Alternatived Products of [ 21856-94-0 ]
Product Details of [ 21856-94-0 ]
| CAS No. : | 21856-94-0 |
MDL No. : | N/A |
| Formula : |
C14H14Se2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
340.18
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 21856-94-0 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 21856-94-0 ]
* 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 [ 21856-94-0 ]
- 1
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[ 2731-73-9 ]
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[ 21856-94-0 ]
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Se-(4-methylphenyl)-L-selenocysteine
[ No CAS ]
- 2
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[ 21856-94-0 ]
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[ 2731-73-9 ]
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Se-(4-methylphenyl)-D-selenocysteine
[ No CAS ]
- 3
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[ 13054-02-9 ]
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[ 64-17-5 ]
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[ 21856-94-0 ]
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6-<i>p</i>-tolylselanyl-nicotinic acid ethyl ester
[ No CAS ]
- 4
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[ 21856-94-0 ]
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[ 4044-58-0 ]
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8-bromo-1-(p-tolylselanyl)naphthalene
[ No CAS ]
- 5
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[ 21856-94-0 ]
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[ 20816-79-9 ]
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8-chloro-1-(p-tolylselanyl)naphthalene
[ No CAS ]
- 6
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[ 21856-94-0 ]
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[ 126496-79-5 ]
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(R)-methyl 2-(tert-butoxycarbonylamino)-3-(p-tolylselanyl)propanoate
[ No CAS ]
- 7
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[ 21856-94-0 ]
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[ 932-87-6 ]
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[ 51094-36-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 86% |
With 1H-imidazole; magnesium In N,N-dimethyl-formamide at 120℃; for 48h; |
|
| 83% |
With Cu/Al<SUB>2</SUB>O<SUB>3</SUB>; zinc In tetrahydrofuran at 70℃; for 8h; Inert atmosphere; |
4.2 General experimental procedure for the synthesis of alkynyl selenides. Representative procedure for phenyl(phenylethynyl)selane (Table 2, entry 2)
General procedure: To a solution of 1-(2-bromoethynyl)benzene (181 mg, 1 mmol) and diphenyl diselenide (156 mg, 0.5 mmol) in THF (4 mL), Cu/ Al2O3 (70 mg) and zinc powder (32.5 mg, 0.5 mmol) were added and the mixture was stirred under argon at 70 °C for 8 h (TLC). After being allowed to cool, the THF was evaporated and the reaction mixture was extracted with ethyl acetate (3×10 mL). The extract was washed with water and brine and dried over Na2SO4. The crude product was purified by column chromatography over silica gel (hexane) to afford pure phenyl (2-phenylethynyl)selane as a yellow liquid (236 mg, 92%). |
Reference：
[1]Sharma, Anuj; Schwab, Ricardo S.; Braga, Antonio L.; Barcellos, Thiago; Paixão, Marcio W.
[Tetrahedron Letters, 2008, vol. 49, # 35, p. 5172 - 5174]
[2]Ahammed, Sabir; Bhadra, Sukalyan; Kundu, Debasish; Ranu, Brindaban C.; Sreedhar, Bojja
[Tetrahedron, 2012, vol. 68, # 51, p. 10542 - 10549,8]
Ahammed, Sabir; Bhadra, Sukalyan; Kundu, Debasish; Sreedhar, Bojja; Ranu, Brindaban C.
