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[ CAS No. 15398-96-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 15398-96-6
Chemical Structure| 15398-96-6
Chemical Structure| 15398-96-6
Structure of 15398-96-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 15398-96-6 ]

CAS No. :15398-96-6 MDL No. :N/A
Formula : C7H5F3O2S2 Boiling Point : -
Linear Structure Formula :- InChI Key :VJKJRLIFMWSBNO-UHFFFAOYSA-N
M.W : 242.24 Pubchem ID :70521554
Synonyms :

Calculated chemistry of [ 15398-96-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.32
TPSA : 67.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.81
Log Po/w (WLOGP) : 4.97
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 2.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.142 mg/ml ; 0.000587 mol/l
Class : Soluble
Log S (Ali) : -3.89
Solubility : 0.0311 mg/ml ; 0.000128 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.33
Solubility : 0.114 mg/ml ; 0.000472 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.34

Safety of [ 15398-96-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15398-96-6 ]

* 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 [ 15398-96-6 ]

[ 15398-96-6 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 1045821-71-3 ]
  • [ 62-53-3 ]
  • [ 15398-96-6 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: aniline With tert.-butylnitrite; boron trifluoride diethyl etherate In acetonitrile Cooling with ice; Stage #2: N-[(trifluoromethyl)sulfanyl]aniline With 1-aminomorpholine; bismuth(III) chloride; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In acetonitrile at 80 - 100℃; 1 Example 1 Air atmosphere,In the ice water bath1.8 parts by weightTert-butyl nitriteAnd 1.5 parts by weight of aniline was droppedAnd 1.8 parts by weight of boron trifluoride diethyl ether in acetonitrile,Magnetic stirrer for 2-3 minutes.then,To the reaction system0.6 part by weight of DABSO (DABCO · (SO2) 2) was added,1.0 part by weight of N-aminomorpholine,1.3 parts by weight of N-trifluoromethylthioanilineAnd 2.0 parts by weight of bismuth chloride.The temperature of the system was raised to 80-100 ,The reaction was continued for 6-12 hours,The reaction was monitored by TLC until complete reaction.The reaction solution was extracted with ethyl acetate at the time of post-Anhydrous Na2SO4 dry,The purified product aryl trifluoromethanesulfonate 2a was isolated by flash column chromatography using a decompression solvent.Isolated yield: 74%;
  • 2
  • [ 1045821-71-3 ]
  • [ 873-55-2 ]
  • [ 15398-96-6 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; General procedure for the synthesis of compound 3 General procedure: Sulfonyl chloride 1 (0.2 mmol) was added into a solution of Na2SO3 (2.0 equiv) and NaHCO3 (2.0 equiv) in H2O (1.0 mL). The mixture was stirred at 80°C for 4h. After evaporation of water, PhNHSCF3 2 (0.3 mmol), 4-methylbenzenesulfonic acid (0.5mmol) and DCE (2 ml) were added. The mixture was stirred at room temperature. After completion of the reaction as indicated by TLC, the reaction mixture was filtered by sand core funnel with silica gel and washed by CH2Cl2. The volatiles were removed and the residue was purified by flash column chromatography (SiO2) to provide the final products 3. S-trifluoromethyl benzenesulfonothioate (3a). 1H NMR (400 MHz, CDCl3) δ 7.60-7.63 (m, 2H), 7.72-7.76 (m, 1H), 8.01 (d, J = 7.6Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 127.3 (q, J = 311.4 Hz), 127.6, 129.7, 135.2,144.6; 19F NMR (378 MHz, CDCl3) δ -38.5 (s); HRMS (EI) calcd for C7H5F3O2S2+:241.9678 (M+), found: 241.9685
  • 3
  • [ 57187-83-4 ]
  • [ 15398-96-6 ]
  • C21H21F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 4
  • [ 15398-96-6 ]
  • C15H18O [ No CAS ]
  • C22H23F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 5
  • [ 15398-96-6 ]
  • C20H20O [ No CAS ]
  • C27H25F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 6
  • [ 15398-96-6 ]
  • C14H15FO [ No CAS ]
  • C21H20F4O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 7
  • [ 15398-96-6 ]
  • C15H18O [ No CAS ]
  • C22H23F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 8
  • [ 15398-96-6 ]
  • [ 107711-51-3 ]
  • C15H17F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 9
  • [ 15398-96-6 ]
  • [ 132330-44-0 ]
  • C22H24F3NO4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 10
  • [ 15398-96-6 ]
  • [ 133788-02-0 ]
