400-750 nm) and illuminated for 16 h. The mixture was evaporated, and the residue was purified by silica gel column chromatography with EtOAc/hexane (1/20) to give 1-methyl-2-phenyl-1H-pyrrole (41 mg, 88% yield) as a pale yellow solid. |
84% | With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 25℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In 1,2-dichloro-ethane at 120℃; for 48h; Schlenk technique; | 4.3. General procedure for the synthesis of the salts 7a-d General procedure: The pyridine-N-oxides 6a-d and diphenyliodonium hexafluorophosphate(V) were dried in vacuo in a Schlenk tube over a period of 1 h. Then, 8 mL of dichloroethane were added under an inert atmosphere, and the mixture was heated at 120°C for 48 h. After cooling to rt, 5 mL of methanol were added, the mixture was poured into a round flask and treated with 1 g of silica gel. Flash column chromatography was performed with a mixture of dichloromethane, petroleum ether, and methanol (10:5:3). |
8% | In 1,2-dichloro-ethane at 120℃; for 48h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | In 1,2-dichloro-ethane at 120℃; for 48h; Schlenk technique; | 4.3. General procedure for the synthesis of the salts 7a-d General procedure: The pyridine-N-oxides 6a-d and diphenyliodonium hexafluorophosphate(V) were dried in vacuo in a Schlenk tube over a period of 1 h. Then, 8 mL of dichloroethane were added under an inert atmosphere, and the mixture was heated at 120°C for 48 h. After cooling to rt, 5 mL of methanol were added, the mixture was poured into a round flask and treated with 1 g of silica gel. Flash column chromatography was performed with a mixture of dichloromethane, petroleum ether, and methanol (10:5:3). 4.3.1. 1-(2-Hydroxyphenyl)-pyridinium hexafluorophosphate 7a A sample of 0.380 g (4.00 mmol) of pyridine-N-oxide 6a and of 1.704 g (4.00 mmol) of diphenyliodonium hexafluorophosphate(V)was used. The salt 7a was obtained as red solid. Yield: 0.554 g (44%) ,mp. 62° C. 1H NMR (600 MHz, acetonitrile-d3): δ 8.83 (dd,J 6.8 Hz, J 1.4 Hz, 2 H, 2/6-H), 8.52 (tt, J 7.8 Hz, J 1.4 Hz,1 H, 4-H), 8.06 (dd, J 6.8 Hz, J 7.8 Hz, 2 H, 3/5-H), 7.33 (dd,J 7.7 Hz, J 1.7 Hz, 1 H, 60-H), 7.30 (ddd, J 8.8 Hz, J 7.8 Hz,J 1.7 Hz,1 H, 40-H), 7.03 (dd, J 7.8 Hz, J 1.3 Hz,1 H, 30-H), 6.75(ddd, J 8.8 Hz, J 7.7 Hz, J 1.3 Hz, 1 H, 50-H) ppm [1].3C NMR(150 MHz, acetonitrile-d): δ 157.2, 146.9, 146.4, 133.5, 132.2,128.4, 126.3, 120.4, 116.5 ppm. IR (ATR): ν=3129, 3067, 2926, 1469,1455, 829, 750, 677 cm1. ESIMS (100 V, ): m/z (%) 172.0 (100)[M]. HRESIMS: C11H10NO: required 172.0762. Found: 172.0764. |
17% | In 1,2-dichloro-ethane at 120℃; for 48h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(II) bis(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 120℃;Inert atmosphere; | The specific process: the 2 mmol (millimoles) Ph2IPF6, 2mmol thiophene carbonitrile and 0.4mmolCu (OTf)2Dissolved in 1, 2 - dichloroethane, N2(Nitrogen) atmosphere 120 C heating reflux 2h (hours), subsequently, cooling to room temperature, continue adding 2 times equivalent (i.e. 4mmol) thiophene carbonitrile, 120 C heating reflux 12h, beam after the reaction, the reaction liquid-cooled to the room temperature, adding anhydrous K2CO3, Dichloromethane is used for extracting the organic phase, anhydrous Na2SO4Drying the organic phase, filter, evaporate the solvent, column chromatography separation, to get the yellow solid, yield 60%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In ethyl acetate at 20℃; for 1h; | 3 Ionic Compound Synthesis Example 3 Potassium tris(trifluoromethanesulfonyl)methide (0.57 g, 1.34 mmol) was introduced into a pear-shaped flask, and the compound was dissolved in ethyl acetate (10 mL). An ethyl acetate solution (10 mL) of diphenyliodonium hexafluorophosphate (0.60 g, 1.33 mmol) was slowly added dropwise to the solution, and the mixture was stirred for one hour at room temperature. The organic layer was thoroughly washed with water, and then the solvent was distilled off. Thus, 0.90 g of a target ionic compound C was obtained as a white powder. Yield: 97.0%. The reaction scheme of this Synthesis Example is shown below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate In ethanol at 20℃; for 16h; Inert atmosphere; Irradiation; | Method A: Photoreaction of diaryliodonium salts with benzene or heteroarenes in the presence of 1 (entry 5, Table 1) General procedure: In an oven-dried 10 mL round-bottom flask equipped with a magnetic stirrer bar, Ph2IPF6 (2,130 mg, 0.30 mmol), Ir(ppy)2bpyPF6 (1, 2.4 mg, 3.0 mol), 1-methylpyrrole (1.0 mL) were placed. The mixture was degassed by freeze-pump-thaw cycles and filled with nitrogen. The flask was placed 3 cm above 14W white