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[ CAS No. 4381-25-3 ] {[proInfo.proName]}

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Chemical Structure| 4381-25-3
Chemical Structure| 4381-25-3
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Product Details of [ 4381-25-3 ]

CAS No. :4381-25-3 MDL No. :MFCD00051933
Formula : C7H9NOS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 155.22 Pubchem ID :-
Synonyms :

Safety of [ 4381-25-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330-P501 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4381-25-3 ]

* 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.

  • Downstream synthetic route of [ 4381-25-3 ]

[ 4381-25-3 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 3857-83-8 ]
  • [ 4381-25-3 ]
  • N-(2-naphthyl)-S-phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃;
  • 2
  • [ 99747-74-7 ]
  • [ 4381-25-3 ]
  • rac-N-[1-naphthyl]-S-phenyl-S-methylsulfoximine [ No CAS ]
  • 3
  • [ 3017-70-7 ]
  • [ 4381-25-3 ]
  • S-methyl-N-(3-methylbut-2-en-2-yl)-S-phenylsulfoximine [ No CAS ]
  • 4
  • [ 557-93-7 ]
  • [ 4381-25-3 ]
  • S-methyl-S-phenyl-N-(propen-2-yl)sulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate; N,N`-dimethylethylenediamine In toluene at 110℃; for 24h;
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 24h; Heating;
  • 5
  • [ 3017-69-4 ]
  • [ 4381-25-3 ]
  • S-methyl-N-(2-methylprop-1-en-1-yl)-S-phenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; N,N`-dimethylethylenediamine In toluene at 110℃; for 24h;
  • 6
  • [ 52414-97-8 ]
  • [ 4381-25-3 ]
  • [ 852317-11-4 ]
  • 7
  • [ 446-09-3 ]
  • [ 4381-25-3 ]
  • [ 852317-12-5 ]
  • 8
  • [ 5326-39-6 ]
  • [ 4381-25-3 ]
  • [ 852317-13-6 ]
  • 9
  • [ 62674-71-9 ]
  • [ 4381-25-3 ]
  • N-(6-methyl-2-pyridinyl)-S-methyl-S-phenylsulfoximine [ No CAS ]
  • 10
  • [ 6324-50-1 ]
  • [ 4381-25-3 ]
  • rac-N-[2,4,6-(trichloro)phenyl]-S-methyl-S-phenylsulfoximine [ No CAS ]
  • 11
  • [ 4381-25-3 ]
  • [ 103008-51-1 ]
  • [ 864443-52-7 ]
  • 12
  • [ 1679-18-1 ]
  • [ 4381-25-3 ]
  • [ 56158-15-7 ]
YieldReaction ConditionsOperation in experiment
93% In methanol at 20℃; for 12h;
88% With dmap; copper(l) iodide In methanol at 20℃; for 0.75h; N-Arylation of Sulfoximines with Arylboronic Acids; General Procedure General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 mol%), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products.
47% With copper diacetate In methanol at 20℃; for 24h; Schlenk technique;
  • 13
  • [ 13922-41-3 ]
  • [ 4381-25-3 ]
  • rac-N-[1-naphthyl]-S-phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With dmap; copper(l) iodide In methanol at 20℃; for 0.75h; N-Arylation of Sulfoximines with Arylboronic Acids; General Procedure General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 mol%), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products.
