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[ CAS No. 1774-35-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1774-35-2
Chemical Structure| 1774-35-2
Chemical Structure| 1774-35-2
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Product Details of [ 1774-35-2 ]

CAS No. :1774-35-2 MDL No. :MFCD00008546
Formula : C14H14OS Boiling Point : -
Linear Structure Formula :- InChI Key :MJWNJEJCQHNDNM-UHFFFAOYSA-N
M.W : 230.33 Pubchem ID :15680
Synonyms :

Calculated chemistry of [ 1774-35-2 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 67.63
TPSA : 36.28 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 3.43
Log Po/w (WLOGP) : 4.34
Log Po/w (MLOGP) : 3.8
Log Po/w (SILICOS-IT) : 3.25
Consensus Log Po/w : 3.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.85
Solubility : 0.0324 mg/ml ; 0.000141 mol/l
Class : Soluble
Log S (Ali) : -3.87
Solubility : 0.0309 mg/ml ; 0.000134 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.71
Solubility : 0.000445 mg/ml ; 0.00000193 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 1774-35-2 ]

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

Application In Synthesis of [ 1774-35-2 ]

* 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 [ 1774-35-2 ]

[ 1774-35-2 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 1774-35-2 ]
  • [ 1207-15-4 ]
YieldReaction ConditionsOperation in experiment
85% With ruthenium(III) chloride trihydrate; silver carbonate; trifluoroacetic acid at 140℃; for 20h; Inert atmosphere;
With phenyl sodium; benzene at 80 - 90℃; im Rohr;
  • 2
  • [ 1774-35-2 ]
  • [ 599-66-6 ]
Reference: [1]Russian Journal of Organic Chemistry,1995,vol. 31,p. 1520 - 1525
    Zhurnal Organicheskoi Khimii,1995,vol. 31,p. 1692 - 1697
[2]Journal of Organic Chemistry,1983,vol. 48,p. 3585 - 3587
[3]Journal of Organic Chemistry,2007,vol. 72,p. 5847 - 5850
[4]Canadian Journal of Chemistry,1984,vol. 62,p. 1164 - 1168
[5]Journal of the American Chemical Society,1946,vol. 68,p. 973,974, 976, 2671
    Journal of the American Chemical Society,1947,vol. 69,p. 644,2310
[6]Magnetic Resonance in Chemistry,1989,vol. 27,p. 360 - 367
[7]Journal of the Chemical Society. Chemical communications,1982,p. 1352 - 1353
[8]Journal of the American Chemical Society,1981,vol. 103,p. 3832 - 3837
[9]Canadian Journal of Chemistry,1987,vol. 65,p. 2421 - 2424
[10]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1981,vol. 20,p. 505 - 506
[11]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1986,vol. 25,p. 678 - 680
[12]Journal of the Indian Chemical Society,1992,vol. 69,p. 819 - 821
[13]Journal of Organic Chemistry,1993,vol. 58,p. 5055 - 5059
[14]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1989,vol. 28,p. 250 - 252
[15]Tetrahedron,2001,vol. 57,p. 1369 - 1374
[16]Journal of Chemical Research, Miniprint,2000,p. 1118 - 1133
[17]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2005,vol. 44,p. 71 - 75
[18]Journal of the Indian Chemical Society,2007,vol. 84,p. 679 - 682
  • 3
  • [ 108-88-3 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
93% With thionyl chloride In dichloromethane at 20℃; for 1.3h; Inert atmosphere;
92% With thionyl chloride; trifluorormethanesulfonic acid at 20℃; for 24h;
86% With thionyl chloride; sodium perchlorate In tetrahydrofuran at 20℃; for 2h;
85% With thionyl chloride; water at 20℃; for 0.0833333h;
95 % Chromat. With antimony pentafluoride; fluorosulphonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane
With aluminium trichloride; thionyl chloride
95 % Chromat. With antimony pentafluoride; fluorosulphonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) -78 deg C 2.) -30 deg C 3.) 0 deg C, 1.5 h;
With thionyl chloride
95 %Chromat. With thionyl chloride; bromobenzene In dichloromethane at 20℃; for 1.5h; Inert atmosphere; chemoselective reaction;
95 %Chromat. With thionyl chloride; nitrobenzene In dichloromethane at 20℃; for 1.5h; Inert atmosphere; chemoselective reaction;
With thionyl chloride; trifluorormethanesulfonic acid Inert atmosphere;

  • 4
  • [ 4294-57-9 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
80% With C9H16O7S In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; 3.4. Reaction of (R)-1,2-O-Isopropylidene-3,5-O-Sulfinyl- -d-Glucofuranose (+)-(R)-4 withPhenylmagnesium Bromide A solution of (+)-(R)-4 (0.133 g, 0.5 mmol) in of THF (5 mL) was cooled to 0 C and treated with a solution of freshly prepared phenylmagnesium bromide (1.5 mmol) in THF (10 mL). The progressof the reaction was monitored with TLC and after disappearance of the substrate (1.5 h) themixture was treated with aqueous, saturated ammonium chloride solution (7 mL) and extractedwith chloroform (4 10 mL). The combined organic phase was dried over magnesium sulfate andevaporated. The residue was separated on a silica gel column using DCM: ethyl acetate 2:1 and, nally,with ethyl acetate as eluents for diphenyl sulfoxide 9b (88 mg, 89%) m.p. 69-71 C; 1H NMR (CDCl3): = 7.22-7.36 (m, 6H), 7.47-7.62 (m, 4H) (these data are in accordance with literature data [35-37])and 1,2-O-isopropylidene--d-glucofuranose 13 (71 mg, 65% []D = 11.2 (c = 1.2, H2O- this valueis in accordance with literature data [38]). Substrate (+)-(R)-4 was not detected. A similar reaction of (+)-(R)-4 (0.133 g, 0.5 mmol) with p-toluenemagnesium bromide (1.5 mmol) aorded di-p-tolylsulfoxide 9c (92 mg, 80%) m.p. 92-94 C; 1H NMR (CDCl3): = 2.35, 7.25, and 7.52 (AB system,J = 7.2 Hz, 4H) (these data are in accordance with literature data [39]).
With diethyl ether; sulfur dioxide anschliessendes Erwaermen mit wss. Saeure;
With 1,1'-binaphthyl-2,2'-diyl sulfite
  • 5
  • [ 75-80-9 ]
  • [ 1774-35-2 ]
  • C14H14OS*C2H3Br3O [ No CAS ]
  • 7
  • [ 620-94-0 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
96% With o-iodosobenzoic acid In water; acetic acid for 2h;
95% With palladium; dihydrogen peroxide In methanol at 60℃; for 16h; Green chemistry; chemoselective reaction;
95% With anthraquinone-2-carbonyl immobilized onto poly(2-hydroxyethyl methacrylate); air In methanol at 20℃; for 25h; chemoselective reaction;
94% With water; N-fluorobis(benzenesulfon)imide at 20℃; for 6h; chemoselective reaction;
92% With pyridine; trichloroisocyanuric acid In dichloromethane; water; acetonitrile at 40℃; for 0.75h;
90% With tetrabutylammonium tetrafluoroborate; oxygen In dichloromethane at 20℃; for 2h; Electrochemical reaction; Green chemistry;
88% With sodium bromite In 1,4-dioxane; water for 0.25h; Ambient temperature;
83% With diethylene glycol dibutyl ether; oxygen; Langlois reagent at 20℃; for 12h; Irradiation;
71% With polymer-supported phenyliodine(III) diacetate In dichloromethane for 4h; Heating;
70% With tetrabutylammonium periodite In chloroform for 7h; Heating;
70% With poly(ethyleneglycol) dimethyl ether; oxygen at 130℃; for 16h; Green chemistry;
70% With oxygen at 130℃; for 20h;
60% With dihydrogen peroxide In methanol; dichloromethane at 20℃; for 7h;
With tri-n-butyl phosphite; oxygen; methylene blue In acetonitrile at 20℃; for 1h; Irradiation; relative reactivity (Ph2SO as a reference substrate); other reagent (Ph3S);
With phenyltrifluorodiazoethane; oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane; acetonitrile at 20℃; for 0.5h; Irradiation;
With cyclohexene sulfide; oxygen In methanol; dichloromethane at -40℃; Irradiation; methylene blue sensitizer;
With sodium periodate In methanol; water
With ((2,2'-(ethane-1,2-diylbis[(nitrilo-κN)methylidyne])bis(phenolato-κO))(2-))manganese(1+) hexafluorophosphate; dihydrogen peroxide In water; acetonitrile at 25℃;
With sodium periodate In methanol; water
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1h; Cooling with ice;
With 4C6H2O4S(2-)*4C2H3O2(1-)*Zr6O4(OH)4(12+); oxygen In methanol at 20℃; for 8h; Irradiation; 2 Example 2 Photocatalytic Oxidation of Methylphenyl Sulfide by DUT-67(Zr) to Prepare Methylphenyl Sulfoxide The prepared Zr-based metal organic framework DUT-67 (Zr) was used as a photocatalyst to oxidize methylphenyl sulfide, and 10 mg of the catalyst was weighed into the reactor, and 11.7 μL of methylphenyl sulfide was added.0.1 mL of methanol and 1.5 mL of benzotrifluoride, and oxygen is introduced under normal temperature conditions.The light source is turned on for photocatalytic reaction, and the product is detected and analyzed by gas chromatography.The light source used in the experiment was a 300 W xenon lamp.The conversion of methylphenyl sulfide and the selectivity of methylphenyl sulfoxide are shown in Figure 4.It can be seen from the figure that in the presence of a catalyst, under full-band conditions (1),The conversion of methyl phenyl sulfide reached 99% after 8 h of light, and the selectivity reached 99%.When using a filter to ensure that the incident light range is above 360 nm (2),Methylphenyl sulfide showed a conversion rate of 95% and a selectivity of 99% after 8 h of light.