[Tetrahedron, 2012, vol. 68, # 51, p. 10542 - 10549]
- 8
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[ 73058-30-7 ]
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[ 21856-94-0 ]
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[ 1159428-83-7 ]
- 9
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[ 21856-94-0 ]
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[ 5720-07-0 ]
-
[ 90158-88-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 96% |
With Oxone In ethanol at 60℃; for 4h; Schlenk technique; |
General Procedure for the Oxone mediated Synthesis of Diorganoyl Selenides and Tellurides(3)
General procedure: To a Schlenk tube equipped with a small magnetic stirring bar were added the appropriatediorganoyl dichalcogenide (0.15 mmol), the appropriate aryl boronic acid (0.3 mmol), Oxone(0.3 mmol) and dry EtOH (0.5 mL). The resulting mixture was stirred at 60 °C until the totalconsumption of the starting materials. After that, the reaction mixture was cooled to roomtemperature, and was quenched using water (5 mL). The mixture was then extracted using ethylacetate (10 mL) and washed with water (3 x 10 mL). The combined organic layers were driedover anhydrous MgSO4 and concentrated under vacuum to yield the crude product, which waspurified by flash chromatography on silica gel using hexane or a mixture of hexane/ethyl acetateas eluent. |
| 92% |
With MCM-41 immobilized bipyridine copper(I) complex In water; dimethyl sulfoxide at 110℃; for 14h; Schlenk technique; Green chemistry; |
|
| 87% |
With copper(II) oxide In dimethyl sulfoxide at 100℃; for 24h; Air atmosphere; |
|
| 80% |
With copper(l) iodide; dimethyl sulfoxide In glycerol at 110℃; for 30h; |
|
| 75% |
With tetrabutylammonium tetrafluoroborate In acetonitrile at 50℃; for 3h; Electrolysis; Green chemistry; |
|
| 72% |
With silver nitrate In 1,4-dioxane at 100℃; for 6h; |
|
Reference：
[1]Perin, Gelson; Duarte, Luis Fernando B.; Neto, José S. S.; Silva, Márcio S.; Alves, Diego
[Synlett, 2018, vol. 29, # 11, p. 1479 - 1484]
[2]Zhao, Hong; Jiang, Yuanyuan; Chen, Qiurong; Cai, Mingzhong
[New Journal of Chemistry, 2015, vol. 39, # 3, p. 2106 - 2115]
[3]Location in patent: scheme or table
Alves, Diego; Santos, Cayane G.; Paixão, Márcio W.; Soares, Letiére C.; Souza, Diego de; Rodrigues, Oscar E.D.; Braga, Antônio L.
[Tetrahedron Letters, 2009, vol. 50, # 48, p. 6635 - 6638]
[4]Ricordi, Vanessa G.; Freitas, Camilo S.; Perin, Gelson; Lenardao, Eder J.; Jacob, Raquel G.; Savegnago, Lucielli; Alves, Diego
[Green Chemistry, 2012, vol. 14, # 4, p. 1030 - 1034]
[5]Cai, Hu; Fu, Zhengjiang; Guo, Shengmei; He, Dongdong; Yi, Xuezheng; Yin, Jian
[Green Chemistry, 2022, vol. 24, # 1, p. 130 - 135]
[6]Goldani, Bruna; Ricordi, Vanessa G.; Seus, Natália; Lenardão, Eder J.; Schumacher, Ricardo F.; Alves, Diego
[Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 11472 - 11476]
- 10
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[ 4472-44-0 ]
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[ 21856-94-0 ]
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[ 1429406-43-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 78% |
|
General procedure: To a solution of diaryldiselenide, Ar2Se2 (Ar = phenyl, naphthyl, tolyl, 4-chloro-2-pyrimidyl) in 50 ml of C2H5OH-DMF (3:2) was added 0.456 g (12 mmol) of sodium borohydride in parts with continuous stirring at 0?5 °C. To the resulting solution, 10 mmol of 4,6-dimethyl-2-chloropyrimidine diluted with an equal volume of DMF was added drop wise. Reaction was complete within 1?2 h. Extraction was done in dichloromethane after removing ethanol under vacuum. The organic layer was repeatedly washed with distilled water (3 × 40 ml), dried over anhydrous sodium sulfate. Solvent was removed on a rota evaporator and the product was subjected to purification on a silica column using hexane as eluant. |
- 11
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[ 21856-94-0 ]
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[ 761-65-9 ]
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Se-p-tolyl N,N-dibutylselenocarbamate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 50% |
With tert.-butylhydroperoxide; water at 120℃; for 12h; Molecular sieve; Inert atmosphere; |
|
- 12
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[ 2700-30-3 ]
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[ 21856-94-0 ]
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Se-p-tolyl N,N-diisopropylselenocarbamate
[ No CAS ]
- 13
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[ 21856-94-0 ]
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[ 1207749-70-9 ]