62% In methanol at 20℃; for 12h;
  • 14
  • [ 4381-25-3 ]
  • [ 159191-56-7 ]
  • rac-N-[(4-t-butyl-dimethylsilyloxy)phenyl]-S-phenyl-S-methylsulfoximine [ No CAS ]
  • 15
  • [ 349-03-1 ]
  • [ 4381-25-3 ]
  • rac-N-[2-(nitro)-4-(trifluoromethyl)phenyl]-S-methyl-S-phenylsulfoximine [ No CAS ]
  • 16
  • [ 349-03-1 ]
  • [ 4381-25-3 ]
  • [ 872087-55-3 ]
  • 17
  • [ 4381-25-3 ]
  • [ 52833-94-0 ]
  • [ 1027729-84-5 ]
YieldReaction ConditionsOperation in experiment
84% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 60℃; for 20h; Example 469 <n="79"/>(S)-2-amino-5-[(3-hydroxyphenyl)ethynyl]-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamideStep 1(S)-2-amino-5-bromo-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide To a solution of <strong>[52833-94-0]2-amino-5-bromonicotinic acid</strong> (189 mg, 0.87 mmol), N, N- diisopropylethylamine (0.30 mL, 1.7 mmol), and (S)-(+)-S-methyl-S-phenylsulfoximine (162 mg, 1.0 mmol) in 4.0 mL DMF at room temperature was added BOP (423 mg, 0.96 mmol). The solution was stirred 30 minutes, then heated at 60 0C for 30 minutes, and then cooled back to room temperature. After 19 hours, the mixture was dissolved in EtOAc, washed with Na2CO3 solution, H2O, brine, dried with anhydrous Na2Spsi4 and rotary evaporated. The yellow foam was purified by chromatography (silica gel, CHCl3/EtOAc) to give the title compound as a light yellow solid (260 mg, 84percent).
  • 18
  • [ 829-35-6 ]
  • [ 4381-25-3 ]
  • [ 1261274-33-2 ]
  • 19
  • [ 2875-18-5 ]
  • [ 4381-25-3 ]
  • [ 1261274-45-6 ]
  • 20
  • [ 622-98-0 ]
  • [ 4381-25-3 ]
  • [ 1316303-49-7 ]
  • 21
  • [ 939-80-0 ]
  • [ 4381-25-3 ]
  • [ 1316303-51-1 ]
  • 22
  • [ 84563-54-2 ]
  • [ 4381-25-3 ]
  • N-[(4-(tert-butyl)phenyl)]-S-methyl-S-phenylsulfoximine [ No CAS ]
  • 23
  • [ 3113-71-1 ]
  • [ 4381-25-3 ]
  • [ 1426922-73-7 ]
YieldReaction ConditionsOperation in experiment
64% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; Schlenk technique;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 13h; Schlenk technique; Inert atmosphere;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0 - 20℃; for 12h; Schlenk technique;

  • 24
  • [ 1074-12-0 ]
  • [ 4381-25-3 ]
  • N-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]-2-oxo-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tert.-butylhydroperoxide; copper(I) bromide In water; acetonitrile at 80℃; for 12h;
51% With oxygen; copper(I) bromide In acetonitrile at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
  • 25
  • [ 769-26-6 ]
  • [ 4381-25-3 ]
  • N-(2,4,6-trimethyl-phenylethynyl)-S,S-methylphenylsulfoximine [ No CAS ]
  • 26
  • [ 3240-10-6 ]
  • [ 4381-25-3 ]
  • [ 1498210-65-3 ]
YieldReaction ConditionsOperation in experiment
82% With pyridine; potassium phosphate; oxygen; copper(I) bromide In toluene at 80℃; for 16h;
  • 27
  • [ 32340-38-8 ]
  • [ 4381-25-3 ]
  • [ 1498210-68-6 ]
  • 28
  • [ 834-14-0 ]
  • [ 4381-25-3 ]
  • N-[(4-methoxyphenyl)(phenyl)methyl]-S,S-methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With ferric(III) bromide; di-tert-butyl peroxide In neat (no solvent) at 90℃; for 48h; Schlenk technique; Molecular sieve;
  • 29
  • [ 831-81-2 ]
  • [ 4381-25-3 ]
  • N-[(4-chlorophenyl)(phenyl)methyl]-S,S-methylphenylsulfoximine [ No CAS ]
  • 30
  • [ 457-68-1 ]
  • [ 4381-25-3 ]
  • [ 1584154-78-8 ]
YieldReaction ConditionsOperation in experiment