50.3 %Chromat. With bis(acetylacetonate)oxovanadium; dihydrogen peroxide In methanol; water at 20℃; for 1h; Catalytic oxidation of sulfides to sulfoxides(general procedure). General procedure: To a solution of aryl sulfide 1(0.23 mmol) and 1.40 mg (2 mol %) of VO(acac)2 in5 mL of methanol, 30% H2O2 (0.46mmol) was added.The reaction mixture was stirred for 1 h at roomtemperature, filtered, and the filtrate was analyzed bygas chromatography. The retention times of sulfoxides 2are listed in Table 8.

Reference: [1]Folsom; Castrillon [Synthetic Communications, 1992, vol. 22, # 12, p. 1799 - 1806]
[2]Li, Xing; Du, Jia; Zhang, Yongli; Chang, Honghong; Gao, Wenchao; Wei, Wenlong [Organic and Biomolecular Chemistry, 2019, vol. 17, # 11, p. 3048 - 3055]
[3]Chen, Yang; Ding, Aishun; Hu, Jianhua [RSC Advances, 2020, vol. 10, # 18, p. 10661 - 10665]
[4]Cao, Zhong-Yan; Li, Xiaolong; Lu, Hao; Wang, Panpan; Wang, Shengqiang; Xu, Xiaobo; Yan, Leyu; Yang, A-Xiu [Organic and Biomolecular Chemistry, 2021, vol. 19, # 40, p. 8691 - 8695]
[5]Xiong; Huang; Zhong [Synthetic Communications, 2001, vol. 31, # 2, p. 245 - 248]
[6]Li, Jin-Heng; Li, Yang; Sun, Qing; Xue, Qi; Zhang, Ting-Ting [Organic and Biomolecular Chemistry, 2021, vol. 19, # 47, p. 10314 - 10318]
[7]Kageyama, Toshifumi; Ueno, Yoshio; Okawara, Makoto [Synthesis, 1983, # 10, p. 815 - 816]
[8]Liu, Kai-Jian; Wang, Zheng; Lu, Ling-Hui; Chen, Jin-Yang; Zeng, Fei; Lin, Ying-Wu; Cao, Zhong; Yu, Xianyong; He, Wei-Min [Green Chemistry, 2021, vol. 23, # 1, p. 496 - 500]
[9]Wang, Guo-Ping; Chen, Zhen-Chu [Synthetic Communications, 1999, vol. 29, # 16, p. 2859 - 2866]
[10]Santaniello, Enzo; Manzocchi, Ada; Farachi, Carlo [Synthesis, 1980, # 7, p. 563 - 565]
[11]Liu, Kai-Jian; Deng, Ji-Hui; Yang, Jie; Gong, Shao-Feng; Lin, Ying-Wu; He, Jun-Yi; Cao, Zhong; He, Wei-Min [Green Chemistry, 2020, vol. 22, # 2, p. 433 - 438]
[12]Tang, Lili; Du, Kejie; Yu, Bing; He, Liangnian [Chinese Chemical Letters, 2020, vol. 31, # 12, p. 2991 - 2992]
[13]Karimi, Babak; Ghoreishi-Nezhad, Maryam; Clark, James H. [Organic Letters, 2005, vol. 7, # 4, p. 625 - 628]
[14]Tsuji, Shoei; Kondo, Masaaki; Ishiguro, Katsuya; Sawaki, Yasuhiko [Journal of Organic Chemistry, 1993, vol. 58, # 19, p. 5055 - 5059]
[15]Ishiguro, Katsuya; Hirano, Yukimichi; Sawaki, Yasuhiko [Tetrahedron Letters, 1987, vol. 28, # 49, p. 6201 - 6204]
[16]Akasaka,T.; Kako,M.; Sonobe,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 494]
[17]Yoo, Byung Woo; Song, Min Suk; Park, Min Chol [Synthetic Communications, 2007, vol. 37, # 18, p. 3089 - 3093]
[18]Location in patent: experimental part Chellamani; Alhaji [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2009, vol. 48, # 3, p. 346 - 351]
[19]Location in patent: body text Yoo, Byung Woo; Min, Sang Ki [Synthetic Communications, 2011, vol. 41, # 20, p. 2993 - 2996]
[20]Wang, Binjie; Liu, Yue; Lin, Cong; Xu, Yiming; Liu, Zhanxiang; Zhang, Yuhong [Organic Letters, 2014, vol. 16, # 17, p. 4574 - 4577]
[21]Current Patent Assignee: FUZHOU UNIVERSITY - CN110194730, 2019, A Location in patent: Paragraph 0019; 0020
[22]Chen, M.; Jia, A.-Q.; Zhang, P.-Z.; Zhang, Q.-F.; Zhou, W.-Y. [Russian Journal of Organic Chemistry, 2021, vol. 57, # 5, p. 816 - 824][Zh. Org. Khim.]
  • 8
  • [ 2175-90-8 ]
  • [ 1774-35-2 ]
  • <5-(Diphenylmethylen)-1,3-cyclopentadien-1-yl>bis(4-methylphenyl)sulfonium-perchlorat [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With lithium perchlorate; trifluoroacetic anhydride In dichloromethane -10 deg C to r.t.;
With monoperchlorate; trifluoroacetic anhydride 1.) -10 deg C; Yield given. Multistep reaction;
  • 9
  • [ 77096-69-6 ]
  • [ 945-51-7 ]
  • [ 4170-71-2 ]
  • [ 67501-10-4 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
1: 21% 2: 10% With tert.-butyl lithium In tetrahydrofuran at -85℃;
1: 21% 2: 10% With tert.-butyl lithium In tetrahydrofuran at -85℃; Yield given;
  • 10
  • [ 941-55-9 ]
  • [ 1774-35-2 ]
  • [ 89279-86-7 ]
YieldReaction ConditionsOperation in experiment
34% In methanol for 8h; Heating;
  • 11
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
YieldReaction ConditionsOperation in experiment
100% With toluene-4-sulfonic acid; potassium iodide In solid at 30℃; for 30h;
99% With Carbon tetrachloride; diphenylphosphinopolystyrene for 1.5h; Heating;
99% With 2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide In toluene for 20h; Heating;
99% With thionyl chloride; triphenylphosphine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
99% With ReOBr<SUB>2</SUB>(hmpbta)(PPh<SUB>3</SUB>); phenylsilane In tetrahydrofuran for 0.2h; Reflux; chemoselective reaction;
99% With trimethylphenylsilane; ReOBr2(hmpbta)(PPh3) In tetrahydrofuran for 0.2h; Reflux;
99% With 2,2'-bis(1,3,2-benzodioxaborole) In toluene at 100℃; for 8h; Green chemistry; chemoselective reaction;
98% With hydrogenchloride; potassium iodide In chloroform at 0 - 5℃;
98% With triphenyl phosphite In acetonitrile for 1h; Heating;
98% With 2,3-dimethyl-2,3-butane diol; MoO<SUB>2</SUB>Cl<SUB>2</SUB>(DMF)<SUB>2</SUB> at 120℃; for 0.0833333h; Neat (no solvent); Microwave irradiation;
98% With Zinc di(trifluoromethanesulphonate); 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane In 1,3,5-trimethyl-benzene at 160℃; for 48h;
98% With 4-Methoxybenzyl alcohol In toluene; acetonitrile at 30℃; for 6h; Schlenk technique; Inert atmosphere; Irradiation;
97% With t-butyl bromide In chloroform for 20h; Heating;
97% With MoO<SUB>2</SUB>Cl<SUB>2</SUB>(dmf)<SUB>2</SUB> In toluene at 140℃; for 0.166667h; Microwave irradiation;
97% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; triphenylphosphine In dichloromethane at 20℃; for 24h; Inert atmosphere; Irradiation;
95% With isocyanate de chlorosulfonyle; sodium iodide In acetonitrile for 0.333333h; Heating;
95% With Methyltrichlorosilane; sodium iodide In acetonitrile for 0.333333h; Ambient temperature;
95% With sodium tetrahydridoborate; cobalt(II) chloride In ethanol for 4h; Ambient temperature;
95% With tellurium tetrachloride; sodium iodide In acetonitrile for 0.416667h; Ambient temperature;
95% With tungsten hexachloride; zinc powder In tetrahydrofuran for 0.166667h; Ambient temperature;
95% With sodium tetrahydridoborate; iodine In tetrahydrofuran at 20℃; for 0.25h;
95% With iododioxobis(triphenylphosphine)rhenium(V); phenylsilane In tetrahydrofuran at 20℃; for 0.416667h;
94% With phenylsilane; per-rhenic acid In tetrahydrofuran at 20℃; for 1.5h;
94% With gallium(0); bis(η5-cyclopentadienyl) titanium dichloride In tetrahydrofuran at 20℃; for 0.416667h; chemoselective reaction;
94% With niobium pentachloride; sodium iodide In acetonitrile at 20℃; for 0.0833333h;
94% With Zinc di(trifluoromethanesulphonate); 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In toluene at 100℃; for 18h; chemoselective reaction;
94% With dichlorobis(N,N-dimethylformamide-κO)dioxomolybdenum; glycerol at 170℃; for 17h; Green chemistry; chemoselective reaction;
94% With tantalum pentachloride; sodium iodide In acetonitrile at 20℃; for 0.05h; chemoselective reaction; 4.2. General procedure General procedure: In a 10 mL round-bottom flask, to a solution of diphenylsulfoxide (202 mg, 1.0mmol) in CH3CN (4 mL), tantalum (IV) chloride (179 mg, 0.5 mmol) and sodium iodide (300 mg, 2.0 mmol) were added at room temperature. The mixture turned dark brown almost immediately and the progress of the reaction was followed by TLC. After completion of the reaction (3 min), the reaction mixture was diluted with water and then extracted with ethyl acetate. The combined organic extracts were washed successively with 10% aq Na2S2O3 and H2O. The organic layer was separated and dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified through silicagel column chromatography (hexane:ethyl acetate = 2:1) to afford diphenylsulfide (88 mg, 95%).
