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HazMat fee for 500 gram (Estimated)
Excepted Quantity
USD 0.00
Limited Quantity
USD 15-60
Inaccessible (Haz class 6.1), Domestic
USD 80+
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Structure of 66003-76-7 * 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] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 639 - 647
8
[ 66003-76-7 ]
[ 591-50-4 ]
[ 1591-31-7 ]
[ 2113-51-1 ]
[ 20442-79-9 ]
[ 71-43-2 ]
Reference：
[1] Journal of Organic Chemistry, 1991, vol. 56, # 5, p. 1838 - 1844
9
[ 66003-76-7 ]
[ 591-50-4 ]
[ 92-52-4 ]
[ 2051-60-7 ]
[ 1591-31-7 ]
[ 2113-51-1 ]
[ 20442-79-9 ]
Reference：
[1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 639 - 647
10
[ 66003-76-7 ]
[ 591-50-4 ]
[ 92-52-4 ]
[ 1591-31-7 ]
[ 2113-51-1 ]
[ 20442-79-9 ]
[ 100-66-3 ]
Reference：
[1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 639 - 647
11
[ 66003-76-7 ]
[ 591-50-4 ]
[ 92-52-4 ]
[ 1591-31-7 ]
[ 2113-51-1 ]
[ 20442-79-9 ]
[ 103-84-4 ]
Reference：
[1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 639 - 647
12
[ 66003-76-7 ]
[ 75-05-8 ]
[ 591-50-4 ]
[ 1591-31-7 ]
[ 2113-51-1 ]
[ 20442-79-9 ]
[ 103-84-4 ]
[ 71-43-2 ]
Reference：
[1] Journal of Organic Chemistry, 1991, vol. 56, # 5, p. 1838 - 1844
13
[ 533-58-4 ]
[ 66003-76-7 ]
[ 34883-46-0 ]
Reference：
[1] Organic Letters, 2011, vol. 13, # 6, p. 1552 - 1555
[2] Chemistry--A European Journal, 2012, vol. 18, # 44, p. 14140 - 14149,10
14
[ 66003-76-7 ]
[ 95-53-4 ]
[ 1205-39-6 ]
[ 4316-55-6 ]
Reference：
[1] Journal of Organic Chemistry, 2017, vol. 82, # 22, p. 11933 - 11938
15
[ 103-90-2 ]
[ 66003-76-7 ]
[ 6312-87-4 ]
Reference：
[1] Organic Letters, 2011, vol. 13, # 6, p. 1552 - 1555
[2] Chemistry--A European Journal, 2012, vol. 18, # 44, p. 14140 - 14149,10
[3] Organic Letters, 2015, vol. 17, # 11, p. 2688 - 2691
16
[ 591-50-4 ]
[ 1493-13-6 ]
[ 71-43-2 ]
[ 66003-76-7 ]
Yield
Reaction Conditions
Operation in experiment
88%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1 h; Reflux
An oxidant of 5.5 mmol of m-chloroperoxybenzoic acid is added to the reactor in the order of5.5mmol iodobenzene, 15mL dichloromethane solution, 5mmol benzene,10 mmol trifluoromethanesulfonic acidAnd one of the 5 magnets,Condensate is condensate from bottom to top at room temperature.Add to the reactor for condensation reflux,Place the reactor in a 40°C oil bath and heat it.The reaction was stirred for 1 hour with magnetic stirring; the reaction solution was spin-dried in a rotary evaporator (40°C water bath).After adding 20 ml of diethyl ether and stirring at room temperature for half an hour,Place in a medical refrigerator at 0-4°C for 15 minutes, remove and use ether as eluent.Filtered on a Buchner funnel,After the product is filtered by suction, it is left on the filter paper and the product is dried in a drying oven at 100°C for 24 hours.That is, the diaryl iodonium triflate was obtained in a yield of 88percent.The pressure was reduced under spin-dry conditions 0.1 MPa, 40°C.
