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Chemistry
Organic Building Blocks
Sulfides
Thianthrene 5-oxide
Chemistry
Organic Building Blocks
Sulfides
Benzene Compounds

[ CAS No. 2362-50-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2362-50-7
Chemical Structure| 2362-50-7
Structure of 2362-50-7 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 2362-50-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 2362-50-7 ]

Product Details of [ 2362-50-7 ]

CAS No. :2362-50-7 MDL No. :MFCD01464038
Formula : C12H8OS2 Boiling Point : -
Linear Structure Formula :- InChI Key :NYVGTLXTOJKHJN-UHFFFAOYSA-N
M.W : 232.32 Pubchem ID :73220
Synonyms :

Calculated chemistry of [ 2362-50-7 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.82
TPSA : 61.58 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 2.85
Log Po/w (WLOGP) : 4.18
Log Po/w (MLOGP) : 3.41
Log Po/w (SILICOS-IT) : 2.77
Consensus Log Po/w : 3.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.67
Solubility : 0.0499 mg/ml ; 0.000215 mol/l
Class : Soluble
Log S (Ali) : -3.8
Solubility : 0.0367 mg/ml ; 0.000158 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.04
Solubility : 0.0021 mg/ml ; 0.00000906 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.18

Safety of [ 2362-50-7 ]

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 [ 2362-50-7 ]

* 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 [ 2362-50-7 ]

[ 2362-50-7 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 92-85-3 ]
  • [ 2362-50-7 ]
YieldReaction ConditionsOperation in experiment
95% With nitric acid; In water; acetic acid; for 0.5h;Heating / reflux; To a solution of thianthrene (10.0 g 46.2 mmole) in glacial acetic acid (160 mL), [HN03] (5.8 [ML)] in water (12.6 mL) was added through the top of the condenser. The color immediately changed to pink and eventually yellow. The reaction mixture was refluxed for an additional half hour and then poured into ice water (600 mL). White precipitate was formed and collected by filtration. The precipitate was redissolved in [CH2CK,] washed with water, and dried with [MGS04. THE] solvent was removed in vacuo to yield white powder (10.7 g, 95%)
94% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0℃; for 1h;Inert atmosphere; The starting material, thianthrene (10.0 g, 46.2 mmol) and CH 2 Cl 2 (150 ml) were added to the round bottom flask and purged with nitrogen, and mCPBA (8.7 g, 50.8 ml) was dissolved in CH 2 Cl 2 The solution is added dropwise and stirred for 1 hour. After the reaction is complete, the reaction mixture is extracted with aqueous NaHCO 3 and CH 2 Cl 2. Then, the organic layer was dried with MgSO 4 and concentrated to obtain 10.0 g of thianthrene 5-oxide (yield: 94%).
93% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1h;Cooling with ice; Inert atmosphere; A soln of MCPBA (878 mg, 5.08 mmol) in CH2Cl2 (15 mL) was added to a stirred solution of thianthrene (1; 1.0 g, 4.62 mmol) in CH2Cl2 (15 mL) cooled in an ice bath under N2. After 1 h, the mixture was extracted with sat. aq NaHCO3 (3 × 15 mL). The organic layer was washed with H2O (2 × 25 mL) then dried (MgSO4) and concentrated under vacuum. The solid product was purified by TLC [silica gel, EtOAc-hexane (1:1)] to give colorless crystals; yield: 998 mg (93%);
93% With melamine-(H2SO4)3; C3H6N6*3HNO3; water; potassium bromide; In neat (no solvent); General procedure: Melamine-(H2SO4)3 [(0.21 g, 0.5 mmol)] and melamine-(HNO3)3 [(0.16 g, 0.5 mmol)], KBr[(0.0095 g, 0.1 mmol)] and few drops of water were mixed with the substrate [Table 1, Entries12-21, (1 mmol)] and ground in a mortar and pestle for 5 min. The mixture was changed toa black paste. The completion of the reaction was monitored by TLC. Then the product wasextracted with boiling chloroform (2 × 10 mL) and dried with 5 g Na2SO4 and filtered off.CHCl3 was removed by simple distillation and crude products were obtained with high purity.
92% With dihydrogen peroxide; In neat (no solvent); at 20℃; for 1.16667h;Green chemistry; General procedure: The sulfide (1mmol) was added to a mixture of 30% H2O2 (2.4 equiv, 1g) and MNPs-DABCO tribromide (10mg), and the mixture was stirred at room temperature for the time specified. The progress was monitored by TLC (EtOAc/n-hexane, 1/10). After completion of the reaction, the catalyst was separated from the product by an external magnet (within 5s) and the mixture was washed with Et2O (2×5mL) and decanted. The combined organics were dried over anhydrous Na2SO4 and then evaporation of diethyl ether under reduced pressure gave the pure products in 80-97% yields.
92% With 1,1?-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octane-1,4-diium) bis(hydrogen sulfate) dinitrate; potassium bromide; In neat (no solvent); at 20℃; for 0.5h;Green chemistry; General procedure: A mixture of an sulfide (1 mmol), [C4(DABCO-H)2]·[HSO4]2[NO3]2(0.5 mmol) and KBr (0.05 mmol) was vigorously grind using a mortarand pestle at roomtemperature. After completion of the reaction (monitoredby TLC), 5 mL water was added to the mortar and the mixturewas filtered to separate the nitrated product. The products were purifiedwith short column chromatography.
90% With peracetic acid; In acetic acid; at 110 - 120℃; for 4h; Thianthrene (5. 0G, 0. 023MOL) was added to acetic acid (40ML), stirred and heated to 110C- 120C until completely dissolved. An excess of peracetic acid (4. 4G, 0. 058MOL) was then added dropwise and the reaction mixture continuously stirred at this temperature for four hours. The reaction was followed using thin layer chromatography (TLC) using hexane: diethyl ether (80: 20 by volume) as an indication of thianthrene consumption because thianthrene and the sulphoxide have very distinct and separate spots/rf values. After cooling, the reaction mixture was poured into water (80ML), the resulting white precipitate filtered off, washed with water and dried in a vacuum oven at 50C for 4 hours. Product yield 4. 8g (90%) of white crystals. The product was analysed by IR, LCMS and HPLC. IR: 1078CM''AND 1029CM''S=0 due to sulphoxide. MS: MIT 233 (Mw of cation). HPLC: one very strong peak due to product, with a change in retention time and a shift in the characteristic chromophore compared to the starting material.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 1057 - 1064
[2]Tetrahedron,1991,vol. 47,p. 3773 - 3778
[3]Journal of Organic Chemistry,1995,vol. 60,p. 3172 - 3183
[4]Journal of the Chinese Chemical Society,2008,vol. 55,p. 1191 - 1194
[5]Letters in Organic Chemistry,2009,vol. 6,p. 335 - 339
[6]Journal of the Brazilian Chemical Society,2010,vol. 21,p. 33 - 36
[7]Journal of Organic Chemistry,2016,vol. 81,p. 129 - 136
[8]Monatshefte fur Chemie,2009,vol. 140,p. 65 - 68
[9]Journal of the Chinese Chemical Society,2009,vol. 56,p. 251 - 254
[10]Journal of the Iranian Chemical Society,2010,vol. 7,p. 190 - 194
[11]Cuihua Xuebao/Chinese Journal of Catalysis,2010,vol. 31,p. 1347 - 1350
[12]Synthesis,1997,p. 1161 - 1164
[13]Organic Preparations and Procedures International,1996,vol. 28,p. 705 - 708
[14]Patent: WO2003/101955,2003,A2 .Location in patent: Page 84
[15]Journal of the Iranian Chemical Society,2011,vol. 8,p. 142 - 148
[16]Patent: KR2019/63717,2019,A .Location in patent: Paragraph 0074; 0091-0094
[17]Synthesis,2014,vol. 46,p. 42 - 48
[18]Journal of Sulfur Chemistry,2015,vol. 36,p. 606 - 612
[19]Synthesis,1993,p. 1057 - 1058
[20]Monatshefte fur Chemie,2008,vol. 139,p. 895 - 899
[21]Catalysis Communications,2014,vol. 43,p. 16 - 20
[22]Journal of Molecular Liquids,2018,vol. 265,p. 517 - 524
[23]Synthesis,1995,p. 1357 - 1358
[24]Patent: WO2004/55000,2004,A1 .Location in patent: Page 45-46
[25]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 193 - 203
[26]Tetrahedron,2007,vol. 63,p. 7708 - 7716
[27]Synthetic Communications,1987,vol. 17,p. 515 - 520
[28]Tetrahedron Letters,2006,vol. 47,p. 2479 - 2483
[29]Crystal Growth and Design,2012,vol. 12,p. 2969 - 2977
[30]Tetrahedron Letters,1991,vol. 32,p. 793 - 796
[31]Chemistry - An Asian Journal,2019,vol. 14,p. 3370 - 3379
[32]Patent: WO2020/94673,2020,A1 .Location in patent: Page/Page column 26; 27
[33]New Journal of Chemistry,2002,vol. 26,p. 1448 - 1455
[34]Chemistry of Heterocyclic Compounds,1997,vol. 33,p. 333 - 337
[35]Journal of Organic Chemistry,2005,vol. 70,p. 301 - 308
[36]Bulletin of the Chemical Society of Japan,1982,vol. 55,p. 546 - 550
[37]Inorganic Chemistry,2013,vol. 52,p. 5418 - 5427
[38]Journal of the Chemical Society. Perkin transactions II,1981,p. 382 - 387
[39]Journal of Organic Chemistry,1993,vol. 58,p. 2035 - 2042
[40]Bulletin of the Chemical Society of Japan,1984,vol. 57,p. 2526 - 2530
[41]Journal of Organic Chemistry,1995,vol. 60,p. 4475 - 4480
[42]Justus Liebigs Annalen der Chemie,1915,vol. 407,p. 209
[43]Journal of the American Chemical Society,1955,vol. 77,p. 3387
[44]Journal of the American Chemical Society,1956,vol. 78,p. 2163
[45]Journal of the American Chemical Society,1956,vol. 78,p. 2163
[46]Journal of the Chemical Society,1910,vol. 97,p. 2590
[47]Journal of the American Chemical Society,1991,vol. 113,p. 6209 - 6212
[48]Journal of the Chemical Society. Perkin transactions II,1981,p. 382 - 387
[49]Canadian Journal of Chemistry,1994,vol. 72,p. 2249 - 2254
[50]Journal of Organic Chemistry,1995,vol. 60,p. 4475 - 4480
[51]Angewandte Chemie - International Edition in English,2000,vol. 39,p. X204-207
[52]Tetrahedron,2001,vol. 57,p. 2469 - 2476
[53]Chemistry - A European Journal,2007,vol. 13,p. 639 - 648
[54]Organic Letters,2011,vol. 13,p. 142 - 145
[55]Dalton Transactions,2010,vol. 39,p. 5509 - 5518
[56]Angewandte Chemie - International Edition,2011,vol. 50,p. 7321 - 7324
[57]Tetrahedron Letters,2013,vol. 54,p. 4918 - 4921
[58]RSC Advances,2017,vol. 7,p. 44259 - 44264
  • 2
  • [ 2362-50-7 ]
  • [ 92-85-3 ]
Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 259 - 260
[2]Tetrahedron Letters,1984,vol. 25,p. 341 - 344
[3]Journal of the Chemical Society. Perkin transactions I,1989,p. 1431 - 1435
[4]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 4351 - 4354
[5]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 3
  • [ 2362-50-7 ]
  • [ 951-02-0 ]
YieldReaction ConditionsOperation in experiment
97% With perchloric acid; TBA4[gamma-HPV2W10O40]; dihydrogen peroxide; In water; acetonitrile; tert-butyl alcohol; at 24.84℃; for 0.5h; General procedure: TBA4[gamma-HPV2W10O40](TBA = [(n-C4H9)4N]+, 1 mol), 70% aqueous perchloric acid (1 mol), 1a (1 mmol), and CH3CN/t-BuOH (1.5/1.5 mL) were charged in a reaction vessel. The reaction was initiated by addition of 30% aqueous H2O2 (1 mmol), and the reaction solution was periodically analyzed. Before the GC analysis,the remaining H2O2 was decomposed at 273 K by addition of Ru(OH)x/Al2O3
Reference： [1]Catalysis Today,2013,vol. 203,p. 76 - 80
[2]Journal of the Chemical Society. Perkin transactions I,1996,p. 2693 - 2698
[3]Synthetic Communications,1992,vol. 22,p. 1799 - 1806
[4]Tetrahedron Letters,1991,vol. 32,p. 793 - 796
[5]Tetrahedron Letters,1997,vol. 38,p. 2425 - 2426
[6]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 410 - 416
  • 4
  • [ 608-33-3 ]
  • [ 35787-71-4 ]
  • [ 2362-50-7 ]
  • [ 139656-63-6 ]
  • [ 92-85-3 ]
Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 2706 - 2710
  • 5
  • [ 13372-81-1 ]
  • [ 75-05-8 ]
  • [ 1006-67-3 ]
  • [ 4360-47-8 ]
  • [ 129610-15-7 ]
  • [ 2362-50-7 ]
  • [ 104-55-2 ]
Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1332 - 1334
  • 6
  • [ 35787-71-4 ]
  • [ 932-90-1 ]
  • [ 1199-00-4 ]
  • [ 1198-98-7 ]
  • [ 2362-50-7 ]
  • [ 100-52-7 ]
  • [ 100-47-0 ]
  • [ 92-85-3 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile for 48h; also in the presence of 2,6-di-tert-butyl-4-methylpyridine (before, 1h after or 12 h after reaction had been started);
Reference： [1]Chiou, Shishue; Hoque, A. K. M. M.; Shine, Henry J. [Journal of Organic Chemistry, 1990, vol. 55, # 10, p. 3227 - 3232]
  • 7
  • [ 35787-71-4 ]
  • [ 1129-37-9 ]
  • [ 1455-82-9 ]
  • [ 2362-50-7 ]
  • [ 555-16-8 ]
  • [ 92-85-3 ]
  • [ 619-72-7 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile also in the presence of 2,6-di-tert-butyl-4-methylpyridine;
Reference： [1]Chiou, Shishue; Hoque, A. K. M. M.; Shine, Henry J. [Journal of Organic Chemistry, 1990, vol. 55, # 10, p. 3227 - 3232]
  • 8
  • [ 2362-50-7 ]
  • [ 3808-86-4 ]
  • 4,6-Bis(2,5-xylylthio)thianthrene 5-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 3 h, 2.) -20 deg C, 12 h;
Reference： [1]Kimura, Takeshi; Ishikawa, Yasuhiro; Ueki, Kensaku; Horie, Yoji; Farukawa, Naomichi [Journal of Organic Chemistry, 1994, vol. 59, # 23, p. 7117 - 7124]
  • 9
  • [ 2362-50-7 ]
  • [ 2362-53-0 ]
Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 4475 - 4480
[2]Tetrahedron Letters,1997,vol. 38,p. 2425 - 2426
[3]Tetrahedron,2001,vol. 57,p. 2469 - 2476
[4]Chemistry - A European Journal,2007,vol. 13,p. 639 - 648
[5]Dalton Transactions,2010,vol. 39,p. 5509 - 5518
[6]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 410 - 416
  • 10
  • [ 2362-50-7 ]
  • [ 2362-53-0 ]
  • [ 2362-54-1 ]
Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 4280 - 4285
  • 11
  • [ 75-77-4 ]
  • [ 2362-50-7 ]
  • [ 135489-45-1 ]
YieldReaction ConditionsOperation in experiment
36% To a stirred solution of <strong>[2362-50-7]thianthrene-5-oxide</strong> (9.40 g, 40.5 mmole) in THF (200 mL), lithium diisopropylamide (prepared by the addition of n-butyl lithium (1.6 M, 64.0 mL, [101] mmole) to a solution [OF DIISOPROPYLAMINE] (14.2 mL, [101] mmole) [AT-78 C)] in THF (100 mL) was added in portion at-78 [C] under inert atmosphere. The reaction mixture was stirred at this temperature for 4 hrs and became dark green. [CHLOROTRIMETHYLSILANE] (12.8 mL, [101] mmole) was then added to the cold solution. The solution was then turned into yellowish brown, warmed back to room temperature, and stirred overnight. Water (100 mL) was then added to the reaction mixture to quench the excess base. The solvent was removed and the crude mixture was redissolved in ether. The aqueous layer was extracted by ether and the organic layers were combined. It was further washed by water, brine, and dried with [MGS04.] The solvent was then removed in vacuo. The crude product was further purified by column chromatography [(HEXANE/CH2CL2] 4/1, and then 2/1) to afford light yellow crystals (5.50 g, 36%). mp [210-211] [C] (lit. [213-214 C). H] NMR (300 MHz, [CDC13)] [S] : 7.69 (dd, [2H,] [J=] 7.8, 1.5 Hz), 7.60 (dd, 2H, [J=] 7. 8, 1.5 Hz), 7.41 (dd, 2H, [J=] 7.8, 7.8 Hz), 0.57 (s, 18H). 13C NMR (125 MHz, [CDC13)] [8] : 144.1, 140.9, 134.0, 133. 8, 129.9, 129.3, 1.55. HR-MS (ESI): calcd. for [C18H24OS2SI2+NA] 399.0699 [(M+Na)+]; found 399.0690.
Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 2479 - 2483
[2]Patent: WO2003/101955,2003,A2 .Location in patent: Page 84
  • 12
  • [ 2362-50-7 ]
  • [ 92-52-4 ]
  • C24H17S2(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.1% EXAMPLE 14; Thianthrene sulphoxide (2. 0g, 0. 0086moles), biphenyl (1.86g, 0.012moles), acetic acid (7ml), dichloromethane (1. 75ml) and acetic anhydride (7ml) were mixed in a round bottomed flask. A further 5ml of dichloromethane was added to dissolve the <strong>[2362-50-7]thianthrene sulphoxide</strong>. The temperature of the mixture was reduced to <15C using a water/ice bath. Concentrated sulphuric acid (2. 6ml) was then added drop wise, making sure the temperature did not exceed 15C. After the addition was complete, the mixture was stirred for 2 hours, allowing the temperature to increase to room temperature. 100ml of water was then added to the mixture. This was then extracted wih-200ml (2xlOOml) of dichloromethane. The dichloromethane was then dried with magnesium sulphate, filtered and removed on a rotary evaporator. This yielded 4. Og of intermediate product. This was dissolved in a minimum of acetic acid. The solution was then poured into a KPF6 solution (2g in 65ml water). The product produced was a solid that was collected by filtration and washed with water. Finally, the product was dried in a vacuum oven. Product yield 3.42g (77. 1 %) of a very pale pink solid. The product was analysed by HPLC, LC-MS and IR.
Reference： [1]Patent: WO2003/72567,2003,A1 .Location in patent: Page/Page column 26
  • 13
  • [ 2362-50-7 ]
  • [ 29420-49-3 ]
  • [ 108-95-2 ]
  • [ 1201658-36-7 ]
YieldReaction ConditionsOperation in experiment
6.12 g of methanesulfonic acid are added to 625 mg of phosphorus oxide, and the mixture is stirred for 1 hour until the phosphorus oxide is dissolved. To the solution, 1.12 g of phenol are added at room temperature, and the reaction mixture is stirred for 30 min. 2.02 g of thian- threne-9-oxide is added. The reaction mixture is stirred overnight at room temperature, and then is poured into an aqueous solution of <strong>[29420-49-3]potassium nonaflate</strong> (4.05 g / 80 ml). The product is <n="80"/>extracted with dichloromethane, and the organic layer is washed with brine and dried over anhydrous magnesium sulfate. After removal of the magnesium sulfate by filtration, the organic extracts are condensed to give a beige solid. The solid is dissolved in a mixture of di- chloromethane-methanol (10:1 ), and purification by column chromatography eluting mixture of dichloromethane-methanol (12:1 ) as a solvent to give 3.43 g of the compound of example 1.1 as an off-white powder. The structure is confirmed by the 1H-NMR. delta [ppm]: (DMSO-dbeta). delta [ppm]: 6.88 (d, 2H), 7.14 (d, 2H), 7.76 (td, 2H), 7.84 (td, 2H), 8.05 (dd, 2H), 8.39 (dd, 2H), 10.70 (br, 1 H).
Reference： [1]Patent: WO2009/150074,2009,A1 .Location in patent: Page/Page column 78-79
  • 14
  • [ 75-77-4 ]
  • [ 2362-50-7 ]
  • 1,9-bis(trimethylsilyl)thianthrene 5-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% A 1.8 M soln of LDA in THF (6.0 mL, 10.8 mmol) was added to a stirred solution of oxide 8 (1.0 g, 4.30 mmol) in THF (25 mL) at -78 C under N2. After 3 h, the mixture was warmed to r.t., stirred for 30 min, and then cooled to -30 C. TMSCl (1.41 g, 13.0 mmol) was added, and the mixture was stirred for 3 h. The reaction was quenched with H2O (15 mL), and CHCl3 (30 mL) was added. The organic layer was separated, washed successively with H2O (2 × 30 mL) and brine (2 × 20 mL), dried (MgSO4), and concentrated under vacuum to give a solid product. The product was purified by TLC [silica gel, EtOAc-hexane (1:3)] to give colorless crystals; yield: 1.04 g (64%);
Reference： [1]Synthesis,2014,vol. 46,p. 42 - 48
  • 15
  • [ 2362-50-7 ]
  • [ 407-25-0 ]
  • [ 131807-57-3 ]
  • C34H21F4N2O4S2(1+)*C2F3O2(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With Thianthrene In acetonitrile at -78 - 25℃;
Reference： [1]Berger, Florian; Plutschack, Matthew B.; Riegger, Julian; Yu, Wanwan; Speicher, Samira; Ho, Matthew; Frank, Nils; Ritter, Tobias [Nature, 2019, vol. 567, # 7747, p. 223 - 228]
  • 16
  • [ 2362-50-7 ]
  • [ 1601-18-9 ]
  • [ 407-25-0 ]
  • C32H21ClF4NO4S2(1+)*C2F3O2(1-) [ No CAS ]
Reference： [1]Nature,2019,vol. 567,p. 223 - 228
  • 17
  • [ 75-77-4 ]
  • [ 2362-50-7 ]
  • [ 176646-31-4 ]
YieldReaction ConditionsOperation in experiment
58% The <strong>[2362-50-7]thianthrene 5-oxide</strong> (10.0 g, 43.0 mmol) Was placed in THF (250 ml) and purged with nitrogen, LDA (1.8 M in THF, 60 ml, 108 mmol) was added dropwise at -78 deg. C, stirred for 4 hours, and then stirred at room temperature for 1 hour. TMSCl (14.1 g, 130 mmol) was added dropwise at -30 deg. C, followed by stirring for 3 hours. After the reaction was completed, the reaction mixture was extracted with CH 2 Cl 2 and the organic layer was dried over MgSO 4 and concentrated. after, The concentrate was passed through a silica gel column and recrystallized to obtain 9.0 g (yield: 58%) of 1,9-bis (trimethylsilyl) thianthrene.
Reference： [1]Patent: KR2019/63717,2019,A .Location in patent: Paragraph 0074; 0091; 0092; 0095
  • 18
  • [ 67969-82-8 ]
  • [ 2362-50-7 ]
  • [ 49562-28-9 ]
  • C32H28ClO4S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 14615 - 14619
    Angew. Chem.,2019,vol. 58,p. 14757 - 14761,5
  • 19
  • [ 67969-82-8 ]
  • [ 2362-50-7 ]
  • [ 6121-42-2 ]
  • C23H19O2S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With trifluoroacetic anhydride In acetonitrile at 0 - 23℃; for 12h;
Reference： [1]Ye, Fei; Berger, Florian; Jia, Hao; Ford, Joseph; Wortman, Alan; Börgel, Jonas; Genicot, Christophe; Ritter, Tobias [Angewandte Chemie - International Edition, 2019, vol. 58, # 41, p. 14615 - 14619][Angew. Chem., 2019, vol. 58, p. 14757 - 14761,5]
  • 20
  • [ 67969-82-8 ]
  • [ 39513-75-2 ]
  • [ 2362-50-7 ]
  • C22H17O2S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 16161 - 16166
    Angew. Chem.,2019,vol. 131,p. 16307 - 16312,6
  • 21
  • [ 67969-82-8 ]
  • [ 2362-50-7 ]
  • [ 15362-40-0 ]
  • C26H16Cl2NOS2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 16161 - 16166
    Angew. Chem.,2019,vol. 131,p. 16307 - 16312,6
  • 22
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • [ 827-52-1 ]
  • C24H23S2(1+)*CF3O3S(1-) [ No CAS ]
Reference： [1]Science China Chemistry,2020,vol. 63,p. 336 - 340
  • 23
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • [ 458-92-4 ]
  • C19H13F2OS2(1+)*CF3O3S(1-) [ No CAS ]
Reference： [1]Science China Chemistry,2019
  • 24
  • [ 92-53-5 ]
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • C22H20NOS2(1+)*CF3O3S(1-) [ No CAS ]
Reference： [1]Science China Chemistry,2020,vol. 63,p. 336 - 340
  • 25
  • [ 4641-57-0 ]
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • 5-(4-(2-oxopyrrolidin-1-yl)phenyl)-5H-thianthren-5-ium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In dichloromethane at -40 - 20℃; for 1h; Inert atmosphere;
In dichloromethane at -40 - 20℃; for 1h;
In dichloromethane at -40 - 20℃; Schlenk technique; Inert atmosphere;
In dichloromethane at -40 - 20℃; Inert atmosphere; Schlenk technique; 62 Example 62 Under a nitrogen atmosphere, a mono-substituted aromatic hydrocarbon substrate 8m (0.2 mmol), thioanthracene-S-oxide (0.24 mmol) was added to a 25 mL Schlenk tube, and DCM (1.0 mL) was added, followed by stirring at -40°C.After slowly dropping Tf2O (0.24 mmol), it was stirred at -40°C for 30 minutes, followed by stirring at room temperature for 1 hour.Then, under a nitrogen atmosphere, sodium bicarbonate (0.6 mmol), arylboronic acid substrate 4k (0.3 mmol), bis(tri-tert-butylphosphine) palladium (0.01 mmol), acetone (1.0 mL) was added, and the cap was screwed tightly. At room temperature for 12 hours.After the reaction was completed, a small amount of DCM was added to quench the reaction, the celite was filtered, and the solvent was removed under reduced pressure. The crude product was separated and purified by a preparation plate (DCM) to obtain a white solid 7m (43.0 mg) with a yield of 73%.