93% With diphosphorus tetraiodide In dichloromethane for 0.166667h; Ambient temperature;
93% With chloro-trimethyl-silane; zinc powder In tetrahydrofuran
93% With dicarbonylbis(η-cyclopentadienyl)titanium(II) In tetrahydrofuran for 2h; Heating;
93% With titanium tetraiodide In acetonitrile at 0℃; for 0.166667h;
93% With molybdenium(VI) dioxodichloride; benzo[1,3,2]dioxaborole In tetrahydrofuran; diethyl ether at 67℃; for 0.5h;
92% With iododioxobis(triphenylphosphine)rhenium(V); benzo[1,3,2]dioxaborole In tetrahydrofuran at 20℃; for 0.0833333h;
92% With hydrogen In neat (no solvent) at 120℃; for 24h;
92% With indium powder; tantalum pentachloride In acetonitrile at 20℃; for 0.5h; Sonication; chemoselective reaction; General procedure for the deoxygenation of sulfoxides General procedure: Indium powder (229 mg, 2.0 mmol) and tantalum(V) chloride(358mg, 1.0mmol)weremixed inCH3CN(5 mL). The resultingmixture was sonicated for 0.5 h to produce a solution of the lowvalenttantalum-indium complex. Diphenyl sulfoxide (101 mg,0.5 mmol) was then added to this solution and the reactionmixturewas stirred for 3.0 h at room temperature. The progressof the reaction was followed by TLC. On completion, the solventwas removed under reduced pressure and the residue wasextracted successively with ethyl acetate, washed with water andbrine. The organic layerwas separated and dried over anhydrousNa2SO4. The crude product was purified by column chromatographyon silica gel (hexane:ethyl acetate=2:1) to afford diphenylsulfide (86mg, 92%). All of the productswere identified by comparisonof their spectroscopic data with authentic samples.
91% With indium powder; niobium pentachloride In tetrahydrofuran at 20℃; for 0.5h;
91% With hafnium tetrachloride; zinc powder In acetonitrile at 20℃; for 0.5h; 4.2. General procedure General procedure: Diphenylsulfoxide (101 mg, 0.5 mmol) and hafnium(IV) chloride (320 mg, 1.0 mmol) were mixed in CH3CN (5 mL) and zinc powder (131 mg, 2.0 mmol) was then added to this solution. The whole mixture was stirred for 3 h at room temperature and the progress of the reaction was followed by TLC. On completion, the solvent was removed under reduced pressure and the residue was extracted successively with ethyl acetate, washed with water and brine. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on a silica gel (hexane:ethyl acetate = 2:1) to afford diphenylsulfide (88 mg, 95%). All of the products were identified by comparison of their spectroscopic data with authentic samples.[34]
90% With N-Bromosuccinimide; 3-mercaptopropionic acid In acetonitrile at 20℃; for 3h;
90% With sodium iodide at 20℃; for 4h; Green chemistry; 4.1. General procedure General procedure: To a solution of a sulfoxide (1 mmol) in PEG-200 (1 ml), silica sulfuric acid (374 mg, equal to 2.2 mmol H+) and NaI (2.2 mmol) were added. The mixture was stirred magnetically at room temperature and the progress of the reaction was monitored by TLC or GC until the starting sulfoxide was completely consumed. The reaction mixture was then neutralized using NaOH solution (0.5 M, 1 ml), and subsequently the enough well-powdered Na2S2O3 · 5H2O was added to mixture with stirring to react with iodine. The mixture was then extracted with EtOAc (5 × 1 ml). The organic layers were decanted, combined, dried over Na2SO4, filtered and concentrated. The crude product was further purified by silica gel chromatography using n-hexane as eluent to provide the desired product in excellent yields.
89% With indium powder; molybdenum pentachloride In tetrahydrofuran at 20℃; for 0.0833333h;
89% With indium powder; tungsten hexachloride In tetrahydrofuran at 20℃; for 0.0833333h;
89% With iodine; tiolacetic acid In acetonitrile at 20℃; for 4.16667h;
89% Stage #1: di(p-tolyl) sulfoxide With oxalyl dichloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
87% With carbon dioxide; water monomer; iron(0) at 80℃; for 10h; Autoclave; Green chemistry; chemoselective reaction;
86% With chloro-trimethyl-silane; ethylene; sodium bromide In acetonitrile for 0.5h; Ambient temperature;
85% With cobalt(III) chloride In diethyl ether at 0℃; for 1h;
84% With sodium tetrahydridoborate; iron(III) chloride In ethanol; water monomer 1.) room temperature, 2 h, 2.) reflux, 5 - 10 min;
84% With tris[N,N-bis(trimethylsilyl)amide]yttrium; phenylsilane at 120℃; for 24h; Inert atmosphere; 2 Example 2 The preparation of 4,4'-tolyl sulfide, the structural formula is as follows: Under nitrogen protection, the raw materials 4,4'-tolyl sulfoxide (0.3 mmol) and phenylsilane (0.9 mmol) were added, and the catalyst Y[N(SiMe3)2]3 (0.03 mmol) was added, and the reaction was carried out at 120 °C for 24 h. The product isolation yield was 84%.
77% With bis(η5-cyclopentadienyl) titanium dichloride; samarium In tetrahydrofuran for 1h; Ambient temperature;
75% Stage #1: di(p-tolyl) sulfoxide With oxalyl dichloride In dichloromethane at -78℃; for 0.583333h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane for 0.166667h; Inert atmosphere; 7 In 25 ml of the reaction tube for vacuum, nitrogen three times, placed at -78 ,4,4-dimethyldiphenylsulfoxide (116 mg, 1.0 eq) and re-distilled dichloromethane DCM (3 mL, 0.17 M) were added under nitrogen atmosphere,Then oxalyl chloride (63 μL, 1.5 eq.) Was added. After 35 minutes of reaction, triethylamine Et3N (101.3 mg, 2.0 eq.) Was added.After 10 minutes, the reaction process was tracked by thin layer chromatography,The developing agent was a petroleum ether / ethyl acetate volume ratio of 40/1, the reaction was monitored,The reaction mass was concentrated by vacuum and separated by column chromatography to give a white solid in 75% yield.
72% With benzylic alcohol at 135℃; for 20h; Inert atmosphere; Schlenk technique; chemoselective reaction;
66% With triethylsilane; tris(pentafluorophenyl)borate In neat (no solvent) at 100℃; for 8h; Glovebox; Inert atmosphere; Reduction of Sulfoxides and Sulfones; General Procedure General procedure: In a glovebox, an oven-dried 1-mL screw-capped sealed tube with a magnetic stir bar was charged with B(C6F5)3 (10 mol%), Et3SiH (10 equiv), and the indicated oxidized sulfur compound (0.20 mmol). The tube was sealed properly and transferred to an oil bath preheated at100 °C. After 8 h, the reaction was cooled to r.t. and passed through asmall plug of silica gel using Et2O. The crude material was collected ina glass vial and subjected to GLC analysis to determine the conversion with respect to starting material. The ethereal solution was dried (Na2SO4) and filtered, and the solvent was removed under reduced pressure. The mixture was then subjected to high vacuum at 70 °C until the unreacted hydrosilane was removed from the system. If needed, the residue was purified further by flash column chromatography (silica gel, cyclohexane/Et2O 9:1) to afford the desired sulfides.
60% With chloro-trimethyl-silane; 3-mercaptopropionic acid In acetonitrile at 20℃; for 48h;
54% With ethynylmagnesium bromide; di-i-propyl amine In diethyl ether Heating;
41% Stage #1: di(p-tolyl) sulfoxide With diiron nonacarbonyl In toluene at 100℃; for 24h; Stage #2: With boron trifluoride diethyl ether complex In toluene at 100℃; for 1h; Procedure for the Deoxygenation of Sulfoxide withPoly(methylhydrosiloxane) 1 Aflask was charged with Fe2(CO)9 (0.54 mmol,10.0 mol %), p-tolyl sulfoxide 6 (5.6 mmol) and PMHS(1.0 g, 16.7 mmol). After addition of toluene (20 mL) thereaction mixture was stirred in a preheated oil bath at100 C for 24 h. The toluene was removed in vacuum. To the flask a Vigreux columnand a distillation head were connected. The flask washeated to 100 C (oil bath temperature) and boron trifluoridediethyl etherate 2 (1.0 equiv. based on the polymersubunit, 2.4 g) was added. The mixture was stirred andheated for 60 min. The formed low-boiling compoundswere continuously distilled off and collected at low temperature(-196 C). After one hour the yield was determinedand the mixture was analyzed by NMR. The residue in the reaction flask was treated withaqueous sodium hydroxide solution and ethyl acetate(50 mL) was added. The aqueous layer was extracted withethyl acetate (2 9 50 mL). The organic layer was washedwith water, brine and dried over Na2SO4. After removal ofthe solvent the residue was dissolved in ethyl acetate andfiltered through a short plug of silica. Afterwards the solventwas removed and the solid residue was analyzed byNMR and GC-MS. A mixture of sulfoxide 6 and sulfide 7was detected and the yield of the sulfide was calculated byNMR.
90 % Chromat. With hexafluoroantimonic acid In liquid sulphur dioxide at -5℃;
With zinc powder In glacial acetic acid
60 % Spectr. With sodium tetrahydridoborate; cobalt(II) chloride In ethanol for 48h; Ambient temperature; reagents ratio dependence;
95 % Spectr. With bis(cyclopentadienyl) iron(II); trifluoroacetic anhydride In chloroform at 20℃; for 24h;
With glacial acetic acid; zinc powder
> 99 %Chromat. With copper(II) bis(2,4-pentanedionate); diphenylsilane In toluene at 100℃; for 12h;
> 98 %Chromat. With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 80℃; for 4h; Inert atmosphere; 4.4. Reduction of aryl sulfoxides General procedure: To a magnetically stirred solution of aryl sulfoxide (0.18 M; 50 mg, ca. 2.5 mmol) in toluene (ca. 1.5 mL) kept under inert atmosphere, tris(trimethylsilyl)silane (2 equiv) and AIBN (0.2 equiv) were consecutively added and the reaction mixture was warmed up at 80 °C. The reaction was monitored by gas chromatography, after calibration of the equipment using the reference compounds. The consumption of the starting material was evidenced by GC together with the formation of the sulfide product, and quantitatively evaluated by the calibration curves of commercially available compounds.