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(6-dimethylamino-3-pyridyl)4-methylphenyl selenide
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 80% |
With MCM-41 immobilized bipyridine copper(I) complex In water; dimethyl sulfoxide at 110℃; for 14h; Schlenk technique; Green chemistry; |
|
- 14
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[ 1048-08-4 ]
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[ 21856-94-0 ]
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[ 83859-32-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 7 %Chromat. |
With 1,10-Phenanthroline; copper (I) acetate In dimethyl sulfoxide at 100℃; for 24h; |
|
Reference：
[1]Matsumura, Mio; Shibata, Kohki; Ozeki, Sota; Yamada, Mizuki; Murata, Yuki; Kakusawa, Naoki; Yasuike, Shuji
[Synthesis, 2016, vol. 48, # 5, p. 730 - 736]
- 15
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[ 21856-94-0 ]
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[ 1048-05-1 ]
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[ 83859-32-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 10 %Chromat. |
With 1,10-Phenanthroline; copper (I) acetate In dimethyl sulfoxide at 100℃; for 24h; |
|
Reference：
[1]Matsumura, Mio; Shibata, Kohki; Ozeki, Sota; Yamada, Mizuki; Murata, Yuki; Kakusawa, Naoki; Yasuike, Shuji
[Synthesis, 2016, vol. 48, # 5, p. 730 - 736]
- 16
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[ 21856-94-0 ]
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[ 2216-69-5 ]
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(1-methoxynaphthalen-4-yl)(p-tolyl)selane
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 87% |
With silver hexafluoroantimonate; Cu(OAc)2*H2O In 1,2-dichloro-ethane at 100℃; for 12h; Inert atmosphere; regioselective reaction; |
|
| 80% |
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 0.166667h; |
11 Example 11
4mL reaction flasks were added1-methoxynaphthalene (0.2mmol),1,2-Di-p-methylphenyl diselenide (0.4 mmol), PIFA (0.2 mmol) and DCM (2.0 mL),Stir at room temperature. The detection reaction was followed by TLC.After 10 minutes, the reaction was complete. Water and dichloromethane were added to the reaction system, and the organic layer was separated.The aqueous layer was washed twice with dichloromethane,All organic layers were combined and washed twice with water.The organic layer was dried over anhydrous sodium sulfate, concentrated,Column chromatography (100% petroleum ether),The product 52.4 mg was obtained with a yield of 80%, |
- 17
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[ 18908-66-2 ]
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[ 21856-94-0 ]
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(2-ethylhexyl) p-tolyl selenide
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 87% |
With zinc In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere; |
18 General procedure for the heterogeneous ruthenium-catalyzed reaction of diaryl diselenides with alkyl halides
General procedure: Under argon atmosphere, to a mixture of diaryl diselenide (0.5mmol), zinc (52mg, 0.8mmol), and MCM-41-2N-RuCl3 (2mol%) were successively added DMF (3mL) and alky halide (1.2mmol). The mixture was stirred at 100°C for 2h. The reaction mixture was cooled to room temperature and diluted with EtOAc (20mL) and filtered. The MCM-41-2N-RuCl3 catalyst was washed with diluted hydrochloric acid (2×5mL), distilled water (2×5mL), and EtOH (2×5mL) and reused in the next run. The filtrate was washed with brine (2×10mL), dried over MgSO4. After removal of the solvent under reduced pressure, the residue was purified by silica gel chromatography using light petroleum ether or light petroleum ether/ CH2Cl2 (ca. 10:1, v/v) as the eluent to afford the desired product 3. |
- 18
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[ 21856-94-0 ]
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[ 103-63-9 ]
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[ 134480-08-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 92% |
With zinc In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere; |
19 General procedure for the heterogeneous ruthenium-catalyzed reaction of diaryl diselenides with alkyl halides
General procedure: Under argon atmosphere, to a mixture of diaryl diselenide (0.5mmol), zinc (52mg, 0.8mmol), and MCM-41-2N-RuCl3 (2mol%) were successively added DMF (3mL) and alky halide (1.2mmol). The mixture was stirred at 100°C for 2h. The reaction mixture was cooled to room temperature and diluted with EtOAc (20mL) and filtered. The MCM-41-2N-RuCl3 catalyst was washed with diluted hydrochloric acid (2×5mL), distilled water (2×5mL), and EtOH (2×5mL) and reused in the next run. The filtrate was washed with brine (2×10mL), dried over MgSO4. After removal of the solvent under reduced pressure, the residue was purified by silica gel chromatography using light petroleum ether or light petroleum ether/ CH2Cl2 (ca. 10:1, v/v) as the eluent to afford the desired product 3. |
