- Nickel-Catalyzed Intramolecular Decarbonylative Coupling of Aryl Selenol Esters
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This report describes a method for Ni-catalyzed intramolecular decarbonylative coupling, which enables the conversion of areneselenol esters to diaryl selenides. The inexpensive and readily available catalyst can be employed under mild reaction conditions for the construction of structurally diverse diaryl selenides, including heterocyclic and natural product derivatives. (Figure presented.).
- Bai, Jin-Hua,Qi, Xiu-Juan,Sun, Wei,Yu, Tian-Yang,Xu, Peng-Fei
-
supporting information
p. 2084 - 2088
(2021/03/01)
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- Photocatalyst-free photoredox synthesis of diaryl selenides by reaction of diselenides with aryldiazo sulfones
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A photcatalyst-free photoredox synthesis of diaryl selenides has been developed by coupling reaction of diselenides with aryldiazo sulfones. The reaction was accelerated under visible light irradiation without using a photocatalyst or photosensitizer. This approach facilitates the synthesis of diaryl selendes with a wide range of functional group tolerance.
- Jang, Jihoon,Kim, Rabin,Kim, Dae Young
-
supporting information
p. 720 - 726
(2020/11/30)
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- Trichloroisocyanuric Acid-Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature
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A transition-metal-free method for the synthesis of arylselenides and aryltellurides has been established based on the oxidative cross-coupling between diorganyl dichalcogenides and aryl boronic acids. With trichloroisocyanuric acid as an oxidant, the reaction proceeded smoothly to afford the desired products in 45–97% yields at ambient temperature. Three reaction reagents used in this method are stoichiometric and the oxidation by-product isocyanuric acid can be easily isolated and recovered. Besides of arylboronic acids, aryl trifluoroborates and aryl trihydroxyborates salts are also able to perform this transformation. (Figure presented.).
- Sun, Nan,Zheng, Kai,Sun, Pengyuan,Chen, Yang,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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p. 3577 - 3584
(2021/06/15)
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- Method for preparing asymmetric organic selenium ether compounds through metal-free chemical oxidation method (by machine translation)
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The method is mild in reaction condition, convenient to operate, high in 1 reaction condition, convenient 2 to operate, high in safety, wide in substrate range, high 2 - 8h in yield, particularly suitable for reaction of various poor 3 electric and sterically hindered arylboronic acid and diselenoxy ether, and capable of finishing most of the reaction 4h. (by machine translation)
- -
-
Paragraph 0059-0063
(2020/12/09)
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- New routes for the synthesis of unsymmetrical diarylselenides: Effect of heat, light and ultrasound
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Herein, we report the photochemical coupling of diphenyldiselenides with substituted phenylhydrazine hydrochloride without catalyst. The protocol was developed not only in presence of sunlight and UV light but also under thermal condition for comparison study. Moreover, ultrasound assisted new catalytic protocol was developed using Ni(II)/L-proline system in DMSO with the advantage of shorter reaction time compared to earlier reports. We have also developed a new C-Se cross coupling reaction where phenylselenyl chloride and arylhydrazine hydrochlorides were effectively coupled using developed catalytic system.
- Sahani, Amber J.,Burange, Anand S.,Thakur, Seema D.,Jayaram, Radha V.
-
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- Copper-Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N-Thiophthalimides Leading to Polyfunctional Thioethers
-
(Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N-thiophthalimides at 25 °C within 1 h in the presence of 5–10 % Cu(OAc)2?H2O to furnish the corresponding polyfunctionalized thioethers in good yields. This electrop
- Gra?l, Simon,Hamze, Clémence,Koller, Thadd?us J.,Knochel, Paul
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p. 3752 - 3755
(2019/02/13)
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- Syntheses of Thioethers and Selenide Ethers from Anilines
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In this study, a general procedure was proposed for synthesizing thioethers and selenide ethers from anilines under solvent-free and transition-metal-free conditions. Thioethers were formed when anilines reacted with thiols under blue light-emitting-diode (LED) irradiation at room temperature without a photocatalyst. When reactions were performed using anilines and diselenides, the corresponding selenide ethers were obtained with satisfactory to excellent yields. The reaction was performed under photocatalyst-free and solvent-free conditions without blue LEDs. The advantages of this system include convenient operations, mild reaction conditions, satisfactory functional group tolerance, and late-stage selenylation of drug molecules.
- Shieh, Yi-Chen,Du, Kai,Basha, R. Sidick,Xue, Yung-Jing,Shih, Bo-Hao,Li, Liang,Lee, Chin-Fa
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p. 6223 - 6231
(2019/05/24)
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- Efficient heterogeneous copper-catalysed C–Se coupling of aryl iodides with symmetrical diselenides towards unsymmetrical monoselenides
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A highly efficient heterogeneous copper(I)-catalysed C–Se coupling of aryl iodides with diaryl diselenides was