93 %Chromat. With hydrogen In decane at 100℃; for 2h; Schlenk technique; Sealed tube;
60 mg With methanol; sodium tertiary butoxide In 1,4-dioxane at 120℃; for 24h;
With hydrogen In toluene at 20℃; Irradiation; Green chemistry;
100 %Chromat. With hydrogen In methanol at 50℃; for 15h; Autoclave;
98 %Chromat. With hydrogen In toluene at 160℃; for 12h; Autoclave; Molecular sieve;

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  • 12
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 599-66-6 ]
YieldReaction ConditionsOperation in experiment
83%; 12% With [ReOCl3(PPh3)2]; In chloroform; for 17h;Reflux; General procedure: To a solution of ReOCl3(PPh3)2 (10.0 mol %) in CHCl3 (3 mL) was added the sulfoxide (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Table 1, Table 2 and Table 3) and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford sulfides and sulfones, which are all known compounds.
  • 13
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 95-57-8 ]
  • [ 106-48-9 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride; phenol In dichloromethane at 0 - 25℃;
  • 14
  • [ 136378-30-8 ]
  • [ 67501-10-4 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
1: 33% 2: 19% With tert.-butyl lithium In tetrahydrofuran at -95℃;
  • 15
  • [ 16491-20-6 ]
  • [ 945-51-7 ]
  • [ 67501-10-4 ]
  • [ 77096-69-6 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
1: 38% 2: 15% 3: 24% With tert.-butyl lithium In tetrahydrofuran at -80℃; for 15h; Further byproducts given;
  • 16
  • [ 16491-20-6 ]
  • [ 945-51-7 ]
  • [ 77096-69-6 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
1: 24% 2: 22% 3: 48% With phenyllithium In tetrahydrofuran at -85℃; for 0.25h;
1: 42% 2: 16% 3: 31% With phenylmagnesium bromide In tetrahydrofuran for 0.25h; Heating;
  • 17
  • [ 455-16-3 ]
  • [ 108-88-3 ]
  • [ 599-66-6 ]
  • [ 1774-35-2 ]
  • 18
  • [ 1774-35-2 ]
  • [ 791-28-6 ]
  • [ 945-51-7 ]
  • [ 77096-69-6 ]
  • [ 18957-70-5 ]
  • [ 6840-28-4 ]
YieldReaction ConditionsOperation in experiment
1: 28% 2: 19% 3: 11% 4: 10% With tert.-butyl lithium In tetrahydrofuran at -95℃; for 0.25h;
  • 19
  • [ 1774-35-2 ]
  • KMnO4 [ No CAS ]
  • [ 599-66-6 ]
  • 20
  • [ 1774-35-2 ]
  • C14H14F2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With pyridine; hydrogen fluoride; (bis-(2-methoxyethyl)amino)sulfur trufluoride In benzene for 3.5h;
  • 21
  • [ 108-88-3 ]
  • [ 10381-68-7 ]
  • [ 1774-35-2 ]
  • [ 5097-05-2 ]
YieldReaction ConditionsOperation in experiment
1: 79 % Chromat. 2: 13 % Chromat. 3: 2 % Chromat. With 1-(n-butyl)-3-methylimidazolium tetrachloroaluminate; thionyl chloride at 20℃; for 0.0833333h;
1: 55 %Chromat. 2: 34 %Chromat. 3: 11 %Chromat. With aluminum (III) chloride; thionyl chloride at 25℃; Approach 2 General procedure: The reactions were conducted in the fume hood at 25 °C, with the molar ratio of PhX:SOCl2:AlCl3 being 2:1:1 and usage of SOCl2 approximately 10 mmol. For each reaction, SOCl2 was added dropwise to the PhX-AlCl3 mixture (X=CH3 or Cl) with constantstirring. The reaction took place quickly, indicated by bubbling asabove. After all the SOCl2 was added, the reaction went to completion, indicated by cessation of bubbling. Then aqueous work-up wasperformed as above. The final product was characterised by GC-MS, and the results are shown in Table 1.
  • 22
  • [ 108-86-1 ]
  • [ 1774-35-2 ]
  • bis(4-methylphenyl)phenylsulfonium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: bromobenzene With magnesium In tetrahydrofuran Stage #2: di(p-tolyl) sulfoxide With chloro-trimethyl-silane In tetrahydrofuran at 25℃;
  • 23
  • [ 911820-09-2 ]
  • [ 624-31-7 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
81% With potassium hydroxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water; toluene at 70℃; for 2h;
  • 24
  • [ 1774-35-2 ]
  • [ 22417-22-7 ]
YieldReaction ConditionsOperation in experiment
S.4 Synthesis of tris(4-methylphenyl)sulfonium chloride Synthesis Example 4 Synthesis of tris(4-methylphenyl)sulfonium chloride The target compound was obtained by following the procedure of Synthesis Example 1 aside from using bis(4-methylphenyl)sulfoxide instead of the diphenyl sulfoxide and 4-chlorotoluene instead of the chlorobenzene in Synthesis Example 1, and increasing the amount of water for extraction.
S.4 Synthesis of tris(4-methylphenyl)sulfonium chloride Synthesis Example 4 Synthesis of tris(4-methylphenyl)sulfonium chloride The target compound was obtained by following the procedure of Synthesis Example 1 aside from using bis(4-methylphenyl) sulfoxide instead of the diphenyl sulfoxide and 4-chlorotoluene instead of the chlorobenzene in Synthesis Example 1, and increasing the amount of water for extraction.
S.1.4 Synthesis of tris(4-methylphenyl)sulfonium Chloride Synthesis Example 1-4 Synthesis of tris(4-methylphenyl)sulfonium Chloride The target compound was obtained by following the procedure of Synthesis Example 1-1 aside from using bis(4-methylphenyl)sulfoxide instead of the diphenyl sulfoxide and 4-chlorotoluene instead of the chlorobenzene in Synthesis Example 1-1, and increasing the amount of water for extraction.
S.1.4 Synthesis of tris(4-methylphenyl)sulfonium chloride Synthesis Example 1-4 Synthesis of tris(4-methylphenyl)sulfonium chloride The target compound was obtained by following the procedure of Synthesis Example 1-1 aside from using bis(4-methylphenyl) sulfoxide instead of the diphenyl sulfoxide and 4-chlorotoluene instead of the chlorobenzene in Synthesis Example 1-1, and increasing the amount of water for extraction.
S.1.4 Synthesis of tris(4-methylphenyl)sulfonium chloride Synthesis Example 1-4 Synthesis of tris(4-methylphenyl)sulfonium chloride The target compound was obtained by following the procedure of Synthesis Example 1-1 aside from using bis(4-methylphenyl)sulfoxide instead of the diphenyl sulfoxide and 4-chlorotoluene instead of the chlorobenzene in Synthesis Example 1-1, and increasing the amount of water for extraction.

  • 25
  • [ 1774-35-2 ]
  • [ 100-66-3 ]
  • C21H21OS(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: di(p-tolyl) sulfoxide; methoxybenzene With Methanesulfonic anhydride at 20℃; for 3h; Stage #2: With potassium hexafluorophosphate In water Synthesis of TAS-13 Added to a one liter flask provided with a calcium chloride tube and a thermometer, were 32 g of phosphorus oxide and 288 g of methanesulfonic acid, stirred and heated for three hours at a temperature of 80° C.-90° C. After allowed to cool to room temperature, 69.1 g of p-toluylsulfoxide and 33 g of anisole were added and stirred for three hours at room temperature. Added to a five liter conical beaker, was 55.2 g of potassium hexafluorophosphate and dissolved into three liter of purified water, and the above reacted solution was added bit by bit while mechanically stirred to obtain a nougat-like amorphous substance. After stirring, the supernatant liquid was decanted. Added to the soft candy-like residue, was 600 ml of methylene chloride, and later a solution of 25 g of hexafluorophosphoric acid in 500 ml of purified water was added and dispersed for one hour. After siphoning off the water layer, activated carbon was added to decolor the methylene chloride layer, after which activated carbon was filtered off, and vacuum concentrated to obtain the crude product, which was refined using an activated alumina column treatment, and then the solvent was vacuum concentrated to obtain 132.6 g of raw crystals. To the crystals, 300 ml of isopropyl alcohol and 10-30 ml of methylene chloride were added, heated and dispersed in a water bath of 60-70° C., and after standing to cool to approximately room temperature, further added was 200 ml of isopropyl alcohol. After stirring for one hour under room temperature, crystals were filtered out to obtain TAS-13, the yield being 123.7 g at a yield of 88%. The crystals were confirmed to be the specified substance using a 1H-NMR and a mass spectrometry
  • 26
  • [ 6407-30-3 ]
  • [ 1774-35-2 ]
  • 2-(8-benzoyl-dibenzothiophenyl)-di-p-tolylsulfonium hexafluoro-antimonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: dibenzo[b,d]thiophen-2-yl(phenyl)methanone; di(p-tolyl) sulfoxide With sulfuric acid In water at 20℃; for 10h; Stage #2: With potassium hexafluoroantimonate In methanol; dichloromethane; water; toluene for 2h; 1 [Synthesis example-(1)]Synthesis of 2-(8-benzoyl-dibenzothiophenyl)-di-p-tolylsulfonium hexafluoro-antimonate. (Compound 1.) 82.0g of benzoyl chloride was added into the mixture of aluminium chloride (93.3g), dibenzothiophene(107.5g) and 1,2-dichloroethane(650g)using 500mL three necked flask, then reaction was carried out for 2hrs at 25°C. The reaction mixture was poured into 1000g of ice water in a beaker (5000mL). The 1,2-dichloroethane layer was washed by 1000g of water three times. After condensing the 1,2-dichloroethane layer under reduced pressure, 160.4g of 8-benzoyl-dibenzothiophene was obtained (yield 95%). 46.0g of di-p-tolyl sulfoxide were added into 295g of 95% sulfuric acid with stirring using 500mL three necked flask. As soon as adding, the reaction mixture was colored to dark brown. And, 57.6g of 8-benzoyl-dibenzothiophene obtained above, was added in it. Stirring was continued for 10hrs at room temperature. Then, the reaction mixture and 300g of toluene were poured into 500g of methanol and 500g of ice in 3000mL beaker. The underlayer was separated out, and after it was extracted with 500g of methylene chloride, 1000g of water was added therein and stirred, and 36.8g of KSbF6 was added, and stirring was continued for two hours. After the methylene chloride layer was washed with 1000g of water twice. 90.53g of a product was obtained as white powder (yield 70%) by condensing under reduced pressure. This product was identified as 2-(8-benzoyl-dibenzothiophenyl)-di-p-tolylsulfonium hexafluoro-antimonate.