Reference：
[1] Organic Letters, 2011, vol. 13, # 13, p. 3462 - 3465
[2] Chemistry--A European Journal, 2012, vol. 18, # 44, p. 14140 - 14149,10
[3] Organic Letters, 2015, vol. 17, # 18, p. 4554 - 4557
[4] Organic Letters, 2015, vol. 17, # 11, p. 2688 - 2691
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 31, p. 8928 - 8932[6] Angew. Chem., 2016, vol. 128, # 31, p. 9074 - 9078,5
[7] Organic Letters, 2018, vol. 20, # 7, p. 1978 - 1981
[8] Chemical Communications, 2018, vol. 54, # 64, p. 8810 - 8813
[9] Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11226 - 11230[10] Angew. Chem., 2016, vol. 128, # 37, p. 11392 - 11396,5
[11] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11427 - 11431[12] Angew. Chem., 2018, vol. 130, # 35, p. 11597 - 11601,5
[13] Advanced Synthesis and Catalysis, 2007, vol. 349, # 17-18, p. 2610 - 2618
[14] Organic Syntheses, 2009, vol. 86, p. 308 - 314
[15] Organic Letters, 2011, vol. 13, # 6, p. 1552 - 1555
[16] Chemistry - A European Journal, 2014, vol. 20, # 29, p. 8888 - 8892
[17] Chemical Communications, 2007, # 24, p. 2521 - 2523
[18] European Journal of Organic Chemistry, 2016, vol. 2016, # 12, p. 2096 - 2100
[19] Angewandte Chemie - International Edition, 2017, vol. 56, # 25, p. 7161 - 7165[20] Angew. Chem., 2017, vol. 129, # 25, p. 7267 - 7271,5
[21] Journal of Organic Chemistry, 2017, vol. 82, # 22, p. 11735 - 11741
[22] Patent: CN107759465, 2018, A, . Location in patent: Paragraph 0019; 0020; 0021; 0022
[23] European Journal of Organic Chemistry, 2012, # 25, p. 4675 - 4679
[24] Angewandte Chemie - International Edition, 2016, vol. 55, # 31, p. 9084 - 9087[25] Angew. Chem., 2016, vol. 128, # 31, p. 9230 - 9233,4
[26] ChemistryOpen, 2017, vol. 6, # 1, p. 18 - 20
[27] Advanced Synthesis and Catalysis, 2012, vol. 354, # 18, p. 3517 - 3522
[28] Letters in Organic Chemistry, 2013, vol. 10, # 8, p. 541 - 548
[29] Journal of Organic Chemistry, 2014, vol. 79, # 18, p. 8607 - 8613
[30] Organic Letters, 2016, vol. 18, # 4, p. 736 - 739
[31] Angewandte Chemie - International Edition, 2017, vol. 56, # 14, p. 3961 - 3965[32] Angew. Chem., 2017, vol. 129, # 14, p. 4019 - 4023,5
17
[ 1493-13-6 ]
[ 1483-73-4 ]
[ 66003-76-7 ]
Reference：
[1] Journal of the American Chemical Society, 2008, vol. 130, # 26, p. 8172 - 8174
[2] Bulletin of the Chemical Society of Japan, 1997, vol. 70, # 1, p. 219 - 224
18
[ 1493-13-6 ]
[ 71-43-2 ]
[ 66003-76-7 ]
Reference：
[1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 17-18, p. 2610 - 2618
[2] Organic Letters, 2011, vol. 13, # 6, p. 1552 - 1555
[3] Chemistry--A European Journal, 2012, vol. 18, # 44, p. 14140 - 14149,10
[4] Organic Syntheses, 2009, vol. 86, p. 308 - 314
[5] Organic Letters, 2018, vol. 20, # 7, p. 1936 - 1940
[6] Chemical Communications, 2007, # 24, p. 2521 - 2523
[7] Chemistry - A European Journal, 2015, vol. 21, # 47, p. 16801 - 16806
[8] Synlett, 2014, vol. 25, # 14, p. 2009 - 2012
[9] Chinese Journal of Chemistry, 2018, vol. 36, # 1, p. 11 - 14
In 2,2,2-trifluoroethanol; at 70℃; for 14h;Sealed tube;
General procedure: Diphenyliodonium triflate (2a, 0.1 g, 0.23 mmol, 1.1 equiv) was charged in a vial and sealed with a septum. After adding TFE (3mL), indoline (1a, 0.024 mL, 0.21 mmol) was added dropwise slowly to the solution, which was then heated to 70 C for 14 h.After the solution was cooled to r.t., the mixture was diluted with H2O and sat. NaHCO3. The aqueous phase was extracted several times with CH2Cl2. The organic phase is washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel, eluting with cyclohexane-CH2Cl2 (2:1, v/v) giving 34 mg(83%) of 3a as a colorless solid.
tert-butyl methylsulfonyl(phenyl)carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
With triethylamine; copper(l) chloride; In toluene; at 20℃; for 8h;
General procedure: A 10 mL round bottom flask was charged with a diaryliodonium salt (0.325 mmol), CuCl (10 mol %), triethylamine (0.50 mmol), and the corresponding tert-butyl N-sulfonylcarbamate (0.25 mmol). Toluene (2 mL) was then added to the flask. The reaction mixture was stirred at room temperature. After completion of the reaction, as monitored by TLC analysis, the solvent was removed in vacuo and the residue was purified by flash column chromatography on silica gel to obtain the desired product.
tert-butyl (4-nitrophenyl)sulfonyl(phenyl)carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%
With triethylamine; copper(l) chloride; In toluene; at 20℃; for 24h;
General procedure: A 10 mL round bottom flask was charged with a diaryliodonium salt (0.325 mmol), CuCl (10 mol %), triethylamine (0.50 mmol), and the corresponding tert-butyl N-sulfonylcarbamate (0.25 mmol). Toluene (2 mL) was then added to the flask. The reaction mixture was stirred at room temperature. After completion of the reaction, as monitored by TLC analysis, the solvent was removed in vacuo and the residue was purified by flash column chromatography on silica gel to obtain the desired product.