LED (λ = 400-750 nm) and illuminated for 16 h. The mixture was evaporated, and the residue was purified by silica gel column chromatography with EtOAc/hexane (1/20) to give 1-methyl-2-phenyl-1H-pyrrole (41 mg, 88% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate In acetonitrile at 20℃; for 16h; Inert atmosphere; Irradiation; | Method A: Photoreaction of diaryliodonium salts with benzene or heteroarenes in the presence of 1 (entry 5, Table 1) General procedure: In an oven-dried 10 mL round-bottom flask equipped with a magnetic stirrer bar, Ph2IPF6 (2,130 mg, 0.30 mmol), Ir(ppy)2bpyPF6 (1, 2.4 mg, 3.0 mol), 1-methylpyrrole (1.0 mL) were placed. The mixture was degassed by freeze-pump-thaw cycles and filled with nitrogen. The flask was placed 3 cm above 14W white LED (λ = 400-750 nm) and illuminated for 16 h. The mixture was evaporated, and the residue was purified by silica gel column chromatography with EtOAc/hexane (1/20) to give 1-methyl-2-phenyl-1H-pyrrole (41 mg, 88% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; at 20℃; for 16h;Inert atmosphere; Irradiation; | General procedure: In an oven-dried 10 mL round-bottom flask equipped with a magnetic stirrer bar, Ph2IPF6 (2,130 mg, 0.30 mmol), Ir(ppy)2bpyPF6 (1, 2.4 mg, 3.0 mol), 1-methylpyrrole (1.0 mL) were placed. The mixture was degassed by freeze-pump-thaw cycles and filled with nitrogen. The flask was placed 3 cm above 14W white LED (lambda = 400-750 nm) and illuminated for 16 h. The mixture was evaporated, and the residue was purified by silica gel column chromatography with EtOAc/hexane (1/20) to give 1-methyl-2-phenyl-1H-pyrrole (41 mg, 88% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate at 20℃; for 16h; Inert atmosphere; Irradiation; | Method A: Photoreaction of diaryliodonium salts with benzene or heteroarenes in the presence of 1 (entry 5, Table 1) General procedure: In an oven-dried 10 mL round-bottom flask equipped with a magnetic stirrer bar, Ph2IPF6 (2,130 mg, 0.30 mmol), Ir(ppy)2bpyPF6 (1, 2.4 mg, 3.0 mol), 1-methylpyrrole (1.0 mL) were placed. The mixture was degassed by freeze-pump-thaw cycles and filled with nitrogen. The flask was placed 3 cm above 14W white LED (λ = 400-750 nm) and illuminated for 16 h. The mixture was evaporated, and the residue was purified by silica gel column chromatography with EtOAc/hexane (1/20) to give 1-methyl-2-phenyl-1H-pyrrole (41 mg, 88% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; Schlenk technique; | |
86% | In N,N-dimethyl-formamide at 90℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With copper(I) bromide In acetonitrile at 80℃; for 2h; | General Procedure for Halogenation Reaction ofDiaryliodonium Salts with Cuprous Halide General procedure: A mixture of diaryliodonium salt (0.5 mmol), cuproushalide (0.75 mmol) and CH3CN (1mL) was taken in a 10mL reaction tube and heated at 80°C temperature for 2 hoursunder vigorous stirring. After completion of the reaction(observed on TLC or GC) the reaction mass was cooled toroom temperature, and 5 ml of water was added. The mixturewas stirred for 10 mins, the product was extracted with ethylacetate (3 * 10mL). The organic layer was washed withwater and dried over anhydrous sodium sulphate. Solventwas evaporated under reduced pressure to obtain the product.The crude product was purified on silica gel column by usingpetroleum ether and ethyl acetate as solvents to obtain thepure product. The obtained product was analyzed by 1HNMR, 13C NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium fluoride In N,N-dimethyl-formamide at 60℃; for 3h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: 1-acetyl-2,3-dihydro-1H-indol-3-one With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.25h; Schlenk technique; Stage #2: diphenyliodonium hexafluorophosphate In tetrahydrofuran at 30℃; for 10h; Schlenk technique; | general procedure for the synthesis of 3aa-3ao General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30°C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 6h; Schlenk technique; Sealed tube; regioselective reaction; | General procedure for the synthesis of 3a-j General procedure: 1a (72.1 mg, 0.5 mmol, 1 equiv), Cu(OTf)2 (18.1 mg, 0.05 mmol, 10 mol %), and 2 (0.6 mmol, 1.2 equiv) were added to Schlenk tube, sealed with a rubber under air. Then 2 mL DCE was added using a syringe. The reaction mixture was stirred at 80°C for 6 h. After cooling to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel using a proper eluent to afford the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: 2-(phenylthio)thioxanthone; diphenyliodonium hexafluorophosphate With copper(II) benzoate In chlorobenzene at 120 - 125℃; for 3h; Stage #2: potassium tris(pentafluoroethyl)trifluorophosphate In dichloromethane; water at 25℃; for 2h; | 2 Synthesis of diphenyl-2-thioxanthonylsulfonium tris (pentafluoroethyl) trifluorophosphate (RS 2-FP) 15.0 parts of 2- (phenylthio) thioxanthone,41.9 parts of diphenyliodonium hexafluorophosphate,0.4 parts of copper (II) benzoate and 300 parts of chlorobenzene were uniformly mixed,After reacting at 120 to 125 ° C. for 3 hours,The reaction solution was cooled to room temperature (about 25 ° C.)It was charged into 300 parts of distilled water,The product was precipitated.This was filtered,The residue was washed with water until the pH of the filtrate became neutral,After drying the residue under reduced pressure,100 parts of diethyl ether was added, the mixture was dispersed in diethyl ether by an ultrasonic washing machine, allowed to stand for about 15 minutes, and the operation of removing the supernatant was repeated three times,The generated solid was washed.Then,The solid was transferred to a rotary evaporator,By distilling off the solvent,A yellow solid was obtained.This yellow solid was dissolved in 770 parts of dichloromethane,After throwing into 342 parts of 10% tris (pentafluoroethyl) potassium trifluorophosphate aqueous solution,The mixture was stirred at room temperature (about 25 ° C.) for 2 hours,The organic layer was washed several times with water,By drying under reduced pressure,Diphenyl-2-thioxanthonylsulfonium tris (pentafluoroethyl) trifluorophosphate was obtained in a yield of 98%. |
Stage #1: 2-(phenylthio)thioxanthone; diphenyliodonium hexafluorophosphate With copper(II) benzoate In chlorobenzene at 120 - 125℃; for 3h; Stage #2: potassium tris(pentafluoroethyl)trifluorophosphate In dichloromethane; water at 25℃; for 2h; | 2 Synthesis of diphenyl-2-thioxanthonylsulfonium tris(pentafluoroethyl)trifluorophosphate (RS2-FP) 2- (phenylthio) thioxanthone15.0 parts, 41.9 parts of diphenyliodonium hexafluorophosphate, 0.4 parts of copper benzoate (II) and chlorobenzene 300 parts were uniformly mixed and allowed to react for 3 hours at 120 ~ 125 , room temperature the reaction solution (about 25 ) until cooled, poured into 300 parts of distilled water, to precipitate the product. This was filtered, the residue was washed until the pH of the filtrate became neutral with water, after which the residue was dried under reduced pressure, adding 100 parts of diethyl ether was dispersed in diethyl ether using an ultrasonic washing machine for about 15 minutes static and repeated three times to remove the supernatant after location, washed resulting solid. Then, it transferred the solid in a rotary evaporator and evaporated to give a yellow solid. Dissolve the yellow solid in 770 parts of dichloromethane, after turning in 10% aqueous solution of potassium tris (pentafluoroethyl) trifluorophosphate 342 parts, stirred for 2 hours at room temperature (about 25 ° C.), a few times and the organic layer with water washed, and dried under reduced pressure, the diphenyl-2-thioxanthonylsulfonium sulfonyl sulfonium tris (pentafluoroethyl) trifluoro phosphate was obtained in a yield of 98%. | |
Stage #1: 2-(phenylthio)thioxanthone; diphenyliodonium hexafluorophosphate With copper(II) benzoate In chlorobenzene at 120 - 125℃; for 3h; Stage #2: potassium tris(pentafluoroethyl)trifluorophosphate In dichloromethane; water at 25℃; for 2h; | 2 Synthesis of diphenyl-2-thioxanthonylsulfonium tris (pentafluoroethyl) trifluorophosphate (H-2) 15.0 parts of 2- (phenylthio) thioxanthone, 41.9 parts of diphenyliodonium hexafluorophosphate, 0.4 part of copper (II) benzoate and 300 parts of chlorobenzene were mixed uniformly and reacted at 120 to 125 ° C. for 3 hours After that, the reaction solution was cooled to room temperature (about 25 ° C.) and charged into 300 parts of distilled water to precipitate the product. This was filtered, the residue was washed with water until the pH of the filtrate became neutral, the residue was dried under reduced pressure, then 100 parts of diethyl ether was added and dispersed in diethyl ether by an ultrasonic washing machine and allowed to stand still The operation of removing the supernatant after the placement was repeated three times, and the produced solid was washed. The solid was then transferred to a rotary evaporator and the solvent was distilled off to give a yellow solid. This yellow solid was dissolved in 770 parts of dichloromethane and poured into 342 parts of a 10% aqueous solution of potassium tris (pentafluoroethyl) trifluorophosphate, stirred at 25 ° C. for 2 hours, the organic layer was washed several times with water, And dried to obtain diphenyl-2-thioxanthonylsulfonium tris (pentafluoroethyl) trifluorophosphate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With potassium <i>tert</i>-butylate In 1,2-dichloro-ethane at 60℃; for 0.5h; Schlenk technique; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 2-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline With potassium <i>tert</i>-butylate In acetonitrile at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: diphenyliodonium hexafluorophosphate In acetonitrile at 60℃; Schlenk technique; Inert atmosphere; regioselective reaction; | 6. Synthesis of 2-aryl-4-aryloxyquinolines (3a-u). General procedure C General procedure: Under an inert atmosphere in 10 mL round-bottom flask were added 2-Aryl-4-quinolone (1.00 equiv), potassium tert-butoxide (1.50 equiv) and acetonitrile (3 mL). Theround-bottom flask was then placed in a preheated oil bath at 60 °C. After 10 mindiaryliodonium salt (2.00 equiv) was added to the reaction mixture. The reaction mixture wascontinued stirring for 20-30 min until TLC showed completion of the reaction, solvent wasremoved and then added water (20 mL) to the reaction mixture and it was extracted with ethylacetate (2 × 10 mL). The organic phase was separated, washed with brine (2 × 15 mL), driedover anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product thus obtainedwas purified by silica gel (100-200) column chromatography to afford the purearyloxyquinoline. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In 1,2-dichloro-ethane; at 20 - 120℃; for 48h;Inert atmosphere; | To a 25 mL sealed tube,Join2-amino-4-methylbenzonitrile(2.0 mmol, 236 mg),Diphenyl high iodine hexafluorophosphate (1.0 mmol, 426 mg)After purging nitrogen three times,1,2-dichloroethane (3 mL) was added.The system was stirred at room temperature for 15-30 minutes,So that the system mix evenly,The tube was transferred to an oil bath at 120 C for 2 days.After the reaction,The system is cooled to room temperature.To the system by adding 3mL of methanol,Potassium carbonate (1 mmol, 138 mg), 2 drops of deionized water,Stir at room temperature for 3-5 h.System liquid concentrated spin dry to get crude products.The crude product was chromatographed on ethyl acetate: petroleum ether: triethylamine = 5: 3: 1 as eluent(200-300 mesh silica gel) to give a white solid product with a purity of greater than 99%Preparation of 2- (4-imino-7-methyl-3-phenyl-3,4-dihydroquinazoline) -5-methylaniline300.9 mg, the isolated yield was 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,2-dichloro-ethane; at 20 - 120℃; for 48h;Inert atmosphere; | To a 25 mL sealed tube,<strong>[61272-77-3]2-amino-5-fluoro-benzonitrile</strong> (2.0 mmol, 236 mg) was added,Diphenyl high iodine hexafluorophosphate (1.0 mmol, 426 mg)After purging nitrogen three times,1,2-dichloroethane (3 mL) was added.The system was stirred at room temperature for 15-30 minutes,So that the system mix evenly,The tube was transferred to an oil bath at 120 C for 2 days.After the reaction, the system was cooled to room temperature.To the system by adding 3mL of methanol,Potassium carbonate (1 mmol, 138 mg), 2 drops of deionized water,Stir at room temperature for 3-5 h.System liquid concentrated spin dry to get crude products.The crude product was chromatographed on ethyl acetate: petroleum ether: triethylamine = 5: 3: 1 as eluent(200-300 mesh silica gel) to give a gray solid product with a purity greater than 99%4-fluoro-2- (6-fluoro-4-imino-3-phenyl-3,4-dihydroquinazoline) -2-aniline. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In 1,2-dichloro-ethane at 20 - 120℃; for 48h; Inert atmosphere; | 1 Preparation of (2-(3-phenyl)-4-imino-3,4-dihydroquinazoline)-2-aniline To a 25 mL sealed tube,2-Aminobenzonitrile (2.0 mmol, 236 mg) was added,Diphenyl high iodine hexafluorophosphate (1.0 mmol, 426 mg)After purging nitrogen three times,Join1,2-dichloroethane(3 mL).The system was stirred at room temperature for 15-30 minutes,So that the system mix evenly,The tube was transferred to an oil bath at 120 ° C for 2 days.After the reaction, the system was cooled to room temperature.To the system by adding 3mL of methanol,Potassium carbonate (1 mmol, 138 mg), 2 drops of deionized water,Stir at room temperature for 3-5 h.System liquid concentrated spin dry to get crude products.The crude product was chromatographed on ethyl acetate: petroleum ether: triethylamine = 5: 3: 1 as eluant (200-300Head silica gel),To obtain a milky white solid product having a purity of more than 99%Preparation of 2- (3-phenyl) -4-imino-3,4-dihydroquinazoline) - 2-aniline 287.4 mg,The isolated yield was 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; | 2.2 step to take on the desired product I (1.0eq, 1.0mmol), copper acetate monohydrate (0.2eq, 0.2mmol), [PhIPh] PF6(2.0eq, 2.0mmol) in 1,2-dichloroethane, in an oil bath of 80 deg.] C reaction 48h, detected by TLC, After completion of the reaction, the reaction was quenched with water, extracted with ethyl acetate, dried over magnesium dried, and concentrated by rotary evaporation be isolated by column chromatography to give the desired product II (0.3170g, 94%) |
94% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
77% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; | 3.2 step to take on the desired product I (1.0eq, 1mmol), copper acetate monohydrate (0.2eq, 0.2mmol), [PhIPh] PF6(2.0eq, 2mmol) in 1,2-dichloroethane, in an oil bath of 80 deg.] C reaction 48h, detected by TLC, After completion of the reaction, the reaction was quenched with water, extracted with ethyl acetate, dried over magnesium sulfate , and concentrated by rotary evaporation be isolated by column chromatography to give the desired product II (0.2630g, 77%).MP = 119-121 .. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; | 1.2 step to take on the desired product I (1.0eq, 1mmol), copper acetate monohydrate (0.2eq, 0.2mmol), [PhIPh] PF6(2.0eq, 2mmol) in 1,2-dichloroethane, in an oil bath of 80 deg.] C reaction 48h, detected by TLC, After completion of the reaction, the reaction was quenched with water, extracted with ethyl acetate, dried over magnesium sulfate , and concentrated by rotary evaporation be isolated by column chromatography to give the desired product II (0.2360g, 73%). |
73% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. N-Phenyl-N-quinolin-8-ylbenzamide (3aa)Colorless solid; yield: 71 mg (73%); mp 125-128 °C. IR (KBr):3054, 1660, 1594, 1493, 1463, 1343, 1310, 1269, 1177, 1132,1075, 1028, 825, 789, 700 cm-1. 1H NMR (400 MHz, CDCl3):δ = 8.89-8.91 (m, 1 H), 8.07-8.09 (m, 1 H), 7.70-7.72 (m, 1 H),7.57-7.62 (m, 3 H), 7.45-7.49 (m, 1 H), 7.32-7.35 (m, 1 H),7.22-7.24 (m, 4 H), 7.09-7.16 (m, 4 H). 13C NMR (100 MHz,CDCl3): δ = 171.6, 150.7, 144.7, 144.4, 141.8, 136.8, 135.8, 129.7,129.3, 129.2, 128.9, 128.7, 127.6, 127.4, 126.9, 126.3, 125.8,121.6. HRMS (ESI): m/z [M + H]+ calcd for C22H17N2O:325.13354; found: 325.13327. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(I) triflate benzene complex In 1,2-dichloro-ethane at 120℃; for 8h; Inert atmosphere; regioselective reaction; | |
82% | With copper(I) triflate In 1,2-dichloro-ethane at 100℃; for 10h; | 3 Preparation of a compound of formula IVc At room temperature at 25 , 1.10mmol added diphenyliodonium hexafluorophosphate ion to a reaction tube 25mL, bis (methoxy-phenyl) ethynyl 0.15mmol trifluoromethanesulfonic acid and 1.20mmol of copper, was added 3mL dichloroethane was dissolved. Were then added 1.0mmol of N, N'- diisopropyl carbodiimide, the reaction 100 10 hours. The reaction system was dark red suspension. The reaction solution was filtered and concentrated, separated by silica gel column decolorization with petroleum ether: ethyl acetate = 4: 1 mixed solvent made eluent, to give quinoline-2-imine derivative (IVc) 365mg (purity> 98%, orange solid), 82% isolated yield |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(I) triflate benzene complex In 1,2-dichloro-ethane at 120℃; for 8h; Inert atmosphere; regioselective reaction; | |
60% | With copper(I) triflate In 1,2-dichloro-ethane at 100℃; for 10h; | 5 Preparation of a compound of formula IVb To a 25 mL reaction tube at room temperature of 25 ° C was added l.OO mmol of diphenyliodonium iodide hexafluorophosphate, 1. OOmmol of 1-p-nitrophenyl-2-p-methoxyphenylacetylene and 0.05 mmol of copper trifluoromethanesulfonate were added to a solution of 5 mL of dichloro Ethane dissolved. Then, l.Ommol of N, N '- diisopropylcarbodiimide was added and reacted at 100 ° C for 10 hours. The reaction system is deep Red suspension. The reaction solution was filtered and concentrated, and the silica gel column was decolorized. The mixture was treated with a mixed solvent of petroleum ether: ethyl acetate = 4: 1 Eluent to give 272 mg (purity & gt; 98%, red solid) of quinoline-2-imine derivative (IVe), and the isolated yield was 60% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With copper(I) triflate benzene complex In 1,2-dichloro-ethane at 120℃; for 8h; Inert atmosphere; regioselective reaction; | |