- 19
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[ 21856-94-0 ]
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[ 1137-41-3 ]
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phenyl(4-(p-tolylselanyl)phenyl)methanone
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 79% |
With tert.-butylnitrite; iron In dimethyl sulfoxide at 30℃; for 8h; Inert atmosphere; |
Representative experimental procedure for the reaction of p-anisidine and diphenyl diselenide for the synthesis of (4-Methoxyphenyl)(phenyl)selane (Scheme 3, 3d):
General procedure: A mixture of p-anisidine (1.0 mmol, 123 mg), t BuONO (1.1 mmol, 113.3 mg), diphenyl diselenide (0.5 mmol, 156 mg), freshly prepared Fe(0) catalyst (1 mmol) and DMSO (3 mL) was stirred under room temperature (30 °C) for 8 hours (TLC) under argon atmosphere and the product was extracted by ethyl acetate. The extract was washed with water (20 mL) and brine (20 mL). Then the organic phase was dried over Na2SO4 and evaporated to leave the crude product which was purified by column chromatography over silica gel (hexane/ethyl acetate 98:2) to provide the pure (4-methoxyphenyl)(phenyl)selane 3 as a gummy liquid (215 mg, 82%). |
- 20
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[ 491-38-3 ]
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[ 21856-94-0 ]
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3-(4-tolylselanyl)-4H-chromen-4-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 78% |
With oxone||potassium monopersulfate triple salt In N,N-dimethyl-formamide for 0.6h; Sonication; Green chemistry; regioselective reaction; |
2. General procedure for synthesis of 3-(phenylselanyl)-4H-chromen-4-ones 3
General procedure: To a 10 mL round-bottomed glass vial, the chromone 1 (0.250 mmol), diselenide 2a-h (0.125 mmol), Oxone (0.077 g; 0.250 mmol) and DMF (2.0 mL) were added. The US probe was placed in the reaction vial, which was sonicated (20 KHz, 60% of sonic amplitude) for the time indicated in Table 2. The reaction progress was monitored by TLC in order to evaluate the starting materials consumption. After that, the reaction mixture was extracted with ethyl acetate (3x 15.0 mL), the organic phase was separated, dried over MgSO4 and the solvent was evaporated under reduced pressure. The product was isolated by column chromatography using silica gel 60A (0.060-0.200 mm-Across) and using a mixture of hexane and ethyl acetate (90:10). |
| 64% |
With ammonium iodide In N,N-dimethyl-formamide at 135℃; for 12h; regioselective reaction; |
2 General procedure for the synthesis of 3-selenyl-chromones 5
General procedure: 0.5 mL DMF was added into the flask charged with 0.25 mmol of flavones, 0.25 mmol of diaryl diselenides, NH4I (1.25 mmol). The mixture was stirred at 135 °C for 12 hours, then cooled down to room temperature, diluted with 20 mL ethyl acetate and washed with 10 mL H2O. The aqueous layer was extracted twice with ethyl acetate (5 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents the residue was purified by flash column chromatography (silica gel, PE/EtOAc=10:1) to afford the desired products 5. |
Reference：
[1]Araujo, Daniela R.; Lima, Yanka R.; Barcellos, Angelita M.; Jacob, Raquel G.; Silva, Márcio S.; Perin, Gelson
[Arkivoc, 2020, vol. 2020, # 6, p. 276 - 286]
[2]Guo, Tao
[Synthetic Communications, 2017, vol. 47, # 22, p. 2053 - 2061]
- 21
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[ 21856-94-0 ]
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[ 4105-21-9 ]
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3-[(4-methylphenyl)selanyl]-2-phenylimidazo[1,2-a]pyridine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 87% |
With ammonium iodide In acetonitrile at 20℃; for 18h; |
General procedure for visible light promoted synthesis of 3-selanylimidazo[1,2-a]pyridines (3-13)
NH4I (0.1 mmol) was added to a solution of imidazo[1,2-a]pyridine (1a, 0.5 mmol) and diaryl diselenide(0.25 mmol) in MeCN (3 mL), and the reaction mixture was stirred under blue LED (5 W) irradiation for18 h under ambient air. The progress of the reaction was monitored by TLC. After completion of thereaction, EtOAc (10 mL) and water (10 mL) were added and the reaction mixture was extracted withEtOAc (10 mL x 2). The combined organic layers were washed water (10 mL) and brine (20 mL). Theorganic phase was dried over anhydrous MgSO4 and concentrated under vacuum to get the crude residue.The residue was purified by column chromatograph on silica gel (Hexane-EtOAc = 4:1-1:4) to afforded3-13 (66-93%). Known products (3-9, 11, 13) were confirmed by comparison of mp, NMR data, and MSspectra with that in literature (See Supporting Information). |