  • 27
  • [ 1774-35-2 ]
  • [ 882867-59-6 ]
YieldReaction ConditionsOperation in experiment
78.1% With N-Bromosuccinimide In tetrachloromethane at 20℃; for 12h; Heating / reflux; A mixture of 4-methyl-1-[(4-methylphenyl)sulfinyl]benzene (1.15 g, 5.00 mmol), N-bromosuccinimide (1.08 g, 6.00 mmol), 2,2'-azobis-(2-methylpropionitrile) (100 mg, 0.600 mmol), and CCl4 (25.0 mL) as solvent was stirred for 5 min at room temperature and then heated to reflux for 12 h. The reaction mixture was cooled to room temperature and filtered and the solvent was removed in vacuo, affording a crude product which was used in the next step without any further purification (1.21 g, 78.1% yield). 1H NMR (CDCl3) δ 7.71-7.57 (m, 2H), 7.57-7.40 (m, 4H), 7.36-7.16 (m, 2H), 4.46 (s, 2H), 2.37 (s, 3H).
78.1% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 25℃; for 12h; Heating / reflux; A mixture of 4-methyl-1-[(4-methylphenyl)sulfinyl]benzene (1.15 g, 5.00 mmol), N-bromosuccinimide (1.08 g, 6.00 mmol), 2,2'-azobis-(2-methylpropionitrile) (100 mg, 0.600 mmol), and CCl4 (25.0 mL) as solvent was stirred for 5 min at room temperature and then heated to reflux for 12 h. The reaction mixture was cooled to room temperature and filtered and the solvent was removed in vacuo, affording a crude product which was used in the next step without any further purification (1.21 g, 78.1%). 1H NMR (CDCl3) 6 7.71-7.57 (m, 2H), 7.57-7.40 (m, 4H), 7.36-7.16 (m, 2H), 4.46 (s, 2H), 2.37 (s, 3H).
  • 28
  • [ 881041-55-0 ]
  • [ 1774-35-2 ]
  • [ 1097213-61-0 ]
  • C27H28NS(1+)*ClO4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% Stage #1: N-mesitylpyrrole; di(p-tolyl) sulfoxide With trifluoroacetic anhydride In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: With lithium perchlorate In dichloromethane at 20℃; Inert atmosphere;
  • 29
  • [ 881041-55-0 ]
  • [ 1774-35-2 ]
  • [ 1097213-62-1 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: N-mesitylpyrrole; di(p-tolyl) sulfoxide With trifluoroacetic anhydride In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: With lithium perchlorate In dichloromethane at 20℃; Inert atmosphere; Stage #3: With sodium tetraphenyl borate In methanol at 20℃; for 0.5h; Inert atmosphere;
  • 30
  • [ 10381-71-2 ]
  • [ 624-31-7 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
47% With tris-(dibenzylideneacetone)dipalladium(0); potassium <i>tert</i>-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene for 2h; Reflux;
  • 31
  • [ 6407-30-3 ]
  • [ 1774-35-2 ]
  • [ 60805-12-1 ]
  • [ 1224640-79-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: dibenzo[b,d]thiophen-2-yl(phenyl)methanone; di(p-tolyl) sulfoxide With sulfuric acid; acetic anhydride; acetic acid In dichloromethane at 10 - 50℃; for 25.25h; Inert atmosphere; Stage #2: tris-(trifluoromethanesulfonyl)methane acid In dichloromethane; water at 20℃; Cooling with ice; 1 5 g (17.3 mmol) of 2-benzoyldibenzothiophene, 3.98 g (17.3 mmol) of p-tolylsulfoxide, 17.5 ml of acetic anhydride, 17.5 ml of acetic acid and 4.3 ml of CH2Cb are mixed in 200 ml three-necked flask under a nitrogen atomosphere and cooled by ice bath. To the suspension, 6.5 ml of sulfuric acid is added dropwise during 15 min with keeping the temperature below 10 0C. The reaction mixture is stirred at room temperature for 18 hours, followed by at 50 0C for 7 hours. After the reaction mixture is cooled by ice bath, 8.5 g (20.8 mmol) of 58.5 % aqueous solution of tris(trifluoromethanesulfonyl)methane is added with cooled. The reaction mixture is stirred at room temperature overnight, poured into water, and extracted with CH2CI2. The organic phase is washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography using tert-butylmethylether/ethyl acetate (3:1 ) as eluent, yielding the title compound of example 1 as a pale yellow sold with melting point of 55 0C.The structure is confirmed by the 1H-NMR spectrum (CDCI3). δ [ppm]: 2.50 (s, 6H), 7.47-7.60 (m, 10H), 7.60-7.70 (m, 2H), 7.83 (d, 2H), 7.97-8.06 (m, 2H), 8.24 (d, 1 H), 8.35 (s, 1 H), 8.57 (s, 1 H); 19F-NMR (CDCI3) δ -76.84 (s, 9F).
  • 32
  • [ 1774-35-2 ]
  • [ 492-97-7 ]
  • bis(4-methylphenyl)-5-(2,2'-bithienyl)sulfonium hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: di(p-tolyl) sulfoxide; 2,2'-Bithiophene With methanesulfonic acid; acetic anhydride at 0 - 30℃; for 5h; Stage #2: With potassium hexafluorophosphate In water; chlorobenzene at 30 - 50℃; for 1h; A1; B1; C1 In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 3.5 g (0.015 mol) of bis(4-methylphenyl) sulfoxide, 2.5 g (0.015 mol) of 2,2'-bithiophene and 7.7 g (0.075 mol) of acetic anhydride were charged and 5.8 g (0.06 mol) of methanesulfonic acid was added dropwise over 1 hour while maintaining the inner temperature at 0 to 10°C,. After completion of the dropwise addition, stirring was conducted at the same temperature for 2 hours and also stirring was conducted at 20 to 30°C for 2 hours to obtain a reaction solution of a condensation reaction product. In a 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 2.8 g (0.015 mol) of potassium hexafluorophosphate, 40 g of water and 30 g of monochlorobenzene were charged and the entire amount of the reaction solution was added dropwise over 30 minutes while maintaining the inner temperature at 30 to 50°C. After stirring at 40 to 50°C for 30 minutes, the monochlorobenzene layer was separated and monochlorobenzene was distilled off to obtain 7.5 g of a green concentrate. This concentrate was purified by silica gel column chromatography to obtain 5.4 g of bis(4-methylphenyl)-5-(2,2'-bithienyl)sulfonium hexafluorophosphate, which is the aromatic sulfonium salt described in Patent Document 3, as a pale yellow solid. As a result of the measurement by high performance liquid chromatograph, purity of the resultant bis(4-methylphenyl)-5-(2,2'-bithienyl)sulfonium hexafluorophosphate was 98.9%. A molar extinction coefficient was determined by measuring using a spectrophotometer for ultraviolet and visible region (manufactured by Shimadzu Corporation under the trade name of UV-2500(PC)S). Molar extinction coefficient (365 nm); 1.2 × 104
  • 33
  • [ 3988-99-6 ]
  • [ 1774-35-2 ]
  • (thiodi-5,2-thienylene)bis[bis(4-methylphenyl)sulfonium] bishexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: bis(thien-2-yl)sulfide; di(p-tolyl) sulfoxide With methanesulfonic acid; acetic anhydride at 0 - 10℃; for 3h; Stage #2: With potassium hexafluorophosphate In water; chlorobenzene at 30 - 50℃; for 1h; A4 In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 4.6 g (0.02 mol) of bis(4-methylphenyl) sulfoxide, 2.0 g (0.01 mol) of 2,2'-dithienyl sulfide and 10.2 g (0.1 mol) of acetic anhydride were charged and 7.7 g (0.08 mol) of methanesulfonic acid was added dropwise over 1 hour while maintaining the inner temperature at 0 to 10°C. After completion of the dropwise addition, stirring was conducted for 2 hours while maintaining at the same temperature to obtain a reaction solution as a condensation reaction product. In a 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 3.7 g (0.02 mol) of potassium hexafluorophosphate, 40 g of water and 30 g of monochlorobenzene were charged and the entire amount of the reaction solution was added dropwise over 30 minutes while maintaining the inner temperature at 30 to 50°C. After stirring at 40 to 50°C for 30 minutes, the monochlorobenzene layer was separated and monochlorobenzene was distilled off to obtain 8.5 g of a brown concentrate. This concentrate was purified by silica gel column chromatography to obtain 6.4 g (0.007 mol) of (thiodi-5,2-thienylene)bis[bis(4-methylphenyl)sulfonium] bishexafluorophosphate as a pale yellow solid. As a result of the measurement by high performance liquid chromatograph, purity of the resultant (thiodi-5,2-thienylene)bis[bis(4-methylphenyl)sulfonium] bishexafluorophosphate was 98.3%. Also, the yield to 2,2'-dithienyl sulfide was 70%. It was confirmed by analytical results shown below that the resultant pale yellow solid is (thiodi-5,2-thienylene)bis[bis(4-methylphenyl)sulfonium] bishexafluorophosphate in which all R1a, R2a, R3a and R4a in the formula (A1) are 4-methylphenyl groups and X- is a hexafluorophosphoric acid ion. The molar extinction coefficient was determined by measuring using a spectrophotometer for ultraviolet and visible region (manufactured by Shimadzu Corporation under the trade name of UV-2500(PC)S). Elemental analysis: C; 47.1%, H; 3.4%, F; 25.1%, S; 17.6% (theoretical value: C; 47.26%, H; 3.53%, F; 24.92%, S; 17.52%) 1H-Nuclear magnetic resonance spectrum (400 MHz, CD2Cl2) δ (ppm): 2.50(s, 12H), 7.46-7.48(m, 2H), 7.52-7.56(m, 8H), 7.57-7.62(m, 8H), 7.69(d, 2H) Molar extinction coefficient (365 nm); 1.5 × 103