74% | With copper(I) triflate In 1,2-dichloro-ethane at 120℃; for 6h; | 7 Preparation of a compound of formula IVg To a 25 mL reaction tube at room temperature of 25 ° C was added l.OO mmol of diphenyliodonium iodide hexafluorophosphate, 1 · 20mmo 1 of phenyl-trimethylsilylacetylene and 0.05mmo 1 of copper trifluoromethanesulfonate were added and dissolved in 5 mL of dichloroethane. Then Followed by l.Ommol of N, N '- diisopropylcarbodiimide followed by reaction at 120 ° C for 6 hours. The reaction system is a deep red suspension. Too Filtering and concentrating the reaction solution, separating the Era Er column with a petroleum ether: ethyl acetate = 4: 1 as the eluent to obtain the quin 2-imine derivative (IVg) 278 mg (Purity & gt; 98%, yellow solid), 74% isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(I) triflate benzene complex In 1,2-dichloro-ethane at 120℃; for 8h; Inert atmosphere; regioselective reaction; | |
78% | With copper(I) triflate In 1,2-dichloro-ethane at 100℃; for 10h; | 6 Preparation of a compound of formula IVf At a temperature of 40 ° C, to a 25 mL reaction tube L.OO mmol diphenyl iodide ion ion hexafluorophosphate, 1.20 mmol of phenyl-cyclohexylacetylene and 0.05 mmol of cuprous trifluoromethanesulfonate, Add 5mL of dichloro ethylene to dissolve. Followed by the addition of l.Ommol of N, N '- diisopropylcarbodiimide, 100 ° C for 10 hours. The reaction system is a deep red suspension. The reaction solution was filtered and concentrated, and the silica gel column was decolorized, A mixture of petroleum ether: ethyl acetate = 4: 1 was used as the eluent, To obtain 301 mg of quinoline-2-imine derivative (IVf) (Purity> 98%, yellow solid), isolated yield 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(I) triflate benzene complex In 1,2-dichloro-ethane at 120℃; for 8h; Inert atmosphere; regioselective reaction; | |
75% | With copper(I) triflate In 1,2-dichloro-ethane at 100℃; for 10h; | 8 preparation of compounds of formula IVh At a temperature of 25 ° C, l.OO mmol was added to a 25 mL reaction tube Diphenyl iodide ion ion hexafluorophosphate, 1 · 20 mmol of diphenylacetylene and 0.05 mmol of cuprous trifluoromethanesulfonate, Add 5mL of dichloro ethylene to dissolve. Then join 1. Ommol of N, N '-dicyclohexylcarbodiimide, 100 ° C for 10 hours. The reaction system is a deep red suspension. Filter and Concentrated reaction solution, silica gel column decolorization separation, with petroleum ether: Ethyl acetate = 4: 1 as the eluent, 345 mg of the quinoline-2-imine derivative (IVh) was obtained (purity> 98% Yellow solid), the separation yield 75% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere; Schlenk technique; | General Procedure: The preparation of 4-aryl quinolin-2(1H)-ones. General procedure: Pd(PPh3)4 (0.025 mmol, 0.1eq), ortho-aminocinnamate ester (0.5 mmol, 1.0 equiv.) and diphenyliodonium salts (1.0 mmol, 2.0 equiv.) were added to a dried Schlenk tube. The tube was degassed with Nitrogen for three times. Then DMF (2.0 mL) were added via a syringe. The mixture was stirred at 120 oC for 12 h, and then cooled down to room temperature. The crude products were directly purified using flash column chromatography on silica gel (petroleum ether/ethyl acetate 2:1 as eluants) to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 2-ethylmalononitrile With potassium <i>tert</i>-butylate In dichloromethane at 0℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: diphenyliodonium hexafluorophosphate In dichloromethane at 0 - 20℃; for 1.08333h; Schlenk technique; Inert atmosphere; | General Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried Schlenk tube was charged with 2-substitutedmalononitriles (0.5 mmol, 1 equiv), the tube was evacuated andcharged with nitrogen, then 2 mL anhydrous DCM and t-BuOK(61.7 mg, 0.55 mmol, 1.1 equiv) were added, and the mixturewas stirred at 0 °C for 5 min. The solution of diaryliodoniumsalts (0.55 mmol, 1.1 equiv) in 2 mL anhydrous DCM was addedthrough a syringe subsequently for 5 min. The reaction wasstirred for another 1 h, and the reaction temperature was elevatedto r.t. The reaction mixture was quenched with 20 mLwater, then the mixture was extracted with EtOAc (3 × 10 mL).The combined extracts were washed with brine, dried overNa2SO4, and filtered. After the solvent was removed undervacuum, and the residue was purified by flash chromatographyto give the desired product. Analytical data for representativesample 3a is provided below.2-Ethyl-2-phenylmalononitrile (3a)81.7 mg (96% yield), colorless oil. 1H NMR (400 MHz, CDCl3): δ =7.58-7.53 (m, 2 H), 7.52-7.45 (m, 3 H), 2.29 (q, J = 7.4 Hz, 2 H),1.23 (t, J = 7.4 Hz, 3 H). 13C NMR (101 MHz, CDCl3): δ = 132.0,129.9, 129.7, 125.8, 115.0, 43.2, 36.6, 10.0. HRMS (EI): m/z calcdfor C11H10N2 [M]+: 170.0844; found: 170.0843. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With copper(II) bis(trifluoromethanesulfonate); sodium phosphate; (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole) In toluene at 80℃; for 15h; Inert atmosphere; | 1 4.3. Typical procedure of chiral copper-catalyzed asymmetric monoarylation of vicinal diols with diaryliodonium triflates Under argon atmosphere, a reaction tube was charged with CuCl2 (6.7mg, 0.05mmol), (R,R)-Ph-BOX L1 (16.7mg, 0.05mmol), and sodium phosphate tribasic (492mg, 3.0mmol). After toluene (1.5mL) was added, the mixture was stirred at 80°C for 15min and cooled to room temperature. Then, cis-1,2-cyclooctanediol (1a) (144mg, 1.0mmol) and diphenyliodonium triflate (2a) (645mg, 1.5mmol) were added and the reaction mixture was stirred at 80°C for 15h. The mixture was cooled to room temperature, and water and saturated NH4Cl were added. The resulting mixture was extracted with CH2Cl2. The combined organic layers were dried over MgSO4. Concentration and purification through silica gel column chromatography gave desired product 3aa. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.38 g | With potassium tert-butylate; In tetrahydrofuran; at 40℃; | A 100-mL round-bottom flask was charged with <strong>[56962-13-1]2,4-dichloro-3-hydroxybenzaldehyde</strong> (0.380 g, 1.99 mmol, 1.00 equiv), potassium tert-butoxide (0.246 g, 2.19 mmol, 1.10 equiv), diphenyliodonium hexafluorophosphate (1.02 g, 2.39 mmol, 1.20 equiv), and tetrahydrofuran (10 mL). The resulting solution was stirred overnight at 40 C. and quenched with water (40 mL). The mixture was extracted with dichloromethane (3*30 mL) and the organic layers were combined, washed with water (3*10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide 0.380 g of 2,4-dichloro-3-phenoxybenzaldehyde as a yellow solid. LCMS (ESI, m/z): 267 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique; | N-Aryl-N-quinolin-8-ylaroylamides 3aa-3ma; General Procedure General procedure: An oven-dried Schlenk tube (10 mL) equipped with a magneticstirrer bar was charged with the appropriate N-quinolin-8-ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophosphate2 (0.6 mmol), Cu(OAc)2.H2O (20 mol%, 0.06 mmol), and 4Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, andthe mixture was stirred for 48 h at 80 °C in air. H2O (6 mL) wasadded to quench the reaction, and the resulting mixture wasextracted with EtOAc (×2). The combined organic extracts werewashed with brine, dried (Na2SO4), and concentrated. The crudeproduct was purified by flash column chromatography [silicagel, PE-EtOAc (3:1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.5% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,2-dichloro-ethane at 80℃; for 1h; Sealed tube; Inert atmosphere; | 4 Example 4 2-Nitrocyclohexanone (28.6 mg, 0.20 mmol) was added sequentially to a dry 10 mL sealed tube.DBU (1,8-diazacyclo[5,4,0]undecene-7) (29.9 uL, 0.20 mmol) and diphenyliodonium hexafluorophosphate (Ph2IPF6, CAS: 58109-40-3) (225.6mg, 0.60mmol), then add 5.0mL DCE under argon atmosphere, sealed with lid, in 80 ° C oil bathReaction for 1 hour. After the raw materials are consumed, the system is cooled to room temperature, then diluted with 6.0 mL of petroleum ether, directlyColumn chromatography (petroleum ether / ethyl acetate = 40:1). Finally, a pale yellow solid (20.8 mg, yield 47.5%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With o-phenylenebis(diphenylphosphine); sodium acetate; palladium diacetate In dichloromethane at 20℃; for 16h; Inert atmosphere; | 4.21. General Procedure B: synthesis of aryl-butenolides using palladium General procedure: To a flame dried vial was added palladium acetate (5 mol%) and1,2-bis(diphenylphosphino)benzene (5 mol%), followed by the iodonium salt (1 eq) and sodium acetate (0.8 eq). The reaction vial was then pump and backfilled with nitrogen three times. Once under a nitrogen atmosphere, dichloromethane (0.052 M) was added, followed by the silyl enol ether (2 eq). The reaction was stirred for 16 h at room temperature under nitrogen atmosphere. After 16 h, the reaction mixture was extracted three times with diethyl ether. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2) using a 50:50 diethyl ether/hexanes to afford the desired product as a colorless or yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium hydrogencarbonate; triphenylphosphine; palladium dichloride; In dimethyl sulfoxide; at 140℃; for 24h;Sealed tube; | This method refers to the sequential bis(phenyl) hexafluorophosphate iodide salt,Oxazole,Palladium chloride,Triphenylphosphine and sodium bicarbonate,The dimethyl sulfoxide was uniformly mixed, and the reaction was sealed at 140 C for 24 hours.Wherein: the molar ratio of oxazole to bis(phenyl) hexafluorophosphate iodide is 1:1.3; the molar ratio of oxazole to palladium chloride is 10:4;The molar ratio of oxazole to sodium hydrogencarbonate is 1:4;The molar ratio of oxazole to triphenylphosphine is 3:1.The