88% With ferric(III) bromide; di-tert-butyl peroxide In neat (no solvent) at 90℃; for 48h; Schlenk technique; Molecular sieve;
79% With tetrabutylammonium perchlorate In acetonitrile; <i>tert</i>-butyl alcohol at 30℃; Electrolysis;
  • 31
  • [ 5969-83-5 ]
  • [ 4381-25-3 ]
  • [ 1608153-19-0 ]
  • 32
  • [ 3475-21-6 ]
  • [ 4381-25-3 ]
  • [ 1608153-23-6 ]
  • 33
  • [ 27012-22-2 ]
  • [ 4381-25-3 ]
  • [ 1608153-24-7 ]
  • 34
  • [ 50340-79-9 ]
  • [ 4381-25-3 ]
  • [ 1616087-96-7 ]
  • 36
  • [ 57951-72-1 ]
  • [ 4381-25-3 ]
  • C12H13NOS [ No CAS ]
  • C12H15NO2S [ No CAS ]
  • 37
  • [ 17873-01-7 ]
  • [ 4381-25-3 ]
  • rac-N-[(4-methyl)-phenyl]-S-phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;
  • 38
  • [ 35692-27-4 ]
  • [ 4381-25-3 ]
  • [ 83706-37-0 ]
YieldReaction ConditionsOperation in experiment
77% With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;
  • 39
  • [ 35692-30-9 ]
  • [ 4381-25-3 ]
  • [ 56158-15-7 ]
  • 40
  • [ 4381-25-3 ]
  • [ 31680-08-7 ]
  • C15H14N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In hexane; water; for 12h;Inert atmosphere; Reflux; General procedure: To a flame-dried 10 mL Schlenk tube under N2 was added NH-sulfoximine 1 (0.3 mmol), aldehyde 3 (4.0 equiv), and TBAI (20 mol%), followed by n-hexane (1 mL). TBHP (2.0 equiv, 70% aqueous solution) was added after the starting materials were dissolved. The reaction mixture was then heated to reflux. After completion, the reaction was cooled to room temperature and quenched with saturated Na2S2O3, extracted by EA. The organic layer was washed by saturated brine, dried over anhydrous sodium sulfate. After the mixture was filtered and evaporated, the residue was purified by flash column chromatography to afford the desired N-acylsulfoximine 3.
  • 41
  • [ 21643-42-5 ]
  • [ 4381-25-3 ]
  • (Z)-N-[2-bromo-2-(n-tetradecyloxycarbonyl)]vinyl-S-phenyl-S-methyl sulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride; lithium bromide In toluene at 80℃; for 48h; Schlenk technique; stereoselective reaction;
  • 42
  • [ 21643-42-5 ]
  • [ 4381-25-3 ]
  • (Z)-N-[2-(n-tetradecyloxycarbonyl)]vinyl-S-phenyl-S-methyl sulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride In toluene at 80℃; for 48h; Schlenk technique; stereoselective reaction;
  • 43
  • [ 71195-85-2 ]
  • [ 4381-25-3 ]
  • (Z)-N-{2-bromo-2-[(pentafluorophenoxy)carbonyl]vinyl-S-phenyl-S-methyl sulfoximine [ No CAS ]
  • 44
  • [ 4381-25-3 ]
  • [ 122-00-9 ]
  • N-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]-2-oxo-2-(p-tolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; di-tert-butyl peroxide In neat (no solvent) at 90℃; for 12h; Schlenk technique;
80% With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
48% With tert.-butylhydroperoxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine; sodium carbonate In water at 80℃; for 6h;
  • 45
  • [ 403-42-9 ]
  • [ 4381-25-3 ]
  • 2-(4-fluorophenyl)-N-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) iodide; di-tert-butyl peroxide In neat (no solvent) at 90℃; for 12h; Schlenk technique;
60% With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
45% With tert.-butylhydroperoxide; iodine; sodium carbonate In water at 80℃; for 6h;
  • 46
  • [ 4381-25-3 ]
  • [ 93-08-3 ]
  • N-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]-2-(naphthalen-2-yl)-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With copper(l) iodide; di-tert-butyl peroxide In neat (no solvent) at 90℃; for 12h; Schlenk technique;