In dichloromethane at -40 - 20℃; for 1.5h; Schlenk technique; Inert atmosphere;
In dichloromethane at -40 - 20℃; for 0.333333h; Schlenk technique; Inert atmosphere; regioselective reaction;
In dichloromethane at -20 - 30℃; for 0.666667h; Schlenk technique; Inert atmosphere;

Reference： [1]Lin, Zeng-Hui; Tian, Ze-Yu; Zhang, Cheng-Pan [Organic Letters, 2021, vol. 23, # 11, p. 4400 - 4405]
[2]Wu, Jie; Wang, Zengwei; Chen, Xiao-Yue; Wu, Yichen; Wang, Daoming; Peng, Qian; Wang, Peng [Science China Chemistry, 2020, vol. 63, # 3, p. 336 - 340]
[3]Chen, Xiao-Yue; Nie, Xiao-Xue; Wu, Yichen; Wang, Peng [Chemical Communications, 2020, vol. 56, # 37, p. 5058 - 5061]
[4]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111187130, 2020, A Location in patent: Paragraph 0397-0399
[5]Chen, Xiao-Yue; Huang, Yu-Hao; Zhou, Jian; Wang, Peng [Chinese Journal of Chemistry, 2020, vol. 38, # 11, p. 1269 - 1272]
[6]Wu, Yichen; Huang, Yu-Hao; Chen, Xiao-Yue; Wang, Peng [Organic Letters, 2020, vol. 22, # 16, p. 6657 - 6661]
[7]Zhang, Yu-Lan; Wang, Gang-Hu; Wu, Yichen; Zhu, Chun-Yin; Wang, Peng [Organic Letters, 2021, vol. 23, # 21, p. 8522 - 8526]
  • 26
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • [ 95737-68-1 ]
  • C32H26NO3S2(1+)*CF3O3S(1-) [ No CAS ]
Reference： [1]Science China Chemistry,2020,vol. 63,p. 336 - 340
  • 27
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • [ 144432-80-4 ]
  • C30H28BO2S2(1+)*CF3O3S(1-) [ No CAS ]
Reference： [1]Science China Chemistry,2020,vol. 63,p. 336 - 340
  • 28
  • [ 2362-50-7 ]
  • [ 27607-77-8 ]
  • [ 100-58-3 ]
  • 5-phenyl-5H-thianthren-5-ium triflate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.9% In tetrahydrofuran; at 20℃; for 1h; Thianthrene-5-oxide (18.8 g, 81 mmol), and trimethylsilyl trifluoromethanesulfonate (36 g, 163 mmol) were dissolved in THF (47 g), and a phenylmagnesium bromide THF solution prepared by a conventional method using bromobenzene (12.7 g, 81 mmol), magnesium (2.0 g, 81 mmol), and THF (90 g) was added dropwise thereto so that the temperature in the system did not exceed -5 C. After dropwise addition was completed, the reaction continued at room temperature for 1 hour to complete the reaction. The reaction solution was put into ultra pure water (150 g) for 1 hour, and dichloromethane (170 g) was then added thereto, the mixture was stirred for 30 minutes and an aqueous layer was then removed. An organic layer was washed with ultra pure water (150 g) 3 times, the organic layer was then added dropwise to methyl tert-butyl ether (MTBE, 1700 g), and the precipitated solid was filtered off. The filtrate was dried under a reduced pressure to obtain an intermediate 1a (24.7 g, yield=68.9%).
Reference： [1]Patent: US2019/361345,2019,A1 .Location in patent: Paragraph 1061
  • 29
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 14850-23-8 ]
  • C20H23S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 30
  • [ 2362-50-7 ]
  • [ 14850-23-8 ]
  • [ 407-25-0 ]
  • C20H24S2(2+)*2C2F3O2(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 31
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 768-56-9 ]
  • C22H19S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 32
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 7736-25-6 ]
  • C25H20NO2S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 33
  • [ 300-57-2 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • C21H17S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 34
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 1813-97-4 ]
  • C22H16F3S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 35
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • (+)-tetrahydro-4-methyl-2-(2-methylpropenyl)-2H-pyran [ No CAS ]
  • C22H25OS2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 36
  • [ 110-87-2 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • C17H15OS2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 37
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 17150-61-7 ]
  • C23H20NOS2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 38
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 628-92-2 ]
  • C19H19S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 39
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 91465-71-3 ]
  • C23H23S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: thianthrene-5-oxide; tricyclo[6.2.1.0(2,7)]undeca-4-ene With trifluoroacetic acid; trifluoroacetic anhydride In acetonitrile at 0℃; for 1.5h; Inert atmosphere; Stage #2: sodium tetrafluoroborate In water regioselective reaction;
Reference： [1]Berger, Florian; Chen, Junting; Li, Jiakun; Plutschack, Matthew B.; Ritter, Tobias [Angewandte Chemie - International Edition, 2020, vol. 59, # 14, p. 5616 - 5620][Angew. Chem., 2020, vol. 132, # 14, p. 5665 - 5669,5]
  • 40
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • C20H17NO2 [ No CAS ]
  • C32H24NO2S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 41
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • C26H40O3 [ No CAS ]
  • C38H47O3S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 42
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 7642-15-1 ]
  • C20H23S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 43
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • C23H20F4N2O5S [ No CAS ]
  • C35H27F4N2O5S3(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 44
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 111-66-0 ]
  • C20H23S2(1+)*BF4(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 45
  • [ 2362-50-7 ]
  • [ 407-25-0 ]
  • [ 7642-15-1 ]
  • C20H24S2(2+)*2C2F3O2(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 5616 - 5620
    Angew. Chem.,2020,vol. 132,p. 5665 - 5669,5
  • 46
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • [ 456-55-3 ]
  • C19H12F3OS2(1+)*CF3O3S(1-) [ No CAS ]
Reference： [1]Chemical Communications,2020,vol. 56,p. 5058 - 5061
[2]Patent: CN111187130,2020,A .Location in patent: Paragraph 0389-0391
  • 47
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • [ 51803-78-2 ]
  • [ 2489621-35-2 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at -40 - 20℃; Schlenk technique; Inert atmosphere;
In dichloromethane at -40 - 20℃; Inert atmosphere; Schlenk technique; 85 Example 85 Under a nitrogen atmosphere, a mono-substituted aromatic hydrocarbon substrate 8aj (0.2 mmol), thioanthracene-S-oxide (0.24 mmol), and DCM (1.0 mL) were added to a 25 mL Schlenk tube in this order, followed by stirring at -40°C.After slowly dropping Tf2O (0.24 mmol), it was stirred at -40°C for 30 minutes, followed by stirring at room temperature for 1 hour.Then, under a nitrogen atmosphere, sodium bicarbonate (0.6 mmol), arylboronic acid substrate 4k (0.3 mmol), bis(tri-tert-butylphosphine) palladium (0.01 mmol), acetone (1.0 mL) was added, and the cap was screwed tightly. At room temperature for 12 hours.After the reaction was completed, a small amount of DCM was added to quench the reaction, the celite was filtered, and the solvent was removed under reduced pressure. The crude product was separated and purified by a preparation plate (DCM) to obtain 7aj (87.0 mg) as a white solid with a yield of 99%.
In dichloromethane at -40 - 20℃; for 1.5h; Schlenk technique; Inert atmosphere;
Reference： [1]Chen, Xiao-Yue; Nie, Xiao-Xue; Wu, Yichen; Wang, Peng [Chemical Communications, 2020, vol. 56, # 37, p. 5058 - 5061]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111187130, 2020, A Location in patent: Paragraph 0489-0491
[3]Chen, Xiao-Yue; Huang, Yu-Hao; Zhou, Jian; Wang, Peng [Chinese Journal of Chemistry, 2020, vol. 38, # 11, p. 1269 - 1272]
  • 48
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • [ 2142-01-0 ]
  • C27H18NO2S2(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at -40 - 20℃; Schlenk technique; Inert atmosphere;
In dichloromethane at -40 - 20℃; Inert atmosphere; Schlenk technique; 67 Example 67 Under a nitrogen atmosphere, a mono-substituted aromatic hydrocarbon substrate 8r (0.2 mmol), thioanthracene-S-oxide (0.24 mmol), DCM (0.2 mL) were added to a 25 mL Schlenk tube, followed by stirring at -40°C.After slowly dropping Tf2O (0.24 mmol), it was stirred at -40°C for 30 minutes, followed by stirring at room temperature for 1 hour.Then add sodium bicarbonate (0.6 mmol), arylboronic acid substrate 4k (0.3 mmol), bis(tri-tert-butylphosphine) palladium (0.01 mmol) under nitrogen atmosphere, add DMF (1.0 mL), and tighten the cap At 50 , the reaction was stirred for 12 hours.After the reaction was completed, a small amount of DCM was added to quench the reaction, the celite was filtered, the solvent was removed under reduced pressure, and the crude product was separated and purified by a preparation plate (hexane/DCM (3/2)) to obtain a white solid 7r (37.0mg), yield 51%.
In dichloromethane at -40 - 20℃; for 1.5h; Schlenk technique; Inert atmosphere;
Reference： [1]Chen, Xiao-Yue; Nie, Xiao-Xue; Wu, Yichen; Wang, Peng [Chemical Communications, 2020, vol. 56, # 37, p. 5058 - 5061]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111187130, 2020, A Location in patent: Paragraph 0417-0419
[3]Chen, Xiao-Yue; Huang, Yu-Hao; Zhou, Jian; Wang, Peng [Chinese Journal of Chemistry, 2020, vol. 38, # 11, p. 1269 - 1272]
  • 49
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 101-84-8 ]
  • [ 2362-50-7 ]
  • C24H17OS2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: tetrafluoroboric acid diethyl ether; diphenylether; thianthrene-5-oxide With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 6h; Stage #2: sodium tetrafluoroborate In dichloromethane; water Thianthrenium salt TT-1 Under ambient atmosphere, a 500 ml. round-bottom flask equipped with a magnetic stir bar was charged with diphenyl ether (7.0 ml_, 7.5 g, 44 mmol, 1.0 equiv.) and MeCN (0.10 L, c =0.44 M). Trifluoroacetic anhydride (12.2 ml_, 18.4 g, 87.8 mmol, 2.0 equiv.) was added at ambient temperature while stirring. After cooling to 0°C, thianthrene S-oxide (10.2 g, 43.9 mmol, 0.99 equiv.) was added in one portion, followed by the addition of HBF4-OEt2(13.2 ml_, 15.7 g, 97.0 mmol, 2.2 equiv.) in one portion. The mixture was stirred at 0 °C for 1 h, then at ambient temperature for 5 h. The reaction mixture was concentrated under reduced pressure, and subsequently diluted with DCM (300 ml_). The solution was poured onto a saturated aqueous NaHC03solution (300 ml_), and the layers were separated. The organic phase was washed with aqueous NaBF4solution (2 x 300 ml_, 10%), and with water (2 x 300 ml_). The organic phase was dried over MgS0 , and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / MeOH (1 :0-10:1 (v/v)) to afford 20 g (98%) of TT-1 as colorless foam.R/ = 0.46 (DCM / MeOH, 94:6 (v/v)).NMR Spectroscopy:1H NMR (500 MHz, MeCN-d3, 25 °C, d): 8.32 - 8.30 (m, 2H), 7.96 - 7.94 (m, 2H),7.89 - 7.85 (m, 2H), 7.81 - 7.78 (m, 2H), 7.43 - 7.40 (m, 2H), 7.27 - 7.23 (m, 2H), 7.04 - 7.02 (m, 2H), 6.99 - 6.98 (m, 2H).13C NMR {'H} (126 MHz, MeCN-d3, 25 °C, d): 163.1 , 155.6, 137.2, 136.0, 135.6, 131.6, 131.6, 131.4, 130.9, 126.4, 121.3, 120.0, 1 19.9, 1 16.7.19F NMR {1H} (471 MHz, MeCN-d3, 25 °C, d): -151 .4, -151.5.HRMS-ESI (m/z) calc’d. for C24H17OS2+[M - BF4]+, 385.071530; found, 385.071535; deviation: +0.01 ppm.