| 69% |
With ammonium iodide; water; acetic acid; dimethyl sulfoxide at 110℃; for 14h; Green chemistry; regioselective reaction; |
25 4.2.1. General procedure for synthesis
General procedure: N-heteroarene (0.25 mmol), diorganyl dichalcogenide (0.125 mmol) NH4I (0.025 mmol, 10 mol%, 3.6 mg), acetic acid (1 eq.) and the mixture of DMSO/H2O (2.5:2.5 eq.) were placed into a round-bottom flask. The reaction was stirred at 110 °C in an oil bath for appropriate time (Tables 3-6). After the completion of the reaction, the mixture was cooled to room temperature, quenched with water and the aqueous layer was extracted with EtOAc. The organic phase was dried over MgSO4, filtered, and the volatiles were completely removed under vacuum to give the crude product. Purification by flash chromatography on silica with a mixture of Hexane/EtOAc as eluent furnished the desired chalcogenated product. |
| 0.098 g |
With copper(II) sulfate; potassium iodide for 2h; Sonication; |
General procedure for the synthesis of 3-selanylimidazo[1,2-a]pyridines 5a-q.
General procedure: A mixture of 2-aminopyridine 1 (0.5 mmol), 2-bromoacetophenone derivative 2 (0.5 mmol), K2CO3 (0.103g, 0,75 mmol) and PEG-400 (1 mL), was added to a 10 mL vial. Then, the ultrasonic probe was introduced in the flask and the mixture was sonicated at 20 kHz and 60% of amplitude. The progress of the reaction was monitored by TLC as indicated in Table 2. Then diorganyldiselenide 4 (0.3 mmol) and CuSO4/KI (2 equiv.) were added and the reaction mixture was sonicated again at 20 kHz and 60% of amplitude by the time indicated in Table 4. The progress of the reaction was monitored by TLC. After that, the reaction mixture was received in water (10 mL), extracted with ethyl acetate (3 x 5 mL), dried over MgSO4 and concentrated under vacuum. The residue was purified by column chromatography using silica gel and a mixture of ethyl acetate/hexanes as the eluent. |
Reference：
[1]Murata, Yuki; Kanasaki, Keiko; Kondo, Kaito; Kakusawa, Naoki; Matsumura, Mio; Yasuike, Shuji
[Heterocycles, 2019, vol. 99, # 1, p. 596 - 603]
[2]Bettanin, Luana; Saba, Sumbal; Doerner, Carlos V.; Franco, Marcelo S.; Godoi, Marcelo; Rafique, Jamal; Braga, Antonio L.
[Tetrahedron, 2018, vol. 74, # 29, p. 3971 - 3980]
[3]Vieira, Beatriz M.; Padilha, Nathalia; Nascimento, Nelson M.; Perin, Gelson; Alves, Diego; Schumacher, Ricardo F.; Lenardão, Eder J.
[Arkivoc, 2019, vol. 2019, # 2, p. 6 - 23]
- 22
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[ 21856-94-0 ]
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[ 406207-65-6 ]
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2-tert-butyl-3-(4-methylphenylseleno)imidazo[1,2-a]pyridine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 78% |
With copper(II) ferrite; oxygen; In tetrahydrofuran; at 60℃; for 16h;Schlenk technique; |
At room temperature, A 25 ml Schlenk tube containing a magnetic stir bar was charged with copper ferrite (0.03 mmol). 2-tert-Butyl imidazolium [1,2-a] pyridine (0.2 mmol), p-methyldiphenyl diselenide (0.15 mmol), 2 mL anhydrous THF was added under oxygen, and the tube was placed in an oil bath Stir in the pot and react at 60 C for 16 h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature. The magnet was placed outside the reaction vessel, and the catalyst was adsorbed on the wall of the reaction vessel by magnetic attraction. The reaction solution was poured into a separatory funnel, and 5 ml of ethyl acetate was poured into the reaction vessel, and the catalyst was washed twice. The ethyl acetate was poured into a separatory funnel, and 5 ml of water and 5 ml of ethyl acetate were added to the separatory funnel, and the reaction mixture was extracted, and the extraction was repeated 4 times. The organic phases were combined and dried over 2 g of anhydrous sodium sulfate. The organic phase was freed of solvent by rotary evaporator. The residue was purified on a silica gel column (silica gel size 200 to 300 mesh, eluent petroleum ether / ethyl acetate (5:1, v/v)) The target product 2-tert-butyl-3-(4-methylphenylseleno)imidazo[1,2-a]pyridine was obtained in a yield of 78%. |
- 23
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[ 63224-42-0 ]
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[ 21856-94-0 ]