82% With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
  • 47
  • [ 1192-62-7 ]
  • [ 4381-25-3 ]
  • N-(2-oxo-2-furanylacetyl)-S,S-methylphenyl sulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; di-tert-butyl peroxide In neat (no solvent) at 90℃; for 12h; Schlenk technique;
61% With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
  • 48
  • [ 88-15-3 ]
  • [ 4381-25-3 ]
  • N-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]-2-oxo-2-(thiophen-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) iodide; di-tert-butyl peroxide In neat (no solvent) at 90℃; for 12h; Schlenk technique;
60% With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
  • 49
  • [ 6140-17-6 ]
  • [ 4381-25-3 ]
  • [ 882282-90-8 ]
  • 50
  • [ 104-93-8 ]
  • [ 4381-25-3 ]
  • [ 1377585-48-2 ]
YieldReaction ConditionsOperation in experiment
91% With tert.-butylhydroperoxide; copper(l) iodide; water In neat (no solvent) at 80℃; for 20h; Schlenk technique; General procedure for the synthesis of 3 General procedure: A Schlenk tube (25 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 2 (0.5 mmol), CuI (9.5 mg, 5 mol%) in dry methyl arene 1 (3.5 mL), then TBHP (258 mg, 2.0 mmol, 70% in water) was added dropwise, and the reaction mixture was allowed to stir at 80 °C for 20 h. After cooling to room temperature, the mixture was filtered through a short celite pad and washed with chloroform (15 mL × 3). The filtrate was concentrated, and the oily crude product was purified by column chromatography using silica gel (200 - 300 mesh) as stationary phase and a mixture of n-hexane and ethyl acetate as eluent to give the N-aroylated sulfoximines 3.
82% With tert.-butylhydroperoxide; iodine; sodium carbonate In water at 80℃; for 6h;
  • 51
  • [ 6563-13-9 ]
  • [ 4381-25-3 ]
  • 6-methoxy-2-[(methyl(oxo)(phenyl)-λ6-sulfanylidene)amino]quinoline 1-oxide [ No CAS ]
  • 52
  • [ 4381-25-3 ]
  • [ 586-37-8 ]
  • 2-(3-methoxyphenyl)-N-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
  • 53
  • [ 1778-09-2 ]
  • [ 4381-25-3 ]
  • N-[2-oxo-2-(4-methylthiophenyl)acetyl]-S,S-methylphenyl sulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
  • 54
  • [ 2142-69-0 ]
  • [ 4381-25-3 ]
  • 2-(2-bromophenyl)-N-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Typical Experimental Procedure General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20mol%), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane-EtOAc(10:1-2:1) as eluent to give product 3aa.
  • 55
  • [ 201230-82-2 ]
  • [ 33775-94-9 ]
  • [ 4381-25-3 ]
  • N-((2-methylthio)benzoyl)-S-methyl-S-phenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;
80% With palladium 10% on activated carbon; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 8h; Green chemistry;
  • 56
  • [ 32865-61-5 ]
  • [ 201230-82-2 ]
  • [ 4381-25-3 ]
  • N-(2-hydroxybenzoyl)-S-methyl-S-phenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;
  • 57
  • [ 2402-97-3 ]
  • [ 4381-25-3 ]
  • N-[2-(3-bromo)pyridinyl]-S,S-methylphenylsulfoximine [ No CAS ]
  • N-[2-(5-bromo)pyridinyl]-S,S-methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 28% 2: 14% Stage #1: S-methyl-S-phenylsulfoximine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-bromopyridine N-oxide With bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In tetrahydrofuran at 25℃; for 15h; Inert atmosphere;
  • 58
  • [ 23569-17-7 ]
  • [ 4381-25-3 ]