98% Stage #1: tetrafluoroboric acid diethyl ether; diphenylether; thianthrene-5-oxide With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 6h; Stage #2: sodium tetrafluoroborate In dichloromethane; water
1.22 g Stage #1: tetrafluoroboric acid diethyl ether; diphenylether; thianthrene-5-oxide With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 6h; Stage #2: sodium tetrafluoroborate In water
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 78-79
[2]Berger, Florian; Berger, Georg; Engl, Pascal S.; Häring, Andreas P.; Pérez-Bitrián, Alberto; Ritter, Tobias [Journal of the American Chemical Society, 2019]
[3]Ye, Yun; Zhu, Jie; Huang, Yinhua [Organic Letters, 2021, vol. 23, # 6, p. 2386 - 2391]
  • 50
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 82846-47-7 ]
  • C28H23O3S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; methyl 2-(3-phenoxybenzene)propionate With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 2.5h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water Schlenk technique; Thianthrenium salt TT-3 Under ambient atmosphere, a 50 mL Schlenk-tube equipped with a magnetic stir bar was charged with fenoprofen methyl ester (260 mg, 1 .01 mmol, 1 .00 equiv.), thianthrene S-oxide (236 mg, 1.02 mmol, 1 .00 equiv.), and MeCN (5.1 ml_, c = 0.20 M). After cooling to -40 °C, trifluoroacetic anhydride (0.42 ml_, 0.63 g, 3.0 mmol, 3.0 equiv.) was added while stirring.HBF4OEt2(0.28 ml, 0.33 g, 2.1 mmol, 2.0 equiv.) was added dropwise. The mixture was stirred at -40 °C for 30 min, then at ambient temperature for 2 h. The reaction mixture was added to a saturated aqueous NaHC03solution (50 ml_), and the aqueous phase was extracted with DCM (3 x 20 ml_). The organic phase was washed with aqueous NaBF4solution (30 ml_, 10%), dried over MgS0 , and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / MeOH (1 :0- 9:1 (v/v)) to afford 536 mg (95%) of TT-3 as white foam.R/ = 0.39 (DCM / MeOH, 94:6 (v/v)).NMR Spectroscopy:1H NMR (500 MHz, CDCI3, 25 °C, d): 8.47 (d, J = 6.8 Hz, 2H), 7.86 - 7.77 (m, 4H), 7.75 - 7.69 (m, 2H), 7.29 (t, J = 7.9 Hz, 1 H), 7.24 - 7.18 (m, 2H), 7.12 (d, J = 7.7 Hz,1 H), 6.96 - 6.89 (m, 3H), 6.84 (dd, J = 8.1 , 1 .5 Hz, 1 H), 3.68 (q, J = 7.2 Hz, 1 H), 3.62 (s, 3H), 1.44 (d, J = 7.2 Hz, 3H).13C NMR {1H} (126 MHz, CDCI3, 25 °C, d): 174.5, 162.3, 154.4, 143.2, 136.3, 135.0, 135.0, 130.5, 130.5, 130.4, 124.8, 1 19.8, 1 19.2, 1 19.1 , 1 19.0, 1 15.8, 52.3, 45.2, 18.6. 19F NMR {1H} (471 MHz, CDCI3, 25 °C, d): -151.1 , -151 .1.HRMS-ESI (m/z) calc’d. for C28H2303S2+[M - BF4]+, 471.108315; found, 471.108290; deviation: +0.05 ppm.
95% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; methyl 2-(3-phenoxybenzene)propionate With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 2.5h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 83; 84
[2]Berger, Florian; Berger, Georg; Engl, Pascal S.; Häring, Andreas P.; Pérez-Bitrián, Alberto; Ritter, Tobias [Journal of the American Chemical Society, 2019]
  • 51
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 89-83-8 ]
  • C22H21OS2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; thymol With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Sealed tube; Stage #2: sodium tetrafluoroborate In dichloromethane; water Thymol-derived thianthrenium salt 20-TT Under ambient atmosphere, a 20 ml. borosilicate vial was charged with thymol (300 mg,2.00 mmol, 1.00 equiv.), thianthrene-S-oxide (466 mg, 2.00 mmol, 1.00 equiv.) and dry MeCN (8.0 ml_, c = 0.25 M). After cooling to 0 °C, HBF4OEt2(348 mI_, 2.40 mmol, 1.20 equiv.) was added in one portion at 0 °C, followed by trifluoroacetic anhydride (840 mI_, 1.27 g, 6.00 mmol, 3.00 equiv.) addition at 0 °C in one portion. The vial was sealed with a screw-cap, and the orange solution was allowed to stand at 0 °C for 1 h, followed by warming the reaction mixture to 25 °C over a period of 1 h. After stirring at 25 °C for 1 h further, the resulting beige solution was concentrated under reduced pressure, and diluted with 10 ml. CH2CI2. The CH2CI2solution was poured onto a saturated aqueous NaHC03solution (ca. 10 ml_). The mixture was poured into a separatory funnel, and the layers were separated. The CH2CI2layer was collected, and the aqueous layer was further extracted with CH2CI2(2 x ca. 10 ml_). The combined CH2CI2solution was washed with aqueous NaBF4solution (2 x ca. 20 ml_, 5 % w/w). The CH2CI2layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2//-PrOH (50:1 , v/v). The product was dissolved in 2 ml. CH2CI2, and precipitated with 10 ml. Et20. The suspension was decanted, and the solid was dried in vacuo to afford 20-TT (714 mg, 1 .58 mmol, 79 %) as a colorless solid.Rf= 0.35 (CH2CI2/MeOH, 15:1 , v/v).NMR Spectroscopy:1H NMR (500 MHz, CD2CI2, 298 K, d): 7.92 (d, J = 7.9 Hz, 2H), 7.77 (td, J = 7.6, 1 .5 Hz,2H), 7.72 (d, J = 7.7 Hz, 2H), 7.67 (td, J = 7.7, 1 .2 Hz, 2H), 7.21 (s, 1 H), 6.99 (s, 1 H), 3.22 (p, J = 6.9 Hz, 1 H), 2.54 (s, 3H), 1.05 (d, J = 7.0 Hz, 6H) ppm.13C NMR (126 MHz, CD2CI2, 298 K, d): 161.5, 142.5, 137.7, 135.2, 134.2, 131 .0, 130.9, 130.4, 130.3, 122.8, 120.8, 106.3, 27.2, 22.0, 20.1 ppm.19F NMR (471 MHz, CD2CI2, 298 K, d): -150.74(bs), -150.79(bs) ppm.HRMS-ESI (m/z) calculated for C22H210iS2+[M-BF4]+, 365.102835; found, 365.103090;deviation: -0.70 ppm
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 103
  • 52
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 6609-56-9 ]
  • C20H14NOS2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Under an ambient atmosphere, a 20-mL glass vial was charged with <strong>[6609-56-9]2-methoxy-benzonitrile</strong> (266 mg, 2.00 mmol, 1 .00 equiv) and MeCN (3.0 mL, c = 0.67 M). After cooling to 0 C, HBF4OEt2(0.34 mL, 0.40 g, 2.4 mmol, 1.2 equiv) and thianthrene-S-oxide (464 mg, 2.00 mmol, 1.00 equiv) was added to the vial while stirring the mixture, leading to a suspension. Subsequently, trifluoroacetic anhydride (0.84 mL, 1 .3 g, 6.0 mmol, 3.0 equiv) was added in one portion at 0 C, resulting in a color change to deep purple. Subsequently, the reaction mixture was allowed to reach 23 C and stirred for 12 hours. The solution was diluted with DCM (5 mL) and poured onto a mixture of DCM (30 mL) and saturated aqueous NaHC03solution (20 mL). After stirring for 5 min at 23 C, the mixture was poured into a separating funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (10% w/w, 4cca. 20 mL). The DCM layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (30:1 (v/v)), then the solvent was removed in vacuo to afford 13-TT (770 mg, 90% yield) as a colorless solid.R/ = 0.35 (DCM/MeOH, 15:1 , v/v).NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 25 C, d): 8.32 (dd, J = 8.0, 1.4 Hz, 2H), 7.95 (dd, J = 7.9, 1 .4 Hz, 2H), 7.87 (td, J = 7.7, 1 .4 Hz, 2H), 7.79 (td, J = 7.7, 1.4 Hz, 2H), 7.40 (d, J = 2.7 Hz, 1 H), 7.34 (dd, J = 9.3, 2.7 Hz, 1 H), 7.16 (d, J = 9.3 Hz, 1 H), 3.92 (s, 3H).13C {1H} NMR (126 MHz, CD3CN, 25 C, d): 165.4, 137.4, 136.2, 135.9, 135.7, 134.7, 131 .8, 131 .0, 1 19.4, 1 15.5, 1 15.0, 1 14.9, 104.5, 58.2.19F NMR (471 MHz, CD3CN, 25 C, d):-151 .5 (brs), -151.6 (brs).HRMS-ESI(m/z) calc’d for C20H14NOS2+[M]+, 348.051 1 ; found, 348.0508; deviation: 0.9 ppm.