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4,7-bis(p-tolylselanyl)benzo[c][1,2,5]selenodiazole
[ No CAS ]
- 24
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[ 21856-94-0 ]
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[ 35944-64-0 ]
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(3-iodo-4-methylphenyl)(p-tolyl)selane
[ No CAS ]
- 25
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[ 21856-94-0 ]
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[ 66-22-8 ]
-
5-(p-tolylselanyl)pyrimidine-2,4(1H,3H)-dione
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 96% |
With dihydrogen peroxide; sodium iodide In dimethyl sulfoxide at 50℃; for 3h; Schlenk technique; |
17 Example 17
Add 0.2 mmol of uracil to a clean Schlenk reaction tube.0.1 mmol NaI and 0.3 mmol p-methyldiphenyl diselenide and a stir bar, then add 3 mL of DMSO solvent with a syringe.Finally, add 0.6mmol with a micro syringe.H2O2, reaction at 50 ° C for 3 hours, TLC dot plate detection; after the reaction is over,The reaction solution was added with water and extracted with ethyl acetate three times.The organic layer is concentrated and separated by column chromatography to obtain pure5-p-tolylselenouracil, white solid,The yield was 96% |
| 93% |
With ammonium iodide In N,N-dimethyl-formamide at 50℃; for 2h; Electrochemical reaction; Green chemistry; |
|
| 91% |
With potassium iodide In dimethyl sulfoxide at 20℃; for 13h; Electrolysis; Green chemistry; |
2.1 General experimental procedures for Compound 3
General procedure: In an undivided three-necked flask (25 mL) equipped with a stir bar, uracils (0.5 mmol), various dialkyldiselenides (diaryldiselenides) (0.25 mmol), KI (0.125 mmol) and DMSO (8 mL) were added. The flask was equipped with platinum electrodes (15 mm x 15 mm x 0.3 mm) as cathode, graphite rod (Φ 6 mm) as the anode. The reaction mixture was stirred and electrolyzed at a constant current of 10 mA under room temperature for 15 h. Method A: The reaction mixture was diluted with water, and the products were extracted with ethyl acetate (3 × 40 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The pure products 3 were obtained by flash chromatography on silica gel by using dichloromethane/ethyl acetate as elute. Method B: After completion, water (10 mL) was added dropwise into the mixture. The precipitates were formed and collected by filtration and wash with ethyl acetate to give the pure products 3. |
| 90% |
With dihydrogen peroxide; sodium iodide In dimethyl sulfoxide at 50℃; |
|
Reference：
[1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Institute of Chemistry (in: CAS) - CN109651267, 2019, A
Location in patent: Paragraph 0141-0146
[2]Chen, Yan-Yan; Jiang, Cai-Na; Ma, Xian-Li; Wang, Qian; Xu, Yan-Li
[European Journal of Organic Chemistry, 2020]
[3]Chen, Jin-Yang; Zhong, Chun-Tao; Gui, Qing-Wen; Zhou, Yuan-Ming; Fang, Yang-Yang; Liu, Kai-Jian; Lin, Ying-Wu; Cao, Zhong; He, Wei-Min
[Chinese Chemical Letters, 2021, vol. 32, # 1, p. 475 - 479]
[4]Li, Xue-Dong; Gao, Yu-Ting; Sun, Ying-Jie; Jin, Xiao-Yang; Wang, Dong; Liu, Li; Cheng, Liang
[Organic Letters, 2019, vol. 21, # 17, p. 6643 - 6647]
- 26
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[ 5720-05-8 ]
-
[ 21856-94-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 89% |
With selenium(IV) oxide; iodine In 2-methyltetrahydrofuran at 60℃; for 2h; Green chemistry; |
General experimental procedure for the synthesis of diaryl diselenides
General procedure: The reaction was carried out in a 25 mL round bottom flask equipped with magnetic stirbar charged with phenyl boronic acid (1.0 equiv), selenium dioxide (1.0 equiv), I2 (1.0 equiv), and 2-Me-THF (0.8 mL). The resulting reaction mixture was stirred at 60 oC temperature for 2-4 h. The reaction progress was monitored by TLC. After completion of the reaction, iodine quenched with hypo solution and it was worked up with ethyl acetate (3 × 10 ml) and saturated brine solution. Crude product was purified by column chromatography. The identity and purity of the product was confirmed by 1H NMR, 13C NMR, and EI-MS. |
|
With selenium; silver nitrate In dimethyl sulfoxide at 120℃; for 2h; |
|
|
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 14 h / 60 °C / Green chemistry
2: potassium hydroxide / dimethyl sulfoxide / 12 h / 110 °C / Green chemistry |
|
|
Stage #1: 4-methylphenylboronic acid With selenium(IV) oxide; malononitrile In dimethyl sulfoxide at 60℃; for 10h;
Stage #2: With potassium hydroxide In dimethyl sulfoxide at 110℃; for 12h; |
|
Reference：
[1]Kommula, Dileep; Li, Qing; Ning, Siyang; Liu, Wujun; Wang, Qian; Zhao, Zongbao K.