  • 34
  • [ 1774-35-2 ]
  • [ 1655-07-8 ]
  • [ 1308853-72-6 ]
YieldReaction ConditionsOperation in experiment
59% With trifluoroacetic anhydride In acetonitrile at 25℃; for 24h; Inert atmosphere;
59% With trifluoroacetic anhydride In acetonitrile at 0℃; for 24h; Inert atmosphere;
  • 35
  • [ 1774-35-2 ]
  • [ 3536-97-8 ]
  • 1-(isopropylsulfinyl)-4-methylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: diisopropylmagnesium With n-butyllithium; endo-borneol In tetrahydrofuran; diethyl ether; hexane at 22℃; for 0.166667h; Inert atmosphere; Stage #2: di(p-tolyl) sulfoxide In tetrahydrofuran; diethyl ether; hexane at -40℃; for 0.333333h; Inert atmosphere;
  • 36
  • [ 1774-35-2 ]
  • [ 873-76-7 ]
  • [ 620-94-0 ]
  • [ 104-88-1 ]
YieldReaction ConditionsOperation in experiment
1: 70% 2: 99% With per-rhenic acid In toluene for 17h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 37
  • [ 873-75-6 ]
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 1122-91-4 ]
YieldReaction ConditionsOperation in experiment
1: 98% 2: 99% With per-rhenic acid In toluene for 17h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 38
  • [ 459-56-3 ]
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 459-57-4 ]
YieldReaction ConditionsOperation in experiment
1: 97% 2: 90% With per-rhenic acid In toluene for 17h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 39
  • [ 18282-51-4 ]
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 15164-44-0 ]
YieldReaction ConditionsOperation in experiment
1: 99% 2: 88% With per-rhenic acid In toluene for 17h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 40
  • [ 1774-35-2 ]
  • [ 100-51-6 ]
  • [ 620-94-0 ]
  • [ 100-52-7 ]
YieldReaction ConditionsOperation in experiment
1: 95% 2: 83% With per-rhenic acid In toluene for 17h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 41
  • [ 33091-15-5 ]
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 1144-74-7 ]
YieldReaction ConditionsOperation in experiment
1: 85% 2: 55% With per-rhenic acid In toluene for 24h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 42
  • [ 90-97-1 ]
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 90-98-2 ]
YieldReaction ConditionsOperation in experiment
1: 60% 2: 35% With per-rhenic acid In toluene for 24h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 43
  • [ 619-73-8 ]
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 555-16-8 ]
YieldReaction ConditionsOperation in experiment
1: 99% 2: 96% With per-rhenic acid In toluene for 17h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 44
  • [ 1774-35-2 ]
  • [ 6908-41-4 ]
  • [ 620-94-0 ]
  • [ 1571-08-0 ]
YieldReaction ConditionsOperation in experiment
1: 85% 2: 97% With per-rhenic acid In toluene for 24h; Reflux; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 45
  • [ 104-54-1 ]
  • [ 1774-35-2 ]
  • [ 620-94-0 ]
  • [ 104-55-2 ]
YieldReaction ConditionsOperation in experiment
1: 68% 2: 80% With per-rhenic acid In toluene for 24h; Reflux; chemoselective reaction; General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.
  • 46
  • [ 1774-35-2 ]
  • [ 31179-52-9 ]
  • [ 53040-92-9 ]
YieldReaction ConditionsOperation in experiment
50% With C30H21F6N2NiO2P In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Inert atmosphere;
  • 47
  • [ 106-38-7 ]
  • [ 934-72-5 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
85% With (chloro)phenylallyl[1,3‐bis(2,6‐bis(diphenylmethyl)‐4‐methylphenyl)imidazo‐2‐ylidene]palladium(II); potassium 2-methylbutan-2-olate In 1,4-dioxane at 110℃; for 20h;
  • 48
  • [ 106-43-4 ]
  • [ 934-72-5 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
71% With (chloro)phenylallyl[1,3‐bis(2,6‐bis(diphenylmethyl)‐4‐methylphenyl)imidazo‐2‐ylidene]palladium(II); potassium 2-methylbutan-2-olate In 1,4-dioxane at 110℃; for 20h;
  • 49
  • [ 108-88-3 ]
  • [ 620-94-0 ]
  • [ 10381-68-7 ]
  • [ 1774-35-2 ]
  • [ 5097-05-2 ]
YieldReaction ConditionsOperation in experiment
1: 58 %Chromat. 2: 27 %Chromat. 3: 8 %Chromat. 4: 7 %Chromat. With aluminum (III) chloride; thionyl chloride at 70℃; Approach 1 General procedure: The reactions were conducted in the fume hood at 25 °Cand 70 °C, respectively, with the molar ratio of PhX:SOCl2:AlCl3 being 2:1:1 and usage of SOCl2 approximately 10 mmol. For eachreaction, granular AlCl3 was added piecewise to the PhX-SOCl2 mixture (X=CH3 or Cl) in a large test tube (~ 80 mL) as follows: First, one piece of AlCl3 was added and gas (HCl) bubbles started to form immediately. The piece of AlCl3 was crushed using a stirring rod. When most of the piece of AlCl3 had dissolved and bubbling occurredvery slowly, another piece of AlCl3 was added. All the AlCl3 granules were eventually added into the PhX-SOCl2 mixture piece-by-piece. The solution was initially light green and it turned dark green as the reaction went to completion, indicated by ceasing of bubbling after all the AlCl3 had been added. Then iced water (40 mL) was poured into thereaction mixture and the green colour disappeared. This was followed by addition of diethyl ether (20 mL). All the contents were transferredinto a separating funnel and shaken well to assure the organic productbeing fully extracted into the ether phase. The ether and water phaseswere separated. The water phase was extracted by diethyl ether (20 mL) again. Then all the ether solutions were combined and dried by anhydrous sodium sulfate. The dried ether solution was filtered off and left in the fume hood. Eventually, all the diethyl ether solvent evaporated, giving the final reaction product. The product was thencharacterised by GC-MS, and the results are shown in Table 1.
  • 50
  • [ 108-88-3 ]
  • [ 599-66-6 ]
  • [ 10381-68-7 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
16%Chromat.; 26%Chromat.; 50%Chromat. With aluminum (III) chloride; thionyl chloride; at 25℃; General procedure: The reactions were conducted in the fume hood at 25 Cand 70 C, respectively, with the molar ratio of PhX:SOCl2:AlCl3 being 2:1:1 and usage of SOCl2 approximately 10 mmol. For eachreaction, granular AlCl3 was added piecewise to the PhX-SOCl2 mixture (X=CH3 or Cl) in a large test tube (~ 80 mL) as follows: First, one piece of AlCl3 was added and gas (HCl) bubbles started to form immediately. The piece of AlCl3 was crushed using a stirring rod. When most of the piece of AlCl3 had dissolved and bubbling occurredvery slowly, another piece of AlCl3 was added. All the AlCl3 granules were eventually added into the PhX-SOCl2 mixture piece-by-piece. The solution was initially light green and it turned dark green as the reaction went to completion, indicated by ceasing of bubbling after all the AlCl3 had been added. Then iced water (40 mL) was poured into thereaction mixture and the green colour disappeared. This was followed by addition of diethyl ether (20 mL). All the contents were transferredinto a separating funnel and shaken well to assure the organic productbeing fully extracted into the ether phase. The ether and water phaseswere separated. The water phase was extracted by diethyl ether (20 mL) again. Then all the ether solutions were combined and dried by anhydrous sodium sulfate. The dried ether solution was filtered off and left in the fume hood. Eventually, all the diethyl ether solvent evaporated, giving the final reaction product. The product was thencharacterised by GC-MS, and the results are shown in Table 1.
  • 51
  • [ 108-88-3 ]
  • [ 620-94-0 ]
  • [ 10381-68-7 ]
  • [ 1774-35-2 ]
  • [ 2943-42-2 ]
YieldReaction ConditionsOperation in experiment
1: 35 %Chromat. 2: 30 %Chromat. 3: 20 %Chromat. 4: 10 %Chromat. With aluminum (III) chloride; thionyl chloride at -10℃; for 1h; p-CH3C6H4SO2S(p-C6H4CH3) The yield enhancement was conducted by the AlCl3-catalysed reaction of toluene (PhCH3) and SOCl2 in the fumehood at -10 °C, with the molar ratio of PhCH3:SOCl2:AlCl3 being 1:1:1 and usage of SOCl2 approximately 25 mmol. With constantstirring PhCH3 was added dropwise to a SOCl2-AlCl3 mixture.The procedure and observations were the same as those of the abovebenzene reactions. The GC-MS analysis showed that the productcontained several components whose identities and molar percentages (normalised) are indicated in Eqn (5).