Reference： [1]Patent: WO2020/94673,2020,A1 .Location in patent: Page/Page column 110
  • 53
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 39513-75-2 ]
  • [ 2362-50-7 ]
  • C22H17O2S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: tetrafluoroboric acid diethyl ether; 6-methyl-4-chromanone; thianthrene-5-oxide With trifluoroacetic anhydride In acetonitrile at 0 - 23℃; for 12h; Stage #2: sodium tetrafluoroborate In dichloromethane; water 6-Methyl-4-chromanone thianthrenium salt (18-TT) Under an ambient atmosphere, a 20-mL glass vial was charged with 6-methyl-4-chromanone (294 mg, 1.50 mmol, 1.00 equiv) and MeCN (3.0 mL, c = 0.50 M). After cooling to 0 °C, HBF4OEt2(0.26 mL, 0.31 g, 1.8 mmol, 1.2 equiv) and thianthrene-S-oxide (348 mg, 1.50 mmol, 1.00 equiv) was added to the vial while stirring the mixture, leading to a suspension. Subsequently, trifluoroacetic anhydride (0.63 mL, 0.95 g, 4.5 mmol, 3.0 equiv) was added in one portion at 0 °C, resulting in a color change to deep purple. Subsequently, the reaction mixture was allowed to reach 23 °C and stirred for 12 hours. The solution was diluted with DCM (5 mL) and poured onto a mixture of DCM (30 mL) and saturated aqueous NaHC03solution (20 mL). After stirring for 5 min at 23 °C, the mixture was poured into a separating funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (10% w/w, 4 x ca. 20 mL). The DCM layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (30:1 (v/v)), then the solvent was removed in vacuo to afford 18-TT (530 mg, 77% yield) as a light yellow solid.R/= 0.35 (DCM/MeOH, 15:1 , v/v). NMR Spectroscopy:1H NMR (500 MHz, CDCI3, 25 °C, d): 8.35 (dd, J = 7.9, 1.4 Hz, 2H), 7.84 (dd, J = 7.9, 1 .5 Hz, 2H), 7.80 (s, 2H), 7.73 (dd, J = 7.9, 1.5 Hz, 3H), 6.53 (d, J = 2.1 Hz, 1 H), 4.71 (t, J = 6.5 Hz, 2H), 2.75 (t, J = 6.5 Hz, 2H), 2.13 (s, 3H).13C {1H} NMR (126 MHz, CDCI3, 25 °C, d): 189.0, 157.9, 137.1 , 135.1 , 135.1 , 134.3, 133.0, 132.1 , 130.5, 130.2, 128.5, 127.7, 123.1 , 1 16.3, 109.4, 69.0, 37.2, 20.6.19F NMR (471 MHz, CDCI3, 25 °C, d):-151 .8 (brs), -151.9 (brs).HRMS-ESI(m/z) calc’d for C22H17S202+[M-BF4]+, 377.0665; found, 377.0664; deviation: 0.2 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 111; 112
  • 54
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 1459-55-8 ]
  • C29H29S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; 4-(1-adamantyl)toluene With trifluoroacetic anhydride In acetonitrile at 0 - 23℃; for 12h; Stage #2: sodium tetrafluoroborate In dichloromethane; water p-(1 -Adamantyl)toluene-derived thianthrenium salt (S7) Under an ambient atmosphere, a 20-ml glass vial was charged with p-(1 -adamantyl)toluene (339 mg, 1.50 mmol, 1 .00 equiv) and MeCN (3.0 ml, c = 0.50 M). After cooling to 0 °C, HBF4OEt2(0.25 ml_, 0.29 g, 1 .8 mmol, 1.2 equiv) and thianthrene-S-oxide (348 mg, 1.50 mmol, 1.00 equiv) was added to the vial while stirring the mixture, leading to a suspension. Subsequently, trifluoroacetic anhydride (0.63 ml_, 0.93 g, 4.5 mmol, 3.0 equiv) was added in one portion at 0 °C, resulting in a color change to deep purple. Subsequently, the reaction mixture was allowed to reach 23 °C and stirred for 12 h. The solution was diluted with DCM (5 ml.) and poured onto a mixture of DCM (30 ml.) and saturated aqueous NaHC03solution (20 ml_). After stirring for 5 min at 23 °C, the mixture was poured into a separating funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (10% w/w, 4 x ca. 20 ml_). The DCM layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (30:1 (v/v)), then the solvent was removed in vacuo to afford S7 (650 mg, 82%) as a colorless powder.R/ = 0.35 (DCM/MeOH, 15:1 , v/v).NMR Spectroscopy:1H NMR (500 MHz, CDCI3, 23 °C, d): 8.38 (d, J = 7.9 Hz, 2H), 7.86 (d, J = 7.9 Hz, 2H), 7.80 (t, J = 7.7 Hz, 2H), 7.69 (t, J = 7.6 Hz, 2H), 7.44 (d, J = 8.0 Hz, 1 H), 7.30 (d, J = 8.1 Hz, 1 H), 6.71 (s, 1 H), 2.63 (s, 3H), 1 .97 (s, 3H), 1 .69-1.67 (m, 3H), 1.60-1 .53 (m, 9H) ppm.13C NMR (125 MHz, CDCI3, 23 °C, d): 151.0, 137.2, 134.9, 134.8, 133.8, 130.9, 130.3, 130.2, 125.4, 120.7, 1 18.0, 77.4, 42.6, 36.3, 36.1 , 28.5, 19.8 ppm.19F NMR (471 MHz, CDCI3, 23 °C, d):-151.5 (brs), -151 .6 (brs) ppm.HRMS-ESI (m/z) calc’d for C29H29S2[M-BF4]+, 441 .17052; found, 441.17061 ; deviation: -0.2 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 120
  • 55
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 62809-67-0 ]
  • C32H28ClO4S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; fenofibrate With trifluoroacetic anhydride In acetonitrile at 0 - 23℃; for 2h; Stage #2: sodium tetrafluoroborate In dichloromethane; water Fenofibrate-derived thianthrenium salt (S9) Under an ambient atmosphere, a 20-ml glass vial was charged with fenofibrate (721 mg, 2.00 mmol, 1 .00 equiv) and MeCN (5.0 ml, c = 0.40 M). After cooling to 0 °C, HBF4OEt2(0.33 ml_, 0.39 g, 2.4 mmol, 1 .2 equiv) and thianthrene-S-oxide (464 mg, 2.00 mmol, 1 .00 equiv) was added to the vial while stirring the mixture, leading to a suspension. Subsequently, trifluoroacetic anhydride (0.84 ml_, 1 .3 g, 6.0 mmol, 3.0 equiv) was added in one portion at 0 °C, resulting in a color change to deep purple. Subsequently, the reaction mixture was allowed to reach 23 °C and stirred for 2 h. The solution was diluted with DCM (5 ml.) and poured onto a mixture of DCM (30 ml.) and aqueous K2C03solution (10% w/w, 10 ml_). After stirring for 5 min at 23 °C, the mixture was poured into a separating funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (10% w/w, 4 x ca. 20 mL). The DCM layer was dried over Na2S04, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (30:1 (v/v)), then the solvent was removed in vacuo to afford S9 (1.17 g, 88%) as a colorless powder.R/ = 0.35 (DCM/MeOH, 15:1 , v/v).NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 23 °C, d): 8.26 (dd, J = 7.9, 1 .4 Hz, 2H), 7.99 (dd, J = 8.8, 2.1 Hz, 1 H), 7.94 (dd, J = 8.5, 2.0 Hz, 2H), 7.84 (td, J = 7.7, 1.4 Hz, 2H), 7.78 (td, J = 7.7, 1 .4 Hz, 2H), 7.65-7.42 (m, 4H), 6.99 (d, J = 8.8 Hz, 1 H), 6.95 (d, J = 2.0 Hz, 1 H), 5.06-4.83 (m, 1 H), 1.74 (s, 6H), 1.03 (d, J = 6.2 Hz, 6H) ppm.13C NMR (126 MHz, CD3CN, 23 °C, d): 193.3, 172.4, 159.3, 140.0, 138.7, 138.2, 136.9, 136.7, 136.5, 133.9, 132.5, 132.2, 131 .7, 131.5, 130.3, 1 18.5, 1 1 1.2, 85.0, 71.6, 26.2, 22.2 ppm. one carbon missing because of overlap.19F NMR (471 MHz, CD3CN, 23 °C, d): -151 .7 (brs), -151 .8 (brs) ppm.HRMS-ESI(m/z) calc’d for C32H28CI104S2+[M-BF4]+, 575.1 1 120; found, 575.1 1205; deviation: - 1.5 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 121; 122
  • 56
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 6121-42-2 ]
  • C23H19O2S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; 1-Phenyl-cyclopropanecarboxylic acid methyl ester With trifluoroacetic anhydride In acetonitrile at 0 - 23℃; for 12h; Stage #2: sodium tetrafluoroborate In dichloromethane; water Methyl 1 -phenylcyclopropane-1-carboxylate-derived thianthrenium salt (S20) Under an ambient atmosphere, a 20-ml glass vial was charged with methyl 1 - phenylcyclopropane-1 -carboxylate (352 mg, 2.00 mmol, 1 .00 equiv) and MeCN (10 ml, c = 0.20 M). After cooling to 0 °C, HBF4-OEt2(0.33 ml_, 388 mg, 2.40 mmol, 1 .20 equiv) and thianthrene-S-oxide (464 mg, 2.00 mmol, 1.00 equiv) was added to the vial while stirring the mixture, leading to a suspension. Subsequently, trifluoroacetic anhydride (0.84 ml_, 1 .24 g, 6.00 mmol, 3.00 equiv) was added in one portion at 0 °C, resulting in a color change to deep purple. Subsequently, the reaction mixture was allowed to reach 23 °C and stirred for 12 h. The solution was diluted with DCM (5 ml.) and poured onto a mixture of DCM (30 ml.) and saturated aqueous NaHC03solution (20 ml_). After stirring for 5 min at 23 °C, the mixture was poured into a separating funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (10% w/w, 4 x ca. 20 ml_). The DCM layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (30:1 (v/v)), then the solvent was removed in vacuo to afford S20 (774 mg, 81 %) as a colorless powder.R/ = 0.50 (DCM/MeOH, 15:1 , v/v).NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 23 °C, d): 8.38 (dd, J = 7.9, 1 .4 Hz, 2H), 7.96 (dd, J = 7.9, 1 .5 Hz, 2H), 7.89 (td, J = 7.7, 1 .4 Hz, 2H), 7.82 (td, J = 7.7, 1.4 Hz, 2H), 7.55-7.42 (m, 2H), 7.19-7.04 (m, 2H), 3.52 (s, 3H), 1 .54 (q, J = 4.2 Hz, 2H), 1.14 (q, J = 4.2 Hz, 2H) ppm.13C NMR (125 MHz, CD3CN, 23 °C, d): 174.2, 146.4, 137.5, 136.1 , 136.0, 133.6, 131 .6, 130.9, 128.6, 123.2, 1 19.3, 52.9, 29.2, 17.1 ppm.19F NMR (471 MHz, CD3CN, 23 °C, d):-151.4 (brs), -151 .5 (brs) ppm.HRMS-ESI (m/z) calc’d for C23H1902S2[M-BF4]+, 391.08210; found, 391.08214; deviation: -0.1 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 129
  • 57
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  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • (S)-5-chloro-N-((2-oxo-3-phenyloxazolidin-5-yl)methyl)thiophene-2-carboxamide [ No CAS ]
  • C27H20ClN2O3S3(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; (S)-5-chloro-N-((2-oxo-3-phenyloxazolidin-5-yl)methyl)thiophene-2-carboxamide With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 18h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water Thianthrenium salt TT-15 Under ambient atmosphere, a 100 ml. Schlenk-tube equipped with a magnetic stir bar was charged with (S)-5-chloro-N-((2-oxo-3-phenyloxazolidin-5-yl)methyl)thiophene-2-carboxamide (800 mg, 2.38 mmol, 1 .00 equiv.), thianthrene S-oxide (569 mg, 2.45 mmol, 1.03 equiv.), and MeCN (15 ml_, c = 0.16 M). After cooling to -40 °C, trifluoroacetic anhydride (0.99 ml_, 1.5 g,7.1 mmol, 3.0 equiv.) was added while stirring. HBF4-OEt2(0.97 ml_, 1.2 g, 7.1 mmol, 3.0 equiv.) was added dropwise. The mixture was stirred at -40 °C for 1 h, then at ambient temperature for 17 h. The reaction mixture was concentrated under reduced pressure, and subsequently diluted with DCM (100 ml_). The solution was poured onto a saturated aqueous NaHC03solution (100 ml_), and the layers were separated. The organic phase was washed with aqueous NaBF4solution (2 x 100 ml_, 10%), and with water (100 ml_). The organic phase was dried over MgS0 , and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / MeOH (1 :0- 19:1 (v/v)) to afford 1 .25 g (83%) of TT-15 as white solid.R/ = 0.20 (DCM / MeOH, 95:5 (v/v)).NMR Spectroscopy:1H NMR (500 MHz, MeCN-d3, 25 °C, d): 8.34 - 8.32 (m, 2H), 7.96 - 7.94 (m, 2H),7.90 - 7.86 (m, 2H), 7.82 - 7.79 (m, 2H), 7.63 - 7.60 (m, 2H), 7.35 (d, J = 4.1 Hz,1 H), 7.33 - 7.31 (m, 1 H), 7.15 - 7.12 (m, 2H), 6.96 (d, J = 4.1 Hz, 1 H), 4.83 - 4.78 (m, 1 H), 4.05 (t, J = 9.1 Hz, 1 H), 3.80 (dd, J = 9.3, 6.1 Hz, 1 H), 3.71 - 3.59 (m, 2H). 13C NMR {1H} (126 MHz, MeCN-d3, 25 °C, d): 162.3, 155.1 , 144.0, 139.1 , 137.3, 136.1 , 135.8, 135.5, 131 .6, 130.9, 130.1 , 128.8, 128.7, 120.1 , 1 19.8, 1 17.3, 73.0,48.4, 42.9.19F NMR {1H} (471 MHz, MeCN-d3, 25 °C, d): -151 .5, -151.5.HRMS-ESI (m/z) calc’d. for C27H20CIN2O3S3+[M - BF4]+, 551 .031470; found, 551 .031913;deviation: +0.8 ppm.
83% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; (S)-5-chloro-N-((2-oxo-3-phenyloxazolidin-5-yl)methyl)thiophene-2-carboxamide With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 18h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 86; 87
[2]Berger, Florian; Berger, Georg; Engl, Pascal S.; Häring, Andreas P.; Pérez-Bitrián, Alberto; Ritter, Tobias [Journal of the American Chemical Society, 2019]
  • 58
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • methyl 2-(2-fluoro-4-biphenylyl)propionate [ No CAS ]
  • C28H22FO2S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; methyl 2-(2-fluoro-4-biphenylyl)propionate With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 15h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water Schlenk technique; Thianthrenium salt TT-25 Under ambient atmosphere, a 50 mL Schlenk-tube equipped with a magnetic stir bar was charged with flurbiprofen methyl ester (400 mg, 1 .55 mmol, 1.00 equiv.), thianthrene S-oxide (360 mg, 1.55 mmol, 1 .00 equiv.), and MeCN (7.7 mL, c = 0.20 M). After cooling to -40 °C, trifluoroacetic anhydride (0.65 mL, 0.98 g, 4.7 mmol, 3.0 equiv.) was added while stirring.HBF4OEt2(0.42 ml, 0.50 g, 3.1 mmol, 2.0 equiv.) was added dropwise. The mixture was stirred at -40 °C for 1 h, then at ambient temperature for 14 h. The reaction mixture was added to a saturated aqueous NaHC03solution (50 mL), and the aqueous phase was extracted with DCM (3 x 20 mL). The organic phase was washed with aqueous NaBF4solution (30 mL, 10%), dried over MgS0 , and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / MeOH (1 :0- 9: 1 (v/v)) to afford 746 mg (86%) of TT-25 as white solid.R/ = 0.35 (DCM / MeOH, 15:1 (v/v)).NMR Spectroscopy:1H NMR (500 MHz, DMSO-d6, 25 °C, d): 8.62 (dd, J = 7.9, 1.4 Hz, 2H), 8.09 (d, J = 7.1 Hz, 2H), 7.94 (td, J = 7.7, 1 .5 Hz, 2H), 7.88 (td, J = 7.7, 1.4 Hz, 2H), 7.72 (dd, J = 8.7, 1.6 Hz, 2H), 7.47 (t, J = 8.2 Hz, 1 H), 7.35 - 7.30 (m, 2H), 7.30 - 7.19 (m, 2H), 3.90 (q, J = 7.1 Hz, 1 H), 3.60 (s, 3H), 1 .41 (d, J = 7.2 Hz, 3H).13C NMR {1H} (126 MHz, DMSO-d6, 25 °C, d): 173.6, 158.8 (d, J = 247.4 Hz), 144.0 (d, J = 7.9 Hz), 139.0, 135.7, 135.4, 134.8, 130.9 (d, J = 3.1 Hz), 130.6 (d, J = 3.0 Hz), 130.3, 129.6, 128.4, 124.6 (d, J = 12.8 Hz), 124.3, 124.2 (d, J = 16.0 Hz), 1 19.1 , 1 15.4 (d, J = 23.0 Hz), 52.0, 43.8, 18.3.19F NMR {1H} (471 MHz, DMSO-d6, 25 °C, d): -1 17.8, -148.2, -148.3.HRMS-ESI (m/z) calc’d. for C28H22F02S2+[M - BF4]+, 473.103979; found, 473.103320; deviation: +1 .39 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 90; 91
  • 59
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 637-07-0 ]
  • C24H22ClO3S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; Clofibrate With trifluoroacetic anhydride In acetonitrile at 0 - 23℃; Stage #2: sodium tetrafluoroborate In dichloromethane; water Clofibrate ethyl ester-derived thianthrenium salt (S4) Under an ambient atmosphere, a 20-ml glass vial was charged with methyl gemfibrozil (1.21 g, 5.00 mmol, 1.00 equiv.) and MeCN (5.0 ml, c = 1.0 M). After cooling to 0 °C, HBF4OEt2(0.82 ml_, 0.97 g, 6.0 mmol, 1.2 equiv) and thianthrene-S-oxide (1.15 g, 5.00 mmol, 1.00 equiv) was added to the vial while stirring the mixture, leading to a suspension. Subsequently, trifluoroacetic anhydride (2.1 ml_, 3.2 g, 15 mmol, 3.0 equiv) was added in one portion at 0 °C, resulting in a color change to deep purple. Subsequently, the reaction mixture was allowed to reach 23 °C and stirred for 2 h. The solution was diluted with DCM (5 ml.) and poured onto a mixture of DCM (30 ml.) and saturated NaHC03solution. After stirring for 5 min at 23 °C, the mixture was poured into a separating funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (10% w/w, 4 x ca. 20 ml_). The DCM layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (30:1 (v/v)), then the solvent was removed in vacuo to afford S4 (2.38 g, 88%) as a white powder.R/= 0.35 (DCM/MeOH, 1/15, v/v). NMR Spectroscopy:1H NMR (500 MHz, DMSO-cfe, 23 °C, d) d 8.40 (dd, J = 7.8, 1.5 Hz, 2H), 8.10 (dd, J = 7.8, 1 .5 Hz, 2H), 7.89 (dtd, J = 23.2, 7.5, 1 .5 Hz, 4H), 7.68 (dd, J = 9.0, 2.6 Hz, 1 H), 6.92 (d, J = 9.0 Hz, 1 H), 6.64 (d, J = 2.6 Hz, 1 H), 4.10 (q, J = 7.1 Hz, 2H), 1.63 (s, 6H), 1.05 (t, J = 7.1 Hz, 3H) ppm.13C NMR (126 MHz, DMSO-cfe, 23 °C, d): 171.8, 152.9, 136.6, 136.3, 135.4, 135.1 , 131 .0, 130.0, 129.5, 125.8, 1 19.3, 1 18.3, 1 12.4, 82.5, 62.3, 25.2, 14.2 ppm.19F NMR (471 MHz, DMSO-cfe, 23 °C, d): -148.2 (brs), -148.3 (brs) ppm.HRMS-ESI (m/z) calculated for C24H2203S2CII+[M-BF4]+, 457.06934; found, 457.06917; deviation: 0.4 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 118; 119
  • 60
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 95737-68-1 ]
  • C32H26NO3S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; pyriproxyfen With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Sealed tube; Stage #2: sodium tetrafluoroborate In dichloromethane; water Pyriproxyfen derived thianthrenium salt 16b Under an ambient atmosphere, a 20 ml glass-vial was charged with pyriproxyfen (16) (642 mg, 2.00 mmol, 1.0 equiv.), and MeCN (8.0 ml, c = 0.25 M). HBF4OEt2(276 pi, 324 mg, 2 mmol,1.0 equiv.), and triflu oroacetic anhydride (834 pi, 1 .26 g, 6.00 mmol, 3.0 equiv.) were added while stirring the reaction mixture. After cooling to 0 °C, thianthrene-S-oxide S2 (464 mg,1 .00 mmol, 1 .0 equiv.) was added in one portion, followed by the addition of HBF4-OEt2(327 mI, 389 mg, 2.40 mmol, 1 .2 equiv.) in one portion at 0 °C, leading to a dark blue suspension. The vial was sealed with a screw-cap, and the mixture was stirred at 0 °C for 1 h, followed by stirring at 25 °C for 2 h until a slight purple solution was obtained. The reaction mixture wasconcentrated under reduced pressure, and subsequently, diluted with 5 ml DCM. The DCM phase was poured onto a saturated aqueous NaHC03solution (ca. 10 ml). The mixture was poured into a separatory funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (2 x ca. 10 ml, 5 % w/w), and with water (2 x ca. 10 ml). The DCM layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The product was dissolved in a minimal amount of DCM, and precipitated with Et20. The solid was dried in vacuo to afford 1.19 g (95 %) of 16b a colorless foam.NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 298 K, d): 8.30 (dd, J = 7.9 Hz, 1.2 Hz, 2H), 8.1 1 (ddd, J = 5.0 Hz, 2.0 Hz, 0.7 Hz, 1 H), 7.94 (dd, J = 7.9 Hz, 1.2 Hz, 2H), 7.86 (td, J = 7.7 Hz, 1.4 Hz, 2H), 7.78 (td, J = 7.8 Hz, 1 .3 Hz, 2H), 7.62 (ddd, J = 8.4 Hz, 7.1 Hz, 2.0 Hz, 1 H), 7.16 - 7.10 (m, 2H), 6.98 - 6.88 (m, 7H), 6.69 (dt, J = 8.4 Hz, 0.8 Hz, 1 H), 5.54 (m, 1 H), 4.15 {dd, J = 10.3 Hz, 6.0 Hz, 1 H), 4.09 (dd, J = 10.3 Hz, 4.1 Hz, 1 H), 1 .38 (d, J = 6.4 Hz, 3H).13C {1H} NMR (128 MHz, CDCI3, 298 K, d): 164.0, 163.8, 157.3, 148.7, 147.8, 140.1 , 137.1 ,135.9, 135.4, 131 .5, 130.9, 122.7, 120.0, 1 19.2, 1 17.9, 1 17.0, 1 16.0, 1 12.1 , 71 .8, 70.1 ,16.9.HRMS-ESI(m/z) calc’d for C32H26N03S2+[M-BF4]+, 536.134864; found, 536.13469; deviation: 0.32 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 78
  • 61
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 20017-67-8 ]
  • C27H23OS2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% Under ambient atmosphere, a 50 ml. round-bottom flask was charged with 3,3-diphenylpropan- 1 -ol (1.15 g, 5.40 mmol, 1 .00 equiv.), thianthrene-S-oxide (1.26 g, 5.40 mmol, 1 .00 equiv.) and dry MeCN (22 ml_, c = 0.25 M). After cooling to 0 C, trifluoroacetic anhydride (2.24 ml_, 3.44 g, 16.2 mmol, 3.00 equiv.) was added in one portion at 0 C, followed by HBF4OEt2(886 pl_,6.48 mmol, 1 .20 equiv.) addition at 0 C in one portion. The flask was sealed with a septum, which was equipped with a balloon. The mixture was allowed to stir at 0 C for 1 h, followed by warming the reaction mixture to 25 C over a period of 1 h. After stirring at 25 C for 1 h further, the reaction mixture was concentrated under reduced pressure, and diluted with 20 ml. CH2CI2. The CH2CI2solution was poured onto a saturated aqueous NaHC03solution (ca. 20 ml_). After stirring at 25 C for 2 h, the mixture was poured into a separatory funnel, and the layers were separated. The CH2CI2layer was collected, and the aqueous layer was further extracted with CH2CI2(2 x ca. 10 ml_). The combined CH2CI2solution was washed with aqueous NaBF4solution (2 x ca. 20 ml_, 5 % w/w). The CH2CI2layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2//-PrOH (50:1 to 30:1 , v/v). The product was collected and dried in vacuo to afford 26-TT (790 mg, 1 .54 mmol, 28 %) as a colorless foam.Rf= 0.28 (CH2CI2/MeOH, 15:1 , v/v).NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 298 K, d): 8.32 (d, J = 7.9 Hz, 2H), 7.94 (d, J = 7.9 Hz, 2H),7.87 (t, J = 7.7 Hz, 2H), 7.80 (t, J = 7.3 Hz, 2H), 7.41 (d, J = 8.7 Hz, 2H), 7.31-7.25 (m, 2H), 7.22 (d, J = 6.9 Hz, 2H), 7.18 (t, J = 7.1 Hz, 1 H), 7.05 (d, J = 8.8 Hz, 2H), 4.18 (t, J = 7.8 Hz, 1 H), 3.33 (t, J = 5.8 Hz, 2H), 2.24-2.15 (m, 3H) ppm.13C NMR (126 MHz, CD3CN, 298 K, d): 152.2, 144.4, 137.5, 136.1 , 135.9, 131.7, 131.0, 130.9, 129.7, 129.2, 128.7, 127.7, 122.1 , 1 19.52, 1 19.50, 60.1 , 47.6, 38.3 ppm.19F NMR (471 MHz, CD3CN, 298 K, d): -151 .73 (bs), -151 .79 (bs) ppm.HRMS-ESI (m/z) calculated for C27H230iS2+[M-BF4]+, 427.1 18485; found, 427.1 18620;deviation: -0.32 ppm.