reaction process was followed by thin layer chromatography as described in Example 1 to obtain a reaction solution;The reaction solution was sequentially extracted, dried, and subjected to the method described in Example 1.After concentration and column chromatography separation, 2,5-diphenyloxazole is obtained.The yield was 76%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 24h; Sealed tube; | 10 Embodiment 10 A method for preparing a 2,5-diaryl five-membered heterocyclic aromatic hydrocarbon which comprises sequentially iodonium di(phenyl)hexafluorophosphate,4-methylthiophene, palladium acetate, triphenylphosphine and cesium carbonate,Dimethylformamide is mixed evenly,The reaction was sealed at 140 ° C for 24 hours.Wherein: the molar ratio of 4-methylthiophene to bis(phenyl)hexafluorophosphate iodide is 1:1.4;The molar ratio of 4-methylthiophene to palladium acetate was 10:3; the molar ratio of 4-methylthiophene to cesium carbonate was 1:2; and the molar ratio of 4-methylthiophene to triphenylphosphine was 2:1.The reaction process was followed by thin layer chromatography as described in Example 1 to obtain a reaction solution; the reaction solution was subjected to extraction, drying, concentration, column chromatography and separation according to the method described in Example 1.That is, 4-methyl-2,5-diphenylthiophene,The yield was 86%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper(II) acetate hydrate In N,N-dimethyl-formamide at 115℃; for 18h; | Synthesis of 9-((9- (4- (tert-butyl) pyridin-2-yl) -9H-carbazol-2-yl) Oxy) -6,6-dimethyl-2-phenyl-6H-imidazo [4,5,1-de] acridine2-ium hexafluorophosphate SC (SC2018-2-054): 9-((9- (4- (tert-butyl) pyridin-2-yl) -9H-carbazol-2-yl) oxy) -6,6-dimethyl-6H-imidazo [4,5,1- De] acridine (1.5 g, 2.73 mmol), A mixture of diphenyliodonium PF6 (1.398 g, 3.28 mmol) and diacetoxy copper hydrate (0.027 g, 0.137 mmol) was depressurized several times and refilled with nitrogen.DMF (11 ml) was added to the reaction mixture and heated at 115 ° C. for 18 hours. The DMF is then removed and the resulting solids are placed on celiteCoated and chromatographed on silica (ACN / DCM = 1/9) (91%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper; copper(l) chloride In 1,1,2,2-tetrachloroethane at 50℃; for 1h; Inert atmosphere; | General Procedure for the Preparation of Diaryl Phosphiranium Salts 6 General procedure: To a solution of phosphirane 1 (1 equiv) in 1,1,2,2-tetrachloroethane (0.1 M) were added diphenyliodonium salt (1.2 equiv), copper chloride (10 mol%), and copper metal wire (cat.) at room temperature. The reaction mixture was then heated at 50 °C. After cooling down to room temperature, the resulting crude mixture was directly purified by flash column chromatography on silica gel (eluent: CH2Cl2 then CH2Cl2/acetone, 60:40) to yield the title product 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.2% | With N-ethyl-N,N-diisopropylamine In acetonitrile Inert atmosphere; Heating; | 3 Example 3 Add Tenofovir 28.7g (0.10mol, 1.0equiv), diphenyliodonium hexafluorophosphate 36.8g (0.10mol, 1.0equiv), and 14.2 diisopropylethylamine to the reactor under nitrogen protection g(0.11mol, 1.1equiv), 200ml acetonitrile, heated to reflux, TLC detection to control the end of the reaction, when the reaction is over, reduce the temperature to 0, add 150ml of dichloromethane, add dilute hydrochloric acid to adjust the pH to below 1, and divide the organic The aqueous layer was slowly added with sodium carbonate solid to adjust the pH to 2 to 3, stirred for half an hour, filtered, and dried to obtain 30.6 g of white solid tenofovir monophenyl ester with a molar yield of 84.2% and an HPLC purity of 97.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(II) bis(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 24 h / 70 °C 2: C26H46Cl2Ni; potassium phosphate / toluene / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper (II) acetate In N,N-dimethyl-formamide at 120℃; for 20h; Schlenk technique; | Starting ether (0.42 grams, 0.71 mmol), diphenyliodonium salt (0.363 grams, 0.853 mmol) and copper (II) acetate (7.10 mg, 0.036 mmol) were added to a 25 mL Schlenk tube. Dimethylformamide (3 mL) was added and the reaction was stirred at 120° C. for 20 hours. The crude mix was diluted with dichloromethane and successively washed with water. Column chromatography (silica gel) eluting with 20% ethyl acetate in DCM gave 0.38 grams (66% yield) of desire product as a white solid. |
Tags: 58109-40-3 synthesis path| 58109-40-3 SDS| 58109-40-3 COA| 58109-40-3 purity| 58109-40-3 application| 58109-40-3 NMR| 58109-40-3 COA| 58109-40-3 structure
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