  • 52
  • [ 108-88-3 ]
  • [ 71-43-2 ]
  • [ 945-51-7 ]
  • [ 10381-68-7 ]
  • [ 77096-69-6 ]
  • [ 1774-35-2 ]
  • [ 50986-89-5 ]
YieldReaction ConditionsOperation in experiment
1: 33 %Chromat. 2: 32 %Chromat. 3: 16 %Chromat. 4: 10 %Chromat. 5: 6 %Chromat. With aluminum (III) chloride; thionyl chloride at 25℃; Approach 1 General procedure: The reactions were conducted in the fume hood at 25 °Cand 70 °C, respectively, with the molar ratio of PhX:SOCl2:AlCl3 being 2:1:1 and usage of SOCl2 approximately 10 mmol. For eachreaction, granular AlCl3 was added piecewise to the PhX-SOCl2 mixture (X=CH3 or Cl) in a large test tube (~ 80 mL) as follows: First, one piece of AlCl3 was added and gas (HCl) bubbles started to form immediately. The piece of AlCl3 was crushed using a stirring rod. When most of the piece of AlCl3 had dissolved and bubbling occurredvery slowly, another piece of AlCl3 was added. All the AlCl3 granules were eventually added into the PhX-SOCl2 mixture piece-by-piece. The solution was initially light green and it turned dark green as the reaction went to completion, indicated by ceasing of bubbling after all the AlCl3 had been added. Then iced water (40 mL) was poured into thereaction mixture and the green colour disappeared. This was followed by addition of diethyl ether (20 mL). All the contents were transferredinto a separating funnel and shaken well to assure the organic productbeing fully extracted into the ether phase. The ether and water phaseswere separated. The water phase was extracted by diethyl ether (20 mL) again. Then all the ether solutions were combined and dried by anhydrous sodium sulfate. The dried ether solution was filtered off and left in the fume hood. Eventually, all the diethyl ether solvent evaporated, giving the final reaction product. The product was thencharacterised by GC-MS, and the results are shown in Table 1.
  • 53
  • [ 4419-57-2 ]
  • [ 1774-35-2 ]
  • 2-(5-methyl-2-(p-tolylthio)phenyl)-1-(pyrrolidin-1-yl)pentan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 1-(pyrrolidin-1-yl)pentan-1-one With 2-iodopyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: di(p-tolyl) sulfoxide In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; chemoselective reaction;
  • 54
  • [ 1774-35-2 ]
  • iminodi-p-tolyl-λ6-sulfanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With 1,10-Phenanthroline; O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) sulfate In acetonitrile at 30℃; for 48h; Inert atmosphere; Sealed tube;
84% With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]; O-(2,4-dinitrophenyl)hydroxylamine In 2,2,2-trifluoroethanol at 0 - 20℃; for 22h; Inert atmosphere;
76% With [bis(acetoxy)iodo]benzene; ammonium acetate In methanol at 20℃; for 12h;
With sodium azide; sulfuric acid In chloroform at 0 - 45℃; Reflux;
With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 20℃; for 0.5h;
With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 25℃; for 0.5h;

  • 55
  • [ 1774-35-2 ]
  • [ 1622424-35-4 ]
  • [ 1622424-57-0 ]
YieldReaction ConditionsOperation in experiment
90% With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 1h; Inert atmosphere;
  • 56
  • [ 1774-35-2 ]
  • [ 184824-37-1 ]
YieldReaction ConditionsOperation in experiment
61% With iodobenzene; silver(I) acetate; acetic acid; palladium dichloride In 1,1,2,2-tetrachloroethane at 120℃; for 48h; Sealed tube;
  • 57
  • [ 108-86-1 ]
  • [ 201230-82-2 ]
  • [ 1774-35-2 ]
  • [ 4403-69-4 ]
  • [ 25855-20-3 ]
  • [ 620-94-0 ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; catacxium A In N,N-dimethyl-formamide at 140℃; for 36h; Inert atmosphere; Autoclave;
  • 58
  • [ 1774-35-2 ]
  • [ 557-18-6 ]
  • (S)-1-(ethylsulfinyl)-4-methylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: diethylmagnesium With n-butyllithium; (S)-[1,1']-binaphthalenyl-2,2'-diol In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: di(p-tolyl) sulfoxide In tetrahydrofuran; diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere;
  • 59
  • [ 1774-35-2 ]
  • [ 2892-94-6 ]
  • [ 77919-66-5 ]
YieldReaction ConditionsOperation in experiment
86% In tetrahydrofuran; diethyl ether at 0℃; for 1.5h; Inert atmosphere;
  • 60
  • [ 1774-35-2 ]
  • [ 536-74-3 ]
  • 2-(5-methyl-2-(p-tolylthio)phenyl)-1-phenylethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With trifluorormethanesulfonic acid In neat (no solvent) at 100℃; for 1.5h; Inert atmosphere;
  • 61
  • [ 1774-35-2 ]
  • [ 1449549-02-3 ]
  • m-tolyl 2-(5-methyl-2-(p-tolylthio)phenyl)hexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With trifluorormethanesulfonic acid In neat (no solvent) at 70℃; for 6h;
  • 62
  • [ 1774-35-2 ]
  • [ 3085-42-5 ]
  • [ 1449549-02-3 ]
  • m-tolyl 2-(5-methyl-2-(p-tolylthio)phenyl)hexanoate [ No CAS ]
  • m-tolyl 2-(5-chloro-2-((4-chlorophenyl)thio)phenyl)hexanoate [ No CAS ]
  • 63
  • [ 825-55-8 ]
  • [ 1774-35-2 ]
  • bis(4-methylphenyl)(5-phenyl-thiophen-2-yl)sulfonium hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98.6% Stage #1: 2-phenylthiophene; di(p-tolyl) sulfoxide With methanesulfonic acid; acetic anhydride at 0 - 10℃; for 1h; Stage #2: With potassium hexafluorophosphate In water; chlorobenzene at 40 - 50℃; for 1h; 1 Example 1 A stirrer, a thermometer and a cooler with a volume of 100 ml flask in four port, bis (4-methylphenyl) sulfoxide 4. 6g (0. Aminothiophene 020 mol.), 2-3. 2g (0. 020 mol.) 10 and acetic anhydride. 2g (0. 100 mol) a ketone, while keeping the temperature inside 0-10 ° C, methansulfonate 7. 7g (0. 080 mol.) dropped to 1 hour. 3 while maintaining the same temperature even after the completion of the dropping time and then, by further stirred at room temperature for 4 hours, a condensation product of a reaction solution is obtained.A stirrer, a thermometer and a cooler with a four port 200 ml flask in volume, potassium phosphate hexafluoroisopropylether 3. 7g (0. 020 mol.), water 60g, and a monochloro benzene 20g, 30 minutes while maintaining the temperature in the reaction 30-50 ° C by dropping into the whole amount of the solution. Furthermore, after 30 minutes under stirring 40-50 ° C, by which the layer monochloro benzene, 50g 5% NaHCO3 aq. 40-50 ° C 30 is added with stirring. Again taking monochloro benzene layer, yellowish brown monochloro benzene by distilling the concentrate of 9. 5g is obtained.This concentrate ethyl acetate 40g is added by crystallization, bis (4-methylphenyl) (5-phenyl-thiophenalkyl-2-yl) dimethylsulfonium hexafluoroisopropylether phosphate of yellowish white crystal 8. 2g (0. 016 mol.) is obtained. The purity bis (4-methylphenyl) (5-phenyl-thiophenalkyl-2-yl) dimethylsulfonium hexafluoroisopropylether obtd. of phosphate, result measured by high speed liquid chromatography, 98. 6%. Furthermore, the yield aminothiophene phenylpropionic 79%.
  • 64
  • [ 1774-35-2 ]
  • [ 4187-87-5 ]
  • (E)-2-(5-methyl-2-(p-tolylthio)phenyl)-3-phenylacrylaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With trifluorormethanesulfonic acid In nitromethane at 80℃; for 3h;
  • 65
  • [ 37614-59-8 ]
  • [ 1774-35-2 ]
  • 1-(4-methoxyphenyl)-2-(5-methyl-2-(p-tolylthio)phenyl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With trifluorormethanesulfonic acid In nitromethane at 100℃; for 4h;
  • 66
  • [ 1774-35-2 ]
  • [ 1817-49-8 ]
  • (E)-2-(5-methyl-2-(p-tolylthio)phenyl)-1,3-diphenylprop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With trifluorormethanesulfonic acid In nitromethane at 50℃; for 4.5h;
  • 67
  • [ 1774-35-2 ]
  • [ 3085-42-5 ]
  • [ 135-19-3 ]
  • C22H14Cl2OS [ No CAS ]
  • C24H20OS [ No CAS ]
  • 68
  • [ 1774-35-2 ]
  • [ 135-19-3 ]
  • C24H20OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In acetonitrile at 0℃; for 3h; Green chemistry;
  • 69
  • [ 1774-35-2 ]
  • [ 135-19-3 ]
  • C24H20OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: di(p-tolyl) sulfoxide; β-naphthol With trifluoromethylsulfonic anhydride In acetonitrile at 0℃; for 3h; Green chemistry; Stage #2: With potassium phosphate In water at 70℃; for 24h; Micellar solution; Green chemistry;
  • 70
  • [ 1774-35-2 ]
  • [ 217813-03-1 ]
  • (2-methoxy-6-(3-methoxyphenoxy)phenyl)di-p-tolylsulfonium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With cesium fluoride In acetonitrile at 25℃; for 16h; Inert atmosphere; Glovebox;
  • 71
  • [ 1774-35-2 ]
  • [ 717903-52-1 ]
  • (6-(benzo[d][1,3]dioxol-5-yloxy)benzo[d][1,3]dioxol-5-yl)di-p-tolylsulfonium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With cesium fluoride In acetonitrile at 25℃; for 16h; Inert atmosphere; Glovebox;
  • 72
  • [ 1774-35-2 ]
  • [ 217813-00-8 ]
  • (2-(3,4-difluorophenoxy)-4,5-difluorophenyl)di-p-tolylsulfonium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With cesium fluoride In acetonitrile at 25℃; for 16h; Inert atmosphere; Glovebox;
  • 73
  • [ 1774-35-2 ]
  • [ 88284-48-4 ]
  • (2-phenoxyphenyl)di-p-tolylsulfonium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With cesium fluoride In acetonitrile at 25℃; for 9h; Inert atmosphere; 8 Example 8 At room temperature,Vacuum was carried out in a 25 mL reaction tube,For three times,Under nitrogen protection, cesium fluoride was added to 91.1 mg (0.6 mmol)And acetonitrile (3 mL),Then, 69.1 mg (0.3 mmol) of 4,4'-xylene sulfoxide was added,Finally, 89.5 mg (0.3 mmol) of phenylene precursor was added,The reaction was carried out at 25 ° C.The reaction process was tracked by thin layer chromatography,The developing agent was a dichloromethane / methanol having a volume ratio of 15: 1,The reaction time was 9 h. After the reaction was completed, the reaction mass was filtered through a column chromatography columnCesium fluoride, concentrated in vacuo and isolated by column chromatography to give the desired product in a yield of 97%.