Reference： [1]Patent: WO2020/94673,2020,A1 .Location in patent: Page/Page column 105
  • 62
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 131807-57-3 ]
  • C34H25N2O4S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; famoxadone With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 2h; Sealed tube; Stage #2: sodium tetrafluoroborate In dichloromethane; water Famoxadone derived thianthrenium salt 25a Under an ambient atmosphere, a 20 ml glass-vial was charged with famoxadone (25) (187 mg, 0.50 mmol, 1 .0 equiv.), and dry MeCN (2.0 ml, c = 0.25 M). Trifluoroacetic anhydride (0.21 ml, 0.32 g, 1.5 mmol, 3.0 equiv.) was added while stirring the reaction mixture. After cooling to 0 °C, thianthrene reagent (97 % (w/w) thianthrene-S-oxide S2, 3 % (w/w) thianthrene S1 , 1 16 mg, 0.50 mmol, 1.0 equiv.) was added in one portion, followed by the addition of HBF4-OEt2(82 pi, 97 mg, 0.60 mmol, 1 .2 equiv.) in one portion at 0 °C, leading to a purple suspension. The vial was sealed with a screw-cap, and the mixture was stirred at 0 °C for 1 h, followed by stirring at 25 °C for 1 h, until a slight purple solution was obtained. The reaction mixture was concentrated under reduced pressure, and diluted with 5 ml DCM. The DCM phase was poured onto a saturated aqueous NaHC03solution (ca. 10 ml). The mixture was poured into a separatory funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (2 x ca. 10 ml, 5 % w/w), and with water (2 x ca. 10 ml). The DCM layer was dried over Na2S0 , filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / /-PrOH, (30:1 (v/v)). The product was dissolved in 5 ml DCM, and precipitated with 20 ml Et20. The suspension was decanted, and the solid was dried in vacuo to afford 275 mg (81 %) of 25a as colorless solid.NMR Spectroscopy:1H NMR (600 MHz, CD3CN, 298 K, d): 8.23 (dddH^d, J = 8.0 Hz, 1 .3 Hz, 0.8 Hz, 0.4 Hz, 2H), 7.92 (dddH^d, J = 8.0 Hz, 2.1 Hz, 1 .3 Hz, 0.4 Hz, 2H), 7.84 (dd4^t, J = 8.0 Hz, 7.5 Hz, 1 .4 Hz, 2H), 7.76 (dddH^d, J = 7.9 Hz, 7.5 Hz, 1.3 Hz, 0.4 Hz, 2H), 7.51 - 7.49 (m, 2H), 7.48 (bs), 7.41 - 7.38 (m, 2H), 7.21 - 7.18 (m, 1 H), 7.06 (d, J = 9.1 Hz, 2H), 7.03 - 7.01 (m, 4H), 6.79 (d, J = 9.1 Hz, 2H), 1.96 (s, 3H).13C {1H} NMR (151 MHz, CD3CN, 298 K, d): 172.7, 159.5, 157.2, 153.1 , 150.3, 137.0, 135.8, 153.3, 131.6, 131 .4, 131.4, 131.1 , 130.9, 127.6, 125.2, 120.5, 120.2, 1 19.4, 1 14.9, 1 14.3, 86.2, 24.7.19F {1H} NMR (565 MHz, CD3CN, 298 K, d): -151 .4 (bs), -151.5 (bs).15N NMR (61 MHz, CD3CN, 298 K, d): -222.7, -293.0. (shifts taken from 2D spectrum). HRMS-ESI(m/z) calc’d for C34H25F4N204S2+[M-BF4]+, 589.125410; found, 589.125028; deviation: 0.6 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 20; 53; 54; 66
  • 63
  • [ 1628-89-3 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • C18H14NOS2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% A flame-dried, 100 ml. argon-filled Schlenk-tube equipped with a magnetic stir bar was charged with <strong>[1628-89-3]2-<strong>[1628-89-3]methoxypyridine</strong></strong> (525 pl_, 546 mg, 5.00 mmol, 1 .00 equiv.), thianthrene S-oxide (1.16 g, 4.99 mmol, 0.998 equiv.), and dry MeCN (20 ml_, c = 0.25 M). After cooling to -40 C, trifluoroacetic anhydride (2.09 ml_, 3.16 g, 15.0 mmol, 3.01 equiv.) was added while stirring. A solution of trimethylsilyl trifluoromethanesulfonate (1 .81 ml_, 2.22 g, 10.0 mmol, 2.00 equiv.) in 5 ml. of dry MeCN was added dropwise over 5 min. The mixture was stirred at -40 C for 1 h, then at ambient temperature for 18 h. The reaction mixture was concentrated under reduced pressure, and subsequently diluted with DCM (100 ml_). The solution was washed with aqueous NaBF4solution (3 x 100 ml_, 10%), and with water (100 ml_). The organic phase was dried over MgS0 , and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / MeOH (1 :0-20:1 (v/v)) to afford 1 .42 g (69%) of TT-7 as yellow foam.R/ = 0.18 (DCM / MeOH, 10:1 (v/v)).NMR Spectroscopy:1H NMR (500 MHz, CDCI3, 25 C, d): 8.53 (dd, J = 7.9, 1.1 Hz, 2H), 7.93 (d, J = 2.8 Hz, 1 H), 7.88 - 7.78 (m, 4H), 7.78 - 7.71 (m, 2H), 7.61 (dd, J = 9.1 , 2.8 Hz, 1 H), 6.79 (d, J = 9.1 Hz, 1 H), 3.88 (s, 3H).13C NMR {'H} (126 MHz, CDCI3, 25 C, d): 166.9, 147.6, 138.4, 136.4, 135.1 , 135.1 , 130.6, 130.4, 1 18.5, 133.9, 1 12.8, 54.7.19F NMR {1H} (471 MHz, CDCI3, 25 C, d): -150.0, -150.0.HRMS-ESI (m/z) calc?d. for CI8H14NOS2+[M - BF4]+, 324.051 134; found, 324.050980; deviation: +0.48 ppm
Reference： [1]Patent: WO2020/94673,2020,A1 .Location in patent: Page/Page column 85
[2]Journal of the American Chemical Society,2019
  • 64
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 80844-07-1 ]
  • C37H35O3S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: thianthrene-5-oxide; etofenprox With trifluoroacetic anhydride In acetonitrile at -78 - 25℃; Sealed tube; Stage #2: sodium tetrafluoroborate In dichloromethane; water Etofenprox derived thianthrenium salt 21 a Under an ambient atmosphere, a 20 ml glass-vial was charged with etofenprox (21 ) (188 mg, 0.50 mmol, 1 .0 equiv.), and dry MeCN (2.0 ml, c = 0.25 M). After cooling to -78 °C, trifluoroacetic anhydride (0.21 ml, 0.32 g, 1.5 mmol, 3.0 equiv.) was added to the frozen the reaction mixture. Thianthrene reagent (97 % (w/w) thianthrene-S-oxide (S2), 3 % (w/w) thianthrene (S1 ), 1 16 mg, 0.50 mmol, 1 .0 equiv.) was added in one portion at -78 °C. The vial was sealed with a screw-cap, and the mixture was allowed to stand at -78 °C for 1 h, followed by warming the reaction mixture to 25 °C over a period of 1 h. After stirring the deep purple reaction mixture at 25 °C for 1 h, the reaction mixture was concentrated under reduced pressure, and diluted with 5 ml DCM. The DCM phase was poured onto a saturated aqueous NaHC03solution (ca. 10 ml). The mixture was poured into a separatory funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (2cca. 10 ml, 5 % w/w), and with water (2 x ca. 10 ml). The DCM layer was dried over Na2S04, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / /-PrOH, (30:1 ). The product was dissolved in 5 ml DCM, and precipitated with 20 ml Et20. The suspension was decanted, and the solid was dried in vacuo to afford 279 mg (84 %) of 21 a as colorless solid.NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 298 K, d): 8.21 (dd, J = 7.9 Hz, 1.4 Hz, 2H), 7.85 (dd, J = 7.9 Hz, 1 .4 Hz, 2H), 7.80 (4%l, J = 7.7 Hz, 1.4 Hz, 2H), 7.72 (ddd, J = 7.9 Hz, 7.5 Hz, 1 .4 Hz, 2H), 7.58 (dd, J = 8.7 Hz, 2.3 Hz, 1 H), 7.38 - 7.34 (m, 2H), 7.30 (Y, J = 7.9 Hz, 1 H), 7.14 (tt, J = 7.7 Hz, 1.1 Hz, 1 H), 7.07 (d, J = 8.8 Hz, 1 H), 6.99 - 6.97 (m, 2H), 6.92 - 6.98 (m, 2H), 6.71 (Y, J = 1.8 Hz, 1 H), 6.58 (d, J = 2.3 Hz, 1 H), 4.26 (s, 2H), 4.17 (q, J = 7.0 Hz, 2H), 3.24 (s, 2H), 1.41 (t, J = 7.0 Hz, 3H), 1 .06 (s, 6H).13C {1H} NMR (126 MHz, CD3CN, 298 K, d): 158.2, 158.1 , 156.3, 142.1 , 141 .9, 138.1 , 136.1 , 135.7, 134.8, 131.2, 131.0, 130.8, 130.7, 128.0, 124.5, 123.1 , 1 19.8, 1 18.6, 1 18.19, 1 18.17, 1 15.0, 108.4, 79.9, 73.0, 67.1 , 39.4, 26.2, 14.8.19F {1H} NMR (471 MHz, CD3CN, 298 K, d): -151 .5 (bs), -151.6 (bs).HRMS-ESI(m/z) calc’d for C37H35F403S2+[M-BF4]+, 591.202600; found, 591.202215; deviation: 0.7 ppm
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 20; 49
  • 65
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 6385-02-0 ]
  • C26H18Cl2NO2S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Under an ambient atmosphere, a 20 ml glass-vial was charged with <strong>[6385-02-0]meclofenamic acid sodium salt</strong> (24) (159 mg, 0.50 mmol, 1 .0 equiv.), and dry MeCN (2.0 ml, c = 0.25 M). After cooling to - 78 C, trifluoroacetic anhydride (0.21 ml, 0.32 g, 1.5 mmol, 3.0 equiv.) was added to the frozen the reaction mixture. Thianthrene reagent (97 % (w/w) thianthrene-S-oxide (S2), 3 % (w/w) thianthrene (S1 ), 1 16 mg, 0.50 mmol, 1.0 equiv.) was added in one portion, followed by the addition of triflic acid (84 pi, 0.13 g, 1.1 mmol, 2.2 equiv.) in one portion at -78 C. The vial was sealed with a screw-cap, and the mixture was allowed to stand at -78 C for 1 h, followed by warming the reaction mixture to 25 C over a period of 1 h. Subsequently, the mixture was stirred for 1 h at 25 C. The reaction mixture was concentrated under reduced pressure, and diluted with 5 ml DCM. The DCM phase was poured onto a saturated aqueous NaHC03solution (ca. 10 ml). The mixture was poured into a separatory funnel and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (2 x ca. 10 ml, 5 % w/w), and with water (2cca. 10 ml). The DCM layer was dried over Na2S04, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / /- PrOH / HBF4OEt2(500:15:2 (v/v/v)). The product was dissolved in 5 ml DCM, and precipitated with 20 ml Et20. The solid was dried in vacuo to afford 270 mg (87 %) of 24a as colorless solid.NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 298 K, d): 9.96 (bs, 1 H), 9.79 (bs, 1 H), 8.21 (d, J = 8.0 Hz, 2H),7.95 - 7.88 (m, 3H), 7.84 (Y, J = 7.7 Hz, 2H), 7.76 (Y, J = 7.7 Hz, 2H), 7.39 (d, J = 8.3Hz, 1 H), 7.30 (d, J = 8.3 Hz, 1 H), 7.14 (dd, J = 9.3 Hz, 2.8 Hz, 1 H), 6.34 (d, J = 9.4 Hz, 1 H), 2.36 (s, 3H).13C { ' H} NMR (128 MHz, CD3CN, 298 K, d): 168.4, 152.7, 138.2, 136.7, 135.8, 135.3, 134.9, 134.0, 132.2, 131.6, 131 .5, 131 .0, 129.1 , 120.7, 1 16.8, 1 12.8, 109.4, 20.5.19F {1H} NMR (471 MHz, CD3CN, 298 K, d): -151 .6 (bs), -151.6 (bs).HRMS-ESI(m/z) calc?d for C26H18CI2F4N02S2+[M-BF4]+, 510.015680; found, 510.015055; deviation: 1 .2 ppm.