  • N-[2-(4-tert-butyl)pyridinyl]-S,S-methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: S-methyl-S-phenylsulfoximine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-tert-butylpyridine N-oxide With bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In tetrahydrofuran at 25℃; for 15h; Inert atmosphere;
  • 59
  • [ 1074-98-2 ]
  • [ 4381-25-3 ]
  • methyl ((3-methyl-4-nitropyridin-2-yl)imino)(phenyl)sulfanone [ No CAS ]
  • 60
  • [ 4381-25-3 ]
  • [ 486-74-8 ]
  • N-[quinoline-4-carboxyl]-S-methyl-S-phenylsulfoximine [ No CAS ]
  • 61
  • [ 5744-56-9 ]
  • [ 4381-25-3 ]
  • N-[1,3-dimethyl-1H-pyrazole-5-carboxyl]-S-methyl-S-phenylsulfoximine [ No CAS ]
  • 62
  • [ 16494-36-3 ]
  • [ 67-66-3 ]
  • [ 4381-25-3 ]
  • [ 1616087-94-5 ]
YieldReaction ConditionsOperation in experiment
76% With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium hydroxide; In toluene; at 80℃; for 12h; General procedure: In a 25 mL tube were added sulfoximine (0.5 mmol), ArI (0.6 mmol), chloroform (5 mmol), KOH (3 mmol), Pd(OAc)2 (2 mol%), DBU (20 mol %) and toluene (2 mL). The vessel was then sealed with a Teflon cap and heated up to 80 C and stirred at the same temperature for 12 h. After completion (TLC), the vessel was cooled down to room temperature, and water (5 mL) was added. The resulting suspension was extracted with ethyl acetate (10 mL × 3). The organic layer was combined and dried with anhydrous Na2SO4. After filtration, the solvent in the acquired solution was removed under reduced pressure. The residue obtained therein was subjected to silica gel column chromatography to give the pure product by using mixed ethyl acetate and petroleum ether as the eluent (v/v = 3 : 1).
  • 63
  • [ 22649-28-1 ]
  • [ 4381-25-3 ]
  • N-[2H-chromene-3-carbonyl]-S-methyl-S-phenylsulfoximine [ No CAS ]
  • 64
  • [ 5381-25-9 ]
  • [ 4381-25-3 ]
  • C16H13NO2S2 [ No CAS ]
  • 65
  • [ 1079-02-3 ]
  • [ 4381-25-3 ]
  • C14H8(2)H5NO2S [ No CAS ]
  • 66
  • [ 57102-98-4 ]
  • [ 4381-25-3 ]
  • N-[9-ethyl-9H-carbazole-3-carboxylic]-S-methyl-S-phenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 13h; Schlenk technique; Inert atmosphere;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0 - 20℃; for 12h; Schlenk technique;
  • 67
  • [ 2215-89-6 ]
  • [ 4381-25-3 ]
  • N-4-(4,4'-oxydibenzoyl)-S-methyl-S-phenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 13h; Schlenk technique; Inert atmosphere;
  • 68
  • [ 4381-25-3 ]
  • [ 162401-32-3 ]
  • C24H21Cl2F2N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With TEMPO; 3,6?di?tert?butyl?9?mesityl?10?phenylacridin?10?ium tetrafluoroborate; oxygen; In 1,2-dichloro-ethane; at 37℃; for 14h;Sealed tube; Irradiation; General procedure: To a microwave vial equipped with a stir bar was added the substrate(1.0 equiv, 0.4-1.0 mmol), sulfoximine (2.0 equiv), photocatalyst(0.05 equiv), and TEMPO (0.2 equiv), then the vial wasclosed with a septum cap. DCE or MeCN (0.1 M) was added, andthe mixture was sparged with oxygen. The reaction mixturewas subsequently irradiated in a Hepatochem PhotoRedOx Duophotoreactor and two Kessil LED lamps (each 40 W, A160WE) ora PennOC photoreactor m1 (450 nm). For the reaction workup,the mixture was either directly evaporated or half-saturatedaqueous NaHCO3 solution was added followed by extraction (5 ×EtOAc, Na2SO4). Purification was performed using an automatedIsolera Spektra System or preparative HPLC as described inthe Supporting Information.