96% With cesium fluoride In acetonitrile at 25℃; for 16h; Inert atmosphere; Glovebox;
96% With cesium fluoride In acetonitrile at 20℃; for 72h; Inert atmosphere; Glovebox;
  • 74
  • [ 1126-79-0 ]
  • [ 1774-35-2 ]
  • bis(4-methylphenyl)(4-butoxyphenyl)sulfonium hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.6% Stage #1: n-butyl phenyl ether; di(p-tolyl) sulfoxide With aluminum (III) chloride; methanesulfonic acid; sulfuric acid at 5 - 15℃; for 6h; Stage #2: With potassium hexafluorophosphate In water; chlorobenzene at 25 - 35℃; for 1h; 4 Preparation of bis(4-methylphenyl)(4-butoxyphenyl)sulfonium hexafluorophosphate In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 23.0 g (0.10 mol) of bis (4-methylphenyl) sulfoxide, 16.5 g (0.11 mol) of butoxybenzene, 28.8 g (0.30 mol) of methanesulfonic acid and 0.08 g (0.0006 mol) of aluminum chloride were charged, while maintaining the internal temperature at 5 °C to 15 °C, 30.3 g (0.30 mol) of concentrated sulfuric acid was added dropwise over 2 hours. After completion of the dropwise addition, while stirring at the same temperature for 4 hours, to obtain a reaction solution of the condensation reaction product. The reaction rate of bis (4-methylphenyl)sulfoxide was 98.5%. Into a 500 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 19.3 g (0.105 mol) of potassium hexafluorophosphate, 100 g of water and 100 g of monochlorobenzene were charged, while maintaining the internal temperature at 25° Cto 35 ° C, the whole amount of the reaction solution was added dropwise over 30 minutes. Further, after stirring at 30 to 35 ° C. for 30 minutes, The monochlorobenzene layer was separated. Subsequently, the obtained monochlorobenzene layer was washed with 50 g of water, and monochlorobenzene was distilled off to obtain 49.1 g of a pale yellow concentrate. The yield of bis(4-methylphenyl)(4-butoxyphenyl)sulfonium hexafluorophosphate relative to bis(4-methylphenyl)sulfoxide was 96.6%, the purity by HPLC analysis was 97.5%.
  • 75
  • [ 1774-35-2 ]
  • [ 103-73-1 ]
  • bis(4-methylphenyl)(4-ethoxyphenyl)sulfonium hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: di(p-tolyl) sulfoxide; Phenetole With aluminum (III) chloride; methanesulfonic acid; sulfuric acid at 5 - 15℃; for 6h; Stage #2: With potassium hexafluorophosphate In water; chlorobenzene at 25 - 35℃; for 1h; 6 Preparation of bis(4-methylphenyl)(4-ethoxyphenyl)sulfonium hexafluorophosphate In a 100 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 23.0 g (0.10 mol) of bis(4-methylphenyl)sulfoxide, 13.4 g (0.11 mol) of ethoxybenzene, 28.8 g (0.30 mol) of methanesulfonic acid and 0.08 g (0.0006 mol) of aluminum chloride were charged, while maintaining the internal temperature at 5 °Cto 15 °C, 30.3 g (0.30 mol) of concentrated sulfuric acid was added dropwise over 2 hours. After completion of the dropwise addition, the mixture was stirred for 4 hours while maintaining the same temperature, to obtain a reaction solution of the condensation reaction product. The reaction rate of bis(4-methylphenyl) sulfoxide was 99.2%. In a 500 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 19.3 g (0.105 mol) of potassium hexafluorophosphate, 100 g of water and 100 g of monochlorobenzene were charged, and the whole amount of the reaction solution was added dropwise over 30 minutes while maintaining the internal temperature at 25 to 35 ° C. Further, after stirring at 30 to 35 ° C. for 30 minutes, the monochlorobenzene layer was separated. Subsequently, the resultant monochlorobenzene layer was washed with 50 g of water, and then monochlorobenzene was distilled off to obtain 46.1 g of a pale yellow concentrate. The yield of bis(4-methylphenyl) (4-ethoxyphenyl) sulfonium hexafluorophosphate relative to bis (4-methylphenyl) sulfoxide was 96.0% and the purity by HPLC analysis was 98.7% .
  • 76
  • [ 1092542-31-8 ]
  • [ 1774-35-2 ]
  • 3-bromo-2-(4-tolylthio)phenyl 4-tolyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With potassium fluoride; 18-crown-6 ether In 1,4-dioxane at 110℃; for 20h; Inert atmosphere; regioselective reaction;
  • 77
  • [ 1774-35-2 ]
  • [ 217813-03-1 ]
  • 3-methoxy-2-(4-tolylthio)phenyl 4-tolyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium fluoride; 18-crown-6 ether In 1,4-dioxane at 110℃; for 30h; Inert atmosphere; regioselective reaction;
  • 78
  • [ 1774-35-2 ]
  • [ 217813-03-1 ]
  • (2-methoxy-6-(3-methoxyphenoxy)phenyl)di-p-tolylsulfonium trifluoromethanesulfonate [ No CAS ]
  • 3-methoxy-2-(4-tolylthio)phenyl 4-tolyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 63% 2: 8% With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 60℃; for 20h; Inert atmosphere; regioselective reaction;
  • 79
  • [ 1774-35-2 ]
  • [ 73183-34-3 ]
  • [ 195062-57-8 ]
YieldReaction ConditionsOperation in experiment
76% With chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); lithium hexamethyldisilazane In tetrahydrofuran at 80℃; for 20h; Schlenk technique; Inert atmosphere; Double Borylation of Diaryl Sulfoxides 1 (Table 2); Typical Procedure General procedure: A Schlenk tube was charged with diphenyl sulfoxide (1a) (41 mg, 0.20mmol), SPhos Pd G2 (7.2 mg, 0.010 mmol), B 2 pin 2 (0.20 g, 0.80 mmol),and LiN(SiMe 3 ) 2 (0.20 g, 1.2 mmol). THF (0.80 mL) was added to thetube and the resulting mixture was stirred at 80 °C for 20 h. After thereaction was complete, saturated aqueous NH 4 Cl (2 mL) was addedand the resulting biphasic mixture was extracted with Et 2 O (5 × 5mL). The combined organic layer was dried over Na 2 SO 4 , passedthrough a pad of silica gel, and concentrated under reduced pressure.The residue was purified by preparative TLC (hexane/EtOAc = 10:1) toprovide (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (2a)(54 mg, 0.26 mmol, 66%) as a colorless oil. All the resonances in the 1 Hand 13 C NMR spectra were consistent with the reported data. 12a
  • 80
  • [ 1774-35-2 ]
  • [ 2294-79-3 ]
  • C45H44S2(2+)*2Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With aluminum (III) chloride In dichloromethane at 0 - 10℃; for 26h; 3.1 Example 3 (1) Preparation of Intermediate 3a Into a 500 mL four-necked flask, 22 g of starting material 3a, aluminum trichloride 28 g, and dichloromethane 50 mL were added, and the water bath was cooled to 0.°C. Dissolve 46 g of the raw material 3b in 100 mL of methylene chloride, and then add it to a dropping funnel to control the temperature to 10° C. or lower. Add a mixed solution of the starting material 3 b and methylene chloride dropwise to the four-necked flask, which is added dropwise over about 2 hours. After continuous stirring for 24 hours, the liquid phase was traced until the raw material was no longer changed. The material was then slowly poured into 200 g of deionized water, stirred, solid precipitated, and filtered to obtain a light yellow solid, which was dried in an oven at 80° C. for 2 hours to obtain 56 g of intermediates. 3a, yield 65%, purity 98%.
  • 81
  • [ 1774-35-2 ]
  • [ 106-49-0 ]
  • [ 620-93-9 ]
YieldReaction ConditionsOperation in experiment
98% With SingaCycle-A1; sodium t-butanolate In tetrahydrofuran at 60℃; for 4h; Inert atmosphere; regioselective reaction;
  • 82
  • [ 1774-35-2 ]
  • butyl (hex-1-yn-1-yl) selenide [ No CAS ]
  • C24H32OSSe [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With trifluorormethanesulfonic acid In dichloromethane at 25℃; for 14h; Schlenk technique; Inert atmosphere; Darkness;
  • 83
  • [ 1774-35-2 ]
  • [ 68001-64-9 ]
  • C26H28OSSe [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With trifluorormethanesulfonic acid In dichloromethane at 25℃; for 14h; Schlenk technique; Inert atmosphere; Darkness;
  • 84
  • [ 911820-09-2 ]
  • [ 123726-16-9 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
91% With potassium hydroxide In water; toluene at 20℃; for 24h; Sealed tube; Inert atmosphere;
  • 85
  • [ 106-45-6 ]
  • [ 53188-52-6 ]
  • [ 1774-35-2 ]
YieldReaction ConditionsOperation in experiment
70% With air In water; acetonitrile at 20℃; for 16h; Irradiation;
70% In water; acetonitrile at 25℃; for 16h; Irradiation; 30 Experimental Example 30 In a 15 mL reaction tube,Add p-methylphenylazomethylsulfone 1b (0.6 mmol) in turn,p-Methylthiophenol 2b (0.2 mmol), 1 mL of acetonitrile and 1 mL of water,Mix evenly, then under the illumination of 3W blue LED light,The reaction was stirred at 25 ° C for 16 h. After the reaction was completed by TLC, the mixture was extracted with ethyl acetate, 3 mL each time, extracted three times, and the extracts were combined.After the extract is dried over anhydrous sodium sulfate,The extract was concentrated under reduced pressure in vacuo (0.08 Mpa) to dryness to afford crude material.Then rinse with a mixed eluent of 5:1 by volume of petroleum ether and ethyl acetate.Flash column chromatography on silica gel to obtain the sulfoxide product of this example.It was 32.2 mg of a yellow oily solid, yield 70%.
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