[Synthetic Communications, 2020, vol. 50, # 7, p. 1026 - 1034]
[2]Chen, Hui; Ding, Rui; Tang, Haitao; Pan, Yingming; Xu, Yanli; Chen, Yanyan
[Chemistry - An Asian Journal, 2019, vol. 14, # 19, p. 3264 - 3268]
[3]Broggi, Julie; Kosso, Anne Roly Obah; Redon, Sébastien; Vanelle, Patrice
[Synthesis, 2019, vol. 51, # 19, p. 3758 - 3764]
[4]Lin, Bizhen; Lu, Weiwei; Chen, Zhen-Yu; Zhang, Yue; Duan, Yin-Zhe; Lu, Xiaojie; Yan, Ming; Zhang, Xue-Jing
[Organic Letters, 2021, vol. 23, # 19, p. 7381 - 7385]
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[ 21856-94-0 ]
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[ 6750-04-5 ]
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3-(4-tolylselanyl)prop-2-yn-1-yl benzoate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 56% |
With copper(l) iodide In dimethyl sulfoxide at 25℃; for 24h; |
3-(Organochalcogenyl)prop-2-yn-1-yl)benzoates 3a-r and 3u; General Procedure
General procedure: In a reaction tube, under ambient atmosphere (air), containing theappropriated diorganyl diselenide 2 (0.15 mmol, 0.60 equiv, for 3u 1.2equiv) and CuI (10 mol%) at 25 °C was added DMSO (2 mL). To thestirred reaction mixture was added the proper benzoate 1 (0.25mmol) diluted in DMSO (1 mL), in one portion. The mixture wasstirred for the required time at 25 °C (Table 2). After that, the mixturewas quenched with sat. aq NH4Cl (5 mL) and the aqueous layer wasextracted with EtOAc (3 × 5 mL) and dried (MgSO4). After filtering, theorganic solution was concentrated using a rotary evaporator underreduced pressure |
Reference：
[1]Gritzenco, Fabiane; Kazmierczak, Jean C.; Anjos, Thiago; Sperança, Adriane; Peixoto, Maura L. B.; Godoi, Marcelo; Ledebuhr, Kauane N. B.; Brüning, César Augusto; Zamin, Lauren L.; Godoi, Benhur
[Synthesis, 2021, vol. 53, # 15, p. 2676 - 2688]
- 28
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[ 21856-94-0 ]
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[ 589-16-2 ]
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4-ethyl-2-(p-tolylselanyl)aniline
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 91% |
With iodine In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; regioselective reaction; |
Arylselenation of Anilines; General Procedure
General procedure: Aniline 1 (2 mmol), diselenide 2 (0.50 mmol) and I2 (0.506 g, were mixed in DMF (3 mL), then MS 4Å (100.0 mg) were added. Thereaction mixture was stirred at rt for 1-2 h under an open atmosphere.After completion of the reaction, the workup was done by extractingwith EtOAc and washing the combined EtOAc layers withbrine. After drying (Na2SO4) the combined EtOAc layers, the solventwas evaporated. The crude product thus obtained was purified by columnchromatography using silica gel (5% EtOAc in hexanes) to affordthe corresponding product 3 or 4 (Tables 2 and 3) |
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