  • 69
  • [ 1092513-18-2 ]
  • [ 4381-25-3 ]
  • N-quinolin-6-yl-S-methyl-S-phenylsulfoximine [ No CAS ]
  • 70
  • [ 4381-25-3 ]
  • [ 175205-81-9 ]
  • (S)-methyl(phenyl)((4-(trifluoromethyl)pyridin-2-yl)imino)-λ6-sulfanone [ No CAS ]
  • 71
  • [ 4381-25-3 ]
  • [ 175205-81-9 ]
  • methyl(phenyl)((4-(trifluoromethyl)pyridin-2-yl)imino)-λ6-sulfanone [ No CAS ]
  • 72
  • [ 5980-97-2 ]
  • [ 4381-25-3 ]
  • [ 1200799-52-5 ]
YieldReaction ConditionsOperation in experiment
89% With dmap; copper(l) iodide; In methanol; at 20℃; for 4h; General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 molpercent), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products. N-(2,4,6-Trimethylphenyl)-S,S-methylphenylsulfoximine (3aa) Yield: 235 mg (89percent); pale yellow oil; cc: 20percent EtOAc/hexane; Rf = 0.25. IR (KBr, film): 1449, 1232, 1221, 749 cm-1. 1H NMR (500 MHz, CDCl3): = 8.14 (d, J = 7.9 Hz, 2 Harom), 7.59 (m, 3 Harom), 6.84 (s, 2 Harom), 3.02 (s, 3 H, CH3), 2.33 (s, 6 H, 2 CH3), 2.23 (s, 3 H, CH3). 13C NMR (125 MHz, CDCl3): = 141.4, 138.0, 133.9, 133.1, 132.5, 129.3, 129.2, 128.0, 43.3, 20.8, 20.1. HRMS (ESI-TOF): m/z [M + H]+ calcd for C16H20NOS: 274.1226; found: 274.1257.
  • 73
  • [ 6783-05-7 ]
  • [ 4381-25-3 ]
  • N-phenylethenyl-S,S-methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With dmap; copper(l) iodide In methanol at 20℃; for 0.75h; N-Arylation of Sulfoximines with Arylboronic Acids; General Procedure General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 mol%), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products.
  • 74
  • [ 23112-96-1 ]
  • [ 4381-25-3 ]
  • N-(2,6-dimethoxyphenyl)-S,S-methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; copper(l) iodide; In methanol; at 20℃; for 4h; General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 mol%), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products.
  • 75
  • [ 63139-21-9 ]
  • [ 4381-25-3 ]
  • [ 1316303-49-7 ]
YieldReaction ConditionsOperation in experiment
90% With dmap; copper(l) iodide In methanol at 20℃; for 1h; N-Arylation of Sulfoximines with Arylboronic Acids; General Procedure General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 mol%), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products.
  • 76
  • [ 98546-51-1 ]
  • [ 4381-25-3 ]
  • N-(4-methylthiophenyl)-S,S-methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With dmap; copper(l) iodide In methanol at 20℃; for 1.5h; N-Arylation of Sulfoximines with Arylboronic Acids; General Procedure General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 mol%), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products.
  • 77
  • [ 4381-25-3 ]
  • [ 67492-50-6 ]
  • N-(3,5-dichlorophenyl)-S,S-methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With dmap; copper(l) iodide; In methanol; at 20℃; for 2h; General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 molpercent), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products.
  • 78
  • [ 2156-04-9 ]
  • [ 4381-25-3 ]
  • N-(4-vinylphenyl)-S,S-methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With dmap; copper(l) iodide; In methanol; at 20℃; for 1h; General procedure: A mixture of the respective sulfoximine (150 mg, 1 equiv, for 3aa,3ba, 3ja, 3ab, 3ac, 3ad-3nd, 3ae-3au, 3me and 3mk) or (200 mg, 1 equiv, for 3ca-3ia and 3ka), CuI (10 mol%), and 4-DMAP (1 equiv) was stirred in MeOH (2 mL) under open air at RT for 5 min. The appropriate arylboronic acid or arylboronic acid surrogate or vinylboronic acid (1.5 equiv) was added to the reaction mixture and allowed to stir at RT. The progress of reaction was monitored by TLC. After completion, the reaction mixture was diluted with CH2Cl2 and washed with distilled water, aq NaHCO3, and brine. The organic layer was dried (anhyd Na2SO4), filtered, and evaporated on a rotary evaporator. The crude product was purified by silica gel column chromatography using EtOAc/hexane as an eluent to obtain the desired products.