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation;
General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields.
(4-benzoylphenyl)(phenyl)(p-tolyl)sulfonium triflate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%
With copper(l) iodide; copper; In 1,1,2,2-tetrachloroethane; at 110℃; for 2.0h;
Phenyl(4-(p-tolylthio)phenyl)methanone (1 mol), diphenyliodonium triflate (1.2 mol) and 1,1,2,2-tetrachloroethane (2 mL) were placed in a 50-mL roundbottom flask equipped with a mechanical stirrer, thermometer and reflux condenser. After thoroughly mixing, the combination of CuI (5 mmol %) and Cu (5 mmol %)was added as catalyst. The reaction mixture was stirred for 2 h at 110 C. The resulting mixture was cooled, filtered and then excess solvent was evaporated under reduced pressure. The crude product was purified by silica gel chromatography (dichloromethane: ethyl acetate = 7:3) to afford S-arylsulfonium salts 2. (4-Benzoylphenyl)(phenyl)(p-tolyl)sulfonium triflate 2a Light yellow viscous liquid. 1H NMR (CDCl3) d: 2.53-2.58 (s, CH3, 3H), 7.53-7.62 (m, ArH, 4H),7.67-7.73 (m, ArH, 3H), 7.79-7.87 (m, ArH, 9H), 8.04-8.07 (m, ArH, 2H). 13CNMR (DMSO) d: 20.92, 119.98, 124.17, 128.21, 128.46, 129.44, 130.53, 130.72, 131.04, 131.27, 131.76, 133.05, 134.18, 135.28, 141.63, 145.77, 193.57. HRMS(ESI) clacd for C26H21OS (M+ OTf)+: 381.1347, found: 381.1303.
With copper(II) bis(trifluoromethanesulfonate); In N,N-dimethyl-formamide; at 150℃; for 10h;Inert atmosphere; Schlenk technique;
General procedure: Under the condition of nitrogen (N2) protection,Add in 25mL Schlenk bottlesa compound of formula IIa (1.65 mmol, 3.3 equiv),Cu(OTf) 2 (0.15 mmol, 0.3 equiv, catalyst),Add the formula Iq with a syringeCompound (0.5 mmol, 1.0 equiv) and 5 mL of DMF,Reacting at 150 C for 10 hours,Add 20mL of water,Extract three times with 10 mL of ethyl acetate.Na2SO4 is dry,Spin the solvent,Separation and purification on silica gel column (leaching agent:Petroleum ether / ethyl acetate = 50/1, by volume),The target product (compound represented by formula a) was obtained in a yield of 87%.
With water; potassium carbonate; In dichloromethane; at 100℃; for 12h;Sealed tube; Inert atmosphere;
Weighed diphenyl iodonium triflate (0.5 mmol, 215 mg), potassium carbonate (0.5 mmol, 69 mg)In a 25 mL sealed tube, a magnetic charge was added, and after replacing the air in the sealed tube three times with high-purity nitrogen, <strong>[143825-84-7]1-phenyl-1-vinylboronic acid pinacol ester</strong> (1 mmol, 230 mg) was added to the sealed tube under nitrogen protection. 2.5 mL of dichloromethane, deionized water (20 mmol, 333 mul)The tube was tightly sealed, transferred to an oil bath at 100 C and stirred for 12 h. TLC detection and tracking reaction, after the reaction is over, willThe tube was cooled to room temperature. Add 5 mL of distilled water to the system to quench the reaction, stir; extract 3 times with 5 mL of dichloromethane, and combineThe machine phase was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator to obtain a crude product; the crude product was loaded on silica gel, eluentAfter purification by column chromatography using a volume ratio of petroleum ether: ethyl acetate = 50:1The pure 1-phenyl-2-phenylethylene boronic acid pinacol ester was obtained as a white solid, and the isolated yield was 57%.
With copper; caesium carbonate; In acetonitrile; at 80℃; for 24h;
General procedure: A catalyst (8 mol%), 1-acyl-1H-1,2,3-benzotriazoles (0.2 mmol),Cs2CO3 (0.4 mmol), diaryliodonium salts (0.4 mmol) and acetonitrile(3.0 mL) were sequentially added into a 25mL round-bottom flask, and the mixture was stirred in a preheated oil bath at 80 Cfor 24 h. Then the resulting mixture was cooled to r.t. and the solventwas removed in vacuum. The crude product was purified bycolumn chromatography on silica gel with ethyl acetate/petroleumether (1:10 vol) as an eluent to give the desired 1-aryl-1H-1,2,3-benzotriazoles.
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