  • C22H27F3O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 11
  • [ 1403588-59-9 ]
  • [ 15398-96-6 ]
  • C16H19F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 12
  • [ 15398-96-6 ]
  • [ 147048-26-8 ]
  • C23H26F3NO4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; Irradiation; regioselective reaction;
  • 13
  • [ 15398-96-6 ]
  • [ 536-74-3 ]
  • C15H11F3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 14
  • [ 766-96-1 ]
  • [ 15398-96-6 ]
  • C15H10BrF3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 15
  • [ 766-98-3 ]
  • [ 15398-96-6 ]
  • C15H10F4O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 16
  • [ 3034-86-4 ]
  • [ 15398-96-6 ]
  • C17H13F3O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 17
  • [ 15398-96-6 ]
  • [ 768-60-5 ]
  • C16H13F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 18
  • [ 15398-96-6 ]
  • [ 766-97-2 ]
  • C16H13F3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 19
  • [ 10401-11-3 ]
  • [ 15398-96-6 ]
  • C15H11F3O3S2 [ No CAS ]
  • 20
  • [ 766-82-5 ]
  • [ 15398-96-6 ]
  • C16H13F3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 21
  • [ 766-47-2 ]
  • [ 15398-96-6 ]
  • C16H13F3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 22
  • [ 15398-96-6 ]
  • [ 765914-04-3 ]
  • C24H18F3NO4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 23
  • [ 67237-53-0 ]
  • [ 15398-96-6 ]
  • C13H9F3O2S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 24
  • [ 930-51-8 ]
  • [ 15398-96-6 ]
  • C14H15F3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 25
  • [ 673-32-5 ]
  • [ 15398-96-6 ]
  • C16H13F3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 26
  • [ 2749-94-2 ]
  • [ 15398-96-6 ]
  • C16H13F3O2S2 [ No CAS ]
  • C17H15F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; Overall yield = 74%; regioselective reaction;
  • 27
  • [ 15398-96-6 ]
  • [ 131558-77-5 ]
  • C17H15F3O3S2 [ No CAS ]
  • C17H15F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; Overall yield = 77%; regioselective reaction;
  • 28
  • [ 15398-96-6 ]
  • [ 131558-77-5 ]
  • C20H21F3O3S2 [ No CAS ]
  • C20H21F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; Overall yield = 77%; regioselective reaction;
  • 29
  • [ 15398-96-6 ]
  • [ 188640-59-7 ]
  • C24H26F3NO6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 30
  • [ 15398-96-6 ]
  • C13H14O3 [ No CAS ]
  • C20H19F3O5S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 31
  • [ 15398-96-6 ]
  • (8R,9S,13S,14S)-3-ethynyl-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one (8R,9S,13S,14S)-3-ethynyl-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]p [ No CAS ]
  • C27H27F3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris(2,2'-bipyridyl)ruthenium dichloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 20℃; for 6h; Irradiation; Inert atmosphere; regioselective reaction;
  • 32
  • [ 15398-96-6 ]
  • N-(allylsulfonyl)-N-(4-methylpentyl)benzamide [ No CAS ]
  • N-(4-methyl-4-((trifluoromethyl)thio)pentyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dilauryl peroxide In chloroform at 80℃; for 24h; Inert atmosphere;
  • 33
  • [ 15398-96-6 ]
  • N-(allylsulfonyl)-N-(3-cyclohexylpropyl)benzamide [ No CAS ]
  • N-(3-(1-((trifluoromethyl)thio)cyclohexyl)propyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With dilauryl peroxide In chloroform at 80℃; for 24h; Inert atmosphere; Schlenk technique;
  • 34
  • [ 15398-96-6 ]
  • N-(allylsulfonyl)-N-(2-methoxyethyl)benzamide [ No CAS ]
  • N-(2-(((trifluoromethyl)thio)methoxy)ethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With dilauryl peroxide In chloroform at 80℃; for 24h; Inert atmosphere; Schlenk technique;
  • 35
  • [ 1140923-61-0 ]
  • [ 15398-96-6 ]
  • (4-(4-iodophenoxy)butan-2-yl)(trifluoromethyl)sulfane [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 1 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 36
  • [ 15398-96-6 ]
  • [ 105534-98-3 ]
  • 4-(3-((trifluoromethyl)thio)butoxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 2 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 37
  • [ 15398-96-6 ]
  • [ 110589-31-6 ]
  • 1-(4-(3-((trifluoromethyl)thio)butoxy)phenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 3 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 38
  • [ 15398-96-6 ]
  • [ 132995-66-5 ]
  • ethyl 4-(3-((trifluoromethyl)thio)butoxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 4 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 39