  • 79
  • [ 635-26-7 ]
  • [ 4381-25-3 ]
  • rac-N-[(2-methyl)-phenyl]-S-phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With oxygen; potassium acetate; copper(I) bromide; In acetone; at 20℃; for 12h;Schlenk technique; General procedure: Under the oxygen atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 1 (0.5 mmo), arylhydrazine chloride (2.0 equiv.), Cu(OAc)2 (20 mol%), KOAc (2.0 equiv.) in dry acetone (4.0 mL). Then the mixture was allowed to stir at room temperature for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexaneand ethyl acetate (2:1) as eluent to give the corresponding arylated products 3 or 5 (Rf = ca.0.3 otherwise noted).
  • 80
  • [ 36600-66-5 ]
  • [ 4381-25-3 ]
  • N-[(4-(tert-butyl)phenyl)]-S-methyl-S-phenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With oxygen; potassium acetate; copper(I) bromide; In acetone; at 20℃; for 12h;Schlenk technique; General procedure: Under the oxygen atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 1 (0.5 mmo), arylhydrazine chloride (2.0 equiv.), Cu(OAc)2 (20 mol%), KOAc (2.0 equiv.) in dry acetone (4.0 mL). Then the mixture was allowed to stir at room temperature for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexaneand ethyl acetate (2:1) as eluent to give the corresponding arylated products 3 or 5 (Rf = ca.0.3 otherwise noted).
  • 81
  • [ 41052-75-9 ]
  • [ 4381-25-3 ]
  • rac-N-[(2-chloro)-phenyl]-S-phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With oxygen; potassium acetate; copper(I) bromide; In acetone; at 20℃; for 12h;Schlenk technique; General procedure: Under the oxygen atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 1 (0.5 mmo), arylhydrazine chloride (2.0 equiv.), Cu(OAc)2 (20 mol%), KOAc (2.0 equiv.) in dry acetone (4.0 mL). Then the mixture was allowed to stir at room temperature for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexaneand ethyl acetate (2:1) as eluent to give the corresponding arylated products 3 or 5 (Rf = ca.0.3 otherwise noted).
  • 82
  • [ 622-88-8 ]
  • [ 4381-25-3 ]
  • rac-N-[(4-bromo)phenyl]-S-phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With oxygen; potassium acetate; copper(I) bromide In acetone at 20℃; for 12h; Schlenk technique; 4. General procedure towards N-aryl sulfoximines 3 General procedure: Under the oxygen atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 1 (0.5 mmo), arylhydrazine chloride (2.0 equiv.), Cu(OAc)2 (20 mol%), KOAc (2.0 equiv.) in dry acetone (4.0 mL). Then the mixture was allowed to stir at room temperature for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexaneand ethyl acetate (2:1) as eluent to give the corresponding arylated products 3 or 5 (Rf = ca.0.3 otherwise noted).
  • 83
  • [ 62830-55-1 ]
  • [ 4381-25-3 ]
  • N-(4-iodophenyl)-S-methyl-S-phenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With oxygen; potassium acetate; copper(I) bromide; In acetone; at 20℃; for 12h;Schlenk technique; General procedure: Under the oxygen atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 1 (0.5 mmo), arylhydrazine chloride (2.0 equiv.), Cu(OAc)2 (20 mol%), KOAc (2.0 equiv.) in dry acetone (4.0 mL). Then the mixture was allowed to stir at room temperature for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexaneand ethyl acetate (2:1) as eluent to give the corresponding arylated products 3 or 5 (Rf = ca.0.3 otherwise noted).