Reference： [1]Patent: WO2020/94673,2020,A1 .Location in patent: Page/Page column 20; 52; 53
  • 66
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 1601-18-9 ]
  • C32H25ClNO4S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: thianthrene-5-oxide; indomethacin methyl ester With trifluoroacetic anhydride In acetonitrile at 25℃; for 2h; Sealed tube; Cooling; Stage #2: sodium tetrafluoroborate In dichloromethane; water Indomethacin methylester derived thianthrenium salt 26a Under an ambient atmosphere, a 20 ml glass-vial was charged with indomethacin methylester (26) (186 mg, 0.50 mmol, 1.0 equiv.), and dry MeCN (2.0 ml, c = 0.25 M). After cooling to - 78 °C, trifluoroacetic anhydride (0.21 ml, 0.32 g, 1.5 mmol, 3.0 equiv.) was added to the frozen the reaction mixture. Thianthrene reagent (97 % (w/w) thianthrene-S-oxide (S2), 3 % (w/w) thianthrene (S1 ), 1 16 mg, 0.50 mmol, 1 .0 equiv.) was added in one portion at -78 °C. The vial was sealed with a screw-cap, and the mixture was allowed to stand at -78 °C for 1 h, followed by warming the reaction mixture to 25 °C. Subsequently, the mixture was stirred for 1 h at 25 °C. The reaction mixture was concentrated under reduced pressure, and diluted with 5 ml DCM. The DCM phase was poured onto a saturated aqueous NaHC03solution (ca. 10 ml). The mixture was poured into a separatory funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (2 x ca. 10 ml, 5 % w/w), and with water (2 x ca. 10 ml). The DCM layer was dried over Na2S04, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / /-PrOH, (30:1 (v/v)). The product was dissolved in 5 ml DCM, and precipitated with 20 ml Et20. The suspension was decanted, and the solid was dried in vacuo to afford 286 mg (85 %) of 26a as a colorless solid.NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 298 K, d): 8.16 (d4^t, J = 7.9 Hz, 0.9 Hz, 2H), 7.79 - 7.77 (m, 4H), 7.73 - 7.68 (m, 2H), 7.47 (s), 7.27 (s, 1 H), 6.16 (s, 1 H), 3.97 (s, 3H), 3.73 (s, 2H), 3.64 (s, 3H), 2.36 (s, 3H).13C {1H} NMR (128 MHz, CD3CN, 298 K, d): 171.8, 168.3, 154.4, 142.7, 140.5, 138.0,136.5, 135.9, 135.6, 133.6, 132.5, 131.3, 130.7, 130.5, 130.5, 1 18.2, 1 15.6, 113.8, 104.4,103.5, 58.0, 52.7, 29.9, 13.3.19F {1H} NMR (471 MHz, CD3CN, 298 K, d): -152.6 (bs), -152.7 (bs).HRMS-ESI(m/z) calc’d for C32H25CIF4N04S2+[M-BF4]+, 586.091180; found, 586.090807; deviation: 0.6 ppm.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - WO2020/94673, 2020, A1 Location in patent: Page/Page column 20; 54; 55
  • 67
  • [ 2362-50-7 ]
  • [ 358-23-6 ]
  • [ 71031-03-3 ]
  • C21H17OS2(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at -40 - 20℃; Inert atmosphere; Schlenk technique; 80 Example 80 Under a nitrogen atmosphere, a monosubstituted aromatic hydrocarbon substrate 8ae (0.2 mmol), thioanthracene-S-oxide (0.24 mmol) was added to a 25 mL Schlenk tube, and DCM (1.0 mL) was added, followed by stirring at -40°C.After slowly dropping Tf2O (0.24 mmol), it was stirred at -40°C for 30 minutes, followed by stirring at room temperature for 1 hour.Then, under a nitrogen atmosphere, sodium bicarbonate (0.6 mmol), arylboronic acid substrate 4k (0.3 mmol), bis(tri-tert-butylphosphine) palladium (0.01 mmol), acetone (1.0 mL) was added, and the cap was screwed tightly. At 50 , the reaction was stirred for 12 hours.After the reaction was completed, a small amount of DCM was added to quench the reaction, the celite was filtered, and the solvent was removed under reduced pressure. The crude product was separated and purified by a preparation plate (hexane/EtOAc (10/1)) to obtain 7ae (47.0 mg) as a white solid. 82%.
Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111187130, 2020, A Location in patent: Paragraph 0469-0471
  • 68
  • [ 67969-82-8 ]
  • [ 2362-50-7 ]
  • [ 103-45-7 ]
  • BF4(1-)*C22H19O2S2(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With trifluoroacetic anhydride In acetonitrile at 25℃; Sealed tube; Cooling;
With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; Sealed tube;
Reference： [1]Alvarez, Eva Maria; Berger, Florian; Plutschack, Matthew B.; Ritter, Tobias [Organic Letters, 2020]
[2]Alvarez, Eva Maria; Berger, Florian; Karl, Teresa; Ritter, Tobias; Torkowski, Luca [Angewandte Chemie - International Edition, 2021, vol. 60, # 24, p. 13609 - 13613][Angew. Chem., 2021, vol. 133, # 24, p. 13721 - 13725,5]
  • 69
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 77191-36-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; nefiracetam With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 6h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water
Reference： [1]Berger, Florian; Berger, Georg; Engl, Pascal S.; Häring, Andreas P.; Pérez-Bitrián, Alberto; Ritter, Tobias [Journal of the American Chemical Society, 2019]
  • 70
  • [ 67969-82-8 ]
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 606-45-1 ]
  • C21H17O3S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; 2-methoxybenzoic acid methyl ester With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water
Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; 2-methoxybenzoic acid methyl ester With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 6h; Stage #2: sodium tetrafluoroborate In water
Reference： [1]Berger, Florian; Berger, Georg; Engl, Pascal S.; Häring, Andreas P.; Pérez-Bitrián, Alberto; Ritter, Tobias [Journal of the American Chemical Society, 2019]
[2]Ye, Yun; Zhu, Jie; Huang, Yinhua [Organic Letters, 2021, vol. 23, # 6, p. 2386 - 2391]
  • 71
  • [ 553-03-7 ]
  • [ 2362-50-7 ]
  • [ 400620-72-6 ]
  • [ 92-85-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 1.5 h / -40 - 20 °C / Schlenk technique; Inert atmosphere 2: palladium diacetate; XPhos; sodium pivalate / acetone; dichloromethane / 21 h / 20 °C / Inert atmosphere
Reference： [1]Chen, Xiao-Yue; Huang, Yu-Hao; Zhou, Jian; Wang, Peng [Chinese Journal of Chemistry, 2020, vol. 38, # 11, p. 1269 - 1272]
  • 72
  • [ 13755-29-8 ]
  • [ 2362-50-7 ]
  • [ 34243-38-4 ]
  • [ 75-09-2 ]
  • C23H14NS4(1+)*BF4(1-)*CH2Cl2 [ No CAS ]
Reference： [1]Organic Letters,2020
  • 73
  • [ 2362-50-7 ]
  • [ 131807-57-3 ]
  • C34H25N2O4S2(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; Sealed tube;
Reference： [1]Alvarez, Eva Maria; Berger, Florian; Karl, Teresa; Ritter, Tobias; Torkowski, Luca [Angewandte Chemie - International Edition, 2021, vol. 60, # 24, p. 13609 - 13613][Angew. Chem., 2021, vol. 133, # 24, p. 13721 - 13725,5]
  • 74
  • [ 2362-50-7 ]
  • [ 1493-13-6 ]
  • [ 5786-21-0 ]
  • [ 92-85-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
43% With trifluoroacetic anhydride In acetonitrile at -78 - 25℃; for 3h; Sealed tube; A 20 ml glass-vial was charged with clozapine (0.20 mg, 0.61 mmol), and MeCN (5 ml).After cooling to -78 °C, trifluoroacetic anhydride (0.19 ml, 1.4 mmol) was added to the frozen thereaction mixture. Thianthrene (4 mg, 19 μmol), thianthrene-S-oxide (138 mg, 0.59 mmol) wereadded, followed by the addition of triflic acid (230 μl, 2.6 mmol, 4.2 equiv.) in one portion at -78 °C. The vial was sealed with a screw-cap, and the mixture was allowed to stand at -78 °C for1.5 hours, followed by warming the reaction mixture to 25 °C over a period of 1.5 hours. Thereaction mixture was concentrated under reduced pressure and dissolved in DCM (10 ml) followedby addition of saturated aqueous NaHCO3 solution (10 ml). The organic layers were separated,and the aqueous layer was extracted into DCM (2 x 10 mL). The DCM fractions were combined, dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The cruderesidue was purified by silica gel chromatography (0→100% MeOH/DCM) to provide 143 mg(43% yield) of S004 as a white solid.
Reference： [1]Boursier, Michelle E.; Hall, Mary P.; Hurst, Robin; Killoran, Michael P.; Kirkland, Thomas A.; Levin, Sergiy; Machleidt, Thomas; Ohana, Rachel Friedman; Zimmerman, Kristopher [Molecules, 2021, vol. 26, # 10]
  • 75
  • [ 2362-50-7 ]
  • [ 1493-13-6 ]
  • [ 3096-81-9 ]
  • [ 2926-30-9 ]
  • 5-(4-(4-cyanophenoxy)phenyl)-5H-thianthren-5-ium trifluoromethanesulfonate [ No CAS ]
Reference： [1]Organic Letters,2021,vol. 23,p. 4400 - 4405
  • 76
  • [ 2362-50-7 ]
  • [ 1493-13-6 ]
  • [ 620-88-2 ]
  • [ 2926-30-9 ]
  • 5-(4-(4-nitrophenoxy)phenyl)-5H-thianthren-5-ium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: thianthrene-5-oxide; trifluorormethanesulfonic acid; 4-nitrophenyl phenyl ether With trifluoroacetic anhydride In acetonitrile at -40 - 20℃; for 1h; Inert atmosphere; Stage #2: sodium triflate In water Inert atmosphere;
Reference： [1]Lin, Zeng-Hui; Tian, Ze-Yu; Zhang, Cheng-Pan [Organic Letters, 2021, vol. 23, # 11, p. 4400 - 4405]
  • 77
  • [ 2362-50-7 ]
  • [ CAS Unavailable ]
  • [ 77191-36-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic anhydride In acetonitrile at 0℃; for 1h; Sealed tube;
Reference： [1]Granatino, Paola; Lansbergen, Beatrice; Ritter, Tobias [Journal of the American Chemical Society, 2021, vol. 143, # 21, p. 7909 - 7914]
  • 78
  • [ 67969-82-8 ]
  • [ 2362-50-7 ]
  • [ 6969-90-0 ]
  • C21H18NO2S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 6h;
Reference： [1]Zhao, Yue; Yu, Congjun; Liang, Wenjing; Patureau, Frederic W. [Organic Letters, 2021, vol. 23, # 16, p. 6232 - 6236]
  • 79
  • [ 67969-82-8 ]
  • [ 2362-50-7 ]
  • [ 77191-36-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic anhydride In acetonitrile at 0℃; for 1h; Sealed tube;
Reference： [1]Granatino, Paola; Lansbergen, Beatrice; Ritter, Tobias [Journal of the American Chemical Society, 2021, vol. 143, # 27, p. 10477 - 10478]
  • 80
  • [ 2362-50-7 ]
  • [ 612-75-9 ]
  • C26H21S2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrafluoroboric acid diethyl ether complex; trifluoroacetic anhydride In acetonitrile at -40 - 20℃;
Reference： [1]Atodiresei, Iuliana L.; Liang, Wenjing; Patureau, Frederic W.; Yu, Congjun; Zhao, Yue [Chemical Communications, 2022, vol. 58, # 17, p. 2846 - 2849]
  • 81
  • [ 2362-50-7 ]
  • [ 321-60-8 ]
  • C24H16FS2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tetrafluoroboric acid diethyl ether complex; trifluoroacetic anhydride In acetonitrile at -40 - 20℃;
Reference： [1]Atodiresei, Iuliana L.; Liang, Wenjing; Patureau, Frederic W.; Yu, Congjun; Zhao, Yue [Chemical Communications, 2022, vol. 58, # 17, p. 2846 - 2849]
  • 82
  • [ 2362-50-7 ]
  • [ 164334-69-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
41% With tetrafluoroboric acid diethyl ether complex; trifluoroacetic anhydride In acetonitrile at -40 - 20℃;
Reference： [1]Zhao, Yue; Yu, Congjun; Liang, Wenjing; Atodiresei, Iuliana L.; Patureau, Frederic W. [Chemical Communications, 2022, vol. 58, # 17, p. 2846 - 2849]
  • 83
  • [ 132-65-0 ]
  • [ 2362-50-7 ]
  • C24H15S3(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With tetrafluoroboric acid diethyl ether complex; trifluoroacetic anhydride In acetonitrile at -40 - 20℃;
Reference： [1]Atodiresei, Iuliana L.; Liang, Wenjing; Patureau, Frederic W.; Yu, Congjun; Zhao, Yue [Chemical Communications, 2022, vol. 58, # 17, p. 2846 - 2849]
  • 84
  • [ 1484-12-4 ]
  • [ 2362-50-7 ]
  • C25H18NS2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With tetrafluoroboric acid diethyl ether complex; trifluoroacetic anhydride In acetonitrile at -40 - 20℃;
Reference： [1]Atodiresei, Iuliana L.; Liang, Wenjing; Patureau, Frederic W.; Yu, Congjun; Zhao, Yue [Chemical Communications, 2022, vol. 58, # 17, p. 2846 - 2849]
  • 85
  • [ 2362-50-7 ]
  • [ 1150-62-5 ]
  • C30H20NS2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tetrafluoroboric acid diethyl ether complex; trifluoroacetic anhydride In acetonitrile at -40 - 20℃;
Reference： [1]Atodiresei, Iuliana L.; Liang, Wenjing; Patureau, Frederic W.; Yu, Congjun; Zhao, Yue [Chemical Communications, 2022, vol. 58, # 17, p. 2846 - 2849]

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