  • hex-5-en-1-yl 4-chlorobenzoate [ No CAS ]
  • [ 15398-96-6 ]
  • 5-((trifluoromethyl)thio)hexyl 4-chlorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 5 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 40
  • [ 1352390-87-4 ]
  • [ 15398-96-6 ]
  • 5-((trifluoromethyl)thio)hexyl 4-bromobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 6 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 41
  • [ 1344711-07-4 ]
  • [ 15398-96-6 ]
  • 5-((trifluoromethyl)thio)hexyl furan-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 11 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 42
  • hex-5-en-1-yl thiophene-2-carboxylate [ No CAS ]
  • [ 15398-96-6 ]
  • 5-((trifluoromethyl)thio)hexyl thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 12 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 43
  • [ 15398-96-6 ]
  • [ 77257-06-8 ]
  • (13S)-13,17-dimethyl-17-((trifluoromethyl)thio)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 19 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 44
  • hex-5-en-1-yl 4-methoxybenzoate [ No CAS ]
  • [ 15398-96-6 ]
  • 5-((trifluoromethyl)thio)hexyl 4-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 7 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 45
  • hex-5-en-1-yl 4-fluorobenzoate [ No CAS ]
  • [ 15398-96-6 ]
  • 5-((trifluoromethyl)thio)hexyl 4-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 8 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 46
  • [ 1454661-70-1 ]
  • [ 15398-96-6 ]
  • 4-((trifluoromethyl)thio)pentyl 4-(trifluoromethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 9 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 47
  • [ 15398-96-6 ]
  • C13H16O4S [ No CAS ]
  • 4-((trifluoromethyl)thio)pentyl 4-(methylsulfonyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 10 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 48
  • [ 19300-54-0 ]
  • [ 15398-96-6 ]
  • 4-((trifluoromethyl)thio)pentyl 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 13 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 49
  • [ 15398-96-6 ]
  • C11H13ClO3S [ No CAS ]
  • 4-((trifluoromethyl)thio)pentyl 4-chlorobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 14 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 50
  • [ 15398-96-6 ]
  • C11H15NO2 [ No CAS ]
  • 3-methyl-3-((trifluoromethyl)thio)butyl 1-methyl-1H-pyrrole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 15 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 51
  • [ 1454661-78-9 ]
  • [ 15398-96-6 ]
  • 3-methyl-3-((trifluoromethyl)thio)butyl 4-cyanobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 16 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 52
  • [ 15398-96-6 ]
  • C14H19NO2 [ No CAS ]
  • C15H20F3NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 17 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 53
  • [ 15398-96-6 ]
  • C21H21NO4S [ No CAS ]
  • 3-methyl-3-((trifluoromethyl)thio)butyl 2-(1-(phenylsulfonyl)-1H-indol-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction; 18 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 54
  • [ 50487-72-4 ]
  • [ 15398-96-6 ]
  • 3-methyl-1-tosyl-4-(((trifluoromethyl)thio)methyl)pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tert.-butylhydroperoxide; 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetic acid potassium salt; phenylsilane; cobalt(II) diacetate tetrahydrate In ethanol at 28℃; for 6h; Schlenk technique; Inert atmosphere; 21 1.4 General procedure for hydrogen-trifluoromethylthiolation of olefins General procedure: Co(OAc)2·4H2O (7.5 mg, 6.0 mol%), ligand L1 (15.0 mg, 6.0 mol%) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an argon atmosphere. 2.5 mL of ethanol was added into the Schlenk tube. The solution was stirred at 28 °C for 15 min. Then, tBuOOH (27.5 μL, 0.55 M in decene, 30.0 mol%) was added under an argon atmosphere, The solution was stirred at 28 °C for another 15 min. At last, olefins (0.5 mmol), PhSO2SCF3 (242 mg, 1.00 mmol, 2.00 equiv), PhSiH3 (87 mg, 0.80 mmol, 1.6 equiv) were added. The reaction was stirred at 28 °C for 6 h. 10 mL of distilled water and 40 mL of Et2O were added and the organic phase was separated and washed with 25 mL of saturated brines twice. The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The product was purified by flash chromatography on silica gel.