  • 84
  • [ 2923-56-0 ]
  • [ 4381-25-3 ]
  • (±)-methyl(phenyl)((4-(trifluoromethyl)phenyl)imino)-λ6-sulfanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With oxygen; potassium acetate; copper(I) bromide; In acetone; at 20℃; for 12h;Schlenk technique; General procedure: Under the oxygen atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 1 (0.5 mmo), arylhydrazine chloride (2.0 equiv.), Cu(OAc)2 (20 mol%), KOAc (2.0 equiv.) in dry acetone (4.0 mL). Then the mixture was allowed to stir at room temperature for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexaneand ethyl acetate (2:1) as eluent to give the corresponding arylated products 3 or 5 (Rf = ca.0.3 otherwise noted).
  • 85
  • [ 2243-58-5 ]
  • [ 4381-25-3 ]
  • N-(2-naphthyl)-S-phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With oxygen; potassium acetate; copper(I) bromide; In acetone; at 20℃; for 12h;Schlenk technique; General procedure: Under the oxygen atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 1 (0.5 mmo), arylhydrazine chloride (2.0 equiv.), Cu(OAc)2 (20 mol%), KOAc (2.0 equiv.) in dry acetone (4.0 mL). Then the mixture was allowed to stir at room temperature for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexaneand ethyl acetate (2:1) as eluent to give the corresponding arylated products 3 or 5 (Rf = ca.0.3 otherwise noted).
  • 86
  • [ 13361-30-3 ]
  • [ 4381-25-3 ]
  • isopropyl 2-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]amino}-2-oxoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium dihydrogenphosphate; methoxy(mesyloxy)iodobenzene In acetonitrile at 20℃; for 30h; Sealed tube;
  • 87
  • [ 13361-32-5 ]
  • [ 4381-25-3 ]
  • allyl 2-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]amino}-2-oxoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium dihydrogenphosphate; methoxy(mesyloxy)iodobenzene In acetonitrile at 20℃; for 30h; Sealed tube;
  • 88
  • [ 100-42-5 ]
  • [ 6911-51-9 ]
  • [ 4381-25-3 ]
  • methyl(phenyl)((1-phenyl-2-(thiophen-2-ylthio)ethyl)imino)-λ6-sulfanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With dipotassium peroxodisulfate; tetra-(n-butyl)ammonium iodide In ethyl acetate at 20℃; for 20h; Irradiation; Green chemistry; chemoselective reaction;
  • 89
  • [ 4381-25-3 ]
  • [ 116707-09-6 ]
  • [ 1426922-68-0 ]
  • 90
  • [ 6026-75-1 ]
  • [ 4381-25-3 ]
  • [ 1377585-43-7 ]
YieldReaction ConditionsOperation in experiment
62% With N-Bromosuccinimide In tetrachloromethane at 20℃; for 17h; Irradiation;
  • 91
  • [ 57102-98-4 ]
  • [ 4381-25-3 ]
  • N-[9-ethyl-9H-carbazole-3-carbothioyl]-S-methyl-S-phenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 12 h / 0 - 20 °C / Schlenk technique 2: Lawessons reagent / toluene / 8 h / 110 °C / Schlenk technique
  • 92
  • [ 644-32-6 ]
  • [ 4381-25-3 ]
  • [ 54090-90-3 ]
YieldReaction ConditionsOperation in experiment
74% With 9-mesityl-10-methylacridin-10-ium tetrafluoroborate In tetrahydrofuran at 20℃; for 12h; Irradiation; Green chemistry;
  • 93
  • [ 644-32-6 ]
  • [ 4381-25-3 ]
  • [ 507-09-5 ]
  • [ 54090-90-3 ]
  • N-acetyl methylphenylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 43% 2: 35% With 9-mesityl-10-methylacridin-10-ium tetrafluoroborate In tetrahydrofuran at 20℃; for 12h; Irradiation; Green chemistry;
Same Skeleton Products
Historical Records

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[ 4381-25-3 ]

Chemical Structure| 83730-53-4

A215764[ 83730-53-4 ]

(2S)-2-Amino-4-(butylsulfonimidoyl)butanoic acid

Reason: Sulfoximine, Bioisosteric