  • 55
  • [ 15398-96-6 ]
  • 2-(3-(allylsulfonyl)hexyl)isoindoline-1,3-dione [ No CAS ]
  • 2-(3-((trifluoromethyl)thio)hexyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With 2,2'-azobis(isobutyronitrile) In chloroform at 85℃; for 48h; Inert atmosphere; Schlenk technique;
  • 56
  • [ 15398-96-6 ]
  • (3S,4aS,5aR,6aS,6bS,9R,9aR,11aS,11bR)-3-(allylsulfonyl)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxirene [ No CAS ]
  • (4aS,5aR,6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)-3-((trifluoromethyl)thio)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxirene [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With 2,2'-azobis(isobutyronitrile) In chloroform at 85℃; for 48h; Inert atmosphere; Schlenk technique; diastereoselective reaction;
  • 57
  • [ 15398-96-6 ]
  • 2-(3-(allylsulfonyl)-3-methylbutyl)isoindoline-1,3-dione [ No CAS ]
  • 2-(3-methyl-3-((trifluoromethyl)thio)butyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 2,2'-azobis(isobutyronitrile) In chloroform at 85℃; for 48h; Inert atmosphere; Schlenk technique;
  • 58
  • [ 15398-96-6 ]
  • [ CAS Unavailable ]
  • [ 1927969-10-5 ]
YieldReaction ConditionsOperation in experiment
7 %Spectr. With iron(III) chloride; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h;
  • 59
  • 2-acetyl-1-((trifluoromethyl)thio)-1,2-dihydro-3H-1λ3-benzo[d][1,2]iodazol-3-one [ No CAS ]
  • [ 873-55-2 ]
  • [ 15398-96-6 ]
YieldReaction ConditionsOperation in experiment
79% With acetic acid at 20℃; for 0.166667h; Inert atmosphere;
  • 60
  • [ 100-42-5 ]
  • [ 15398-96-6 ]
  • C10H10BrNO2S2 [ No CAS ]
  • C19H18F3NS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere; Irradiation;
  • 61
  • [ 300-57-2 ]
  • [ 15398-96-6 ]
  • C16H15F3O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 9-(2-mesityl)-10-methylacridinium perchlorate at 20℃; for 18h; Irradiation;
  • 62
  • [ 15398-96-6 ]
  • 2-(4-((3-(4-methoxy-3-(pentyloxy)phenyl)-2-oxotetrahydropyrimidin-1(2H)-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)-N,N-dimethylacetamide [ No CAS ]
  • 2-(4-((3-(4-methoxy-3-(pentyloxy)phenyl)-2-oxotetrahydropyrimidin-1(2H)-yl)methyl)-3-((trifluoromethyl)thio)-1H-pyrrolo[2,3-b]pyridin-1-yl)-N,N-dimethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; Irradiation; 22 Following a modified protocol reported by Li. et al. (Chem. Sci., 2018, 9, 5781): A 20 -mL vial is charged with 2-(4-((3-(4-methoxy-3-(pentyloxy)phenyl)-2- oxotetrahydropyrimidin-1(2H)-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)-N,N- dimethylacetamide (150 mg, 0.30 mmol) and S-(trifluoromethyl) benzenesulfonothioate (143 mg, 0.59 mmol). The vial is evacuated and purged with argon three times. A solution of tetrabutylammonium iodide (22 mg, 0.06 mmol) in degassed, anhydrous acetonitrile (3 mL) is added to the vial. The reaction is stirred at room temperature overnight while being irradiated by a household compact fluorescent lightbulb (CFL). The reaction is diluted with ethyl acetate, then filtered through CELITE. The filter cake is thoroughly washed with ethyl acetate. The filtered solution is concentrated in vacuo. Purification by column chromatography over reversed-phase C18 silica gel afforded 2-(4-((3-(4-methoxy-3- (pentyloxy)phenyl)-2-oxotetrahydropyrimidin-1(2H)-yl)methyl)-3-((trifluoromethyl)thio)- 1H-pyrrolo[2,3-b]pyridin-1-yl)-N,N-dimethylacetamide.
  • 63
  • [ 15398-96-6 ]
  • [ 4748-78-1 ]
  • S-(trifluoromethyl)-4-ethylbenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 64
  • [ 15398-96-6 ]
  • [ 122-03-2 ]
  • S-(trifluoromethyl)-4-isopropylbenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 65
  • [ 939-97-9 ]
  • [ 15398-96-6 ]
  • (S-(trifluoromethyl)-4-(tert-butyl)benzothioate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 66
  • [ 40150-98-9 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl)-4-isobutylbenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 67
  • [ 15398-96-6 ]
  • [ 459-57-4 ]
  • S-(trifluoromethyl) 4-fluorobenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 68
  • [ 15398-96-6 ]
  • [ 104-88-1 ]
  • S-(trifluoromethyl) 4-chlorobenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 69
  • [ 15398-96-6 ]
  • [ 1122-91-4 ]
  • S-(trifluoromethyl) 4-bromobenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 70
  • [ 15398-96-6 ]
  • [ 15164-44-0 ]
  • S-(trifluoromethyl)-4-iodobenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 71
  • [ 15398-96-6 ]
  • [ 105-07-7 ]
  • S-(trifluoromethyl) 4-cyanobenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 72
  • [ 455-19-6 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl) 4-(trifluoromethyl)benzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 73
  • [ 15398-96-6 ]
  • [ 1571-08-0 ]
  • methyl 4-(((trifluoromethyl)thio)carbonyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 74
  • [ 15398-96-6 ]
  • [ 80459-48-9 ]
  • S-(trifluoromethyl) 4-(tosyloxy)benzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 75
  • [ 15398-96-6 ]
  • [ 620-23-5 ]
  • S-(trifluoromethyl) 3-methylbenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 76
  • [ 15398-96-6 ]
  • [ 456-48-4 ]
  • S-(trifluoromethyl) 3-fluorobenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 77
  • [ 15398-96-6 ]
  • [ 529-20-4 ]
  • S-(trifluoromethyl)-2-methylbenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 78
  • [ 15398-96-6 ]
  • [ 120-14-9 ]
  • S-(trifluoromethyl)-3,4-dimethoxybenzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 79
  • [ 15398-96-6 ]
  • [ 66-77-3 ]
  • S-(trifluoromethyl) naphthalene-1-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 80
  • [ 15398-96-6 ]
  • [ 66-99-9 ]
  • S-(trifluoromethyl) naphthalene-2-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 81
  • [ 50562-79-3 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl)-1-tosyl-1H-indole-3-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 82
  • [ 5381-20-4 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl)-benzo[b]thiophene-3-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 83
  • [ 124-13-0 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl) octanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 84
  • [ 112-31-2 ]
  • [ 15398-96-6 ]
  • C11H19F3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 85
  • [ 112-54-9 ]
  • [ 15398-96-6 ]
  • (S-(trifluoromethyl)dodecanethioate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 86
  • [ 124-25-4 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl) tetradecanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 87
  • [ 5435-64-3 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl)-3,5,5-trimethylhexanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 88
  • [ 3913-81-3 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl)-(E)-dec-2-enethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 89
  • [ 23727-16-4 ]
  • [ 15398-96-6 ]
  • S-(trifluoromethyl)-(1S,5R)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 90
  • [ 15398-96-6 ]
  • 4-formylphenyl 4-(N,N-dipropylsulfamoyl)benzoate [ No CAS ]
  • 4-(((trifluoromethyl)thio)carbonyl)phenyl-4-(N,N-dipropylsulfamoyl) benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 91
  • [ 15398-96-6 ]
  • 4-formylphenyl 2-(4-isobutylphenyl)propanoate [ No CAS ]
  • 4-(((trifluoromethyl)thio)carbonyl)phenyl-2-(4-isobutylphenyl) propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 92
  • [ 15398-96-6 ]
  • C34H52O2 [ No CAS ]
  • S-(trifluoromethyl)4-(((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy) benzothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;
  • 93
  • [ 15398-96-6 ]
  • (3aR)-(+)-sclareolide [ No CAS ]
  • (3aR,5aS,8S,9aS,9bR)-3a,6,6,9a-tetramethyl-8-[(trifluoromethyl)thio]decahydronaphtho[2,1-b]furan-2(3aH)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With 1,10-Phenanthroline; copper(l) cyanide; N-(tert-butyl)-N-fluoro-3,5-bis(trifluoromethyl)benzenesulfonamide In 1,2-dichloro-ethane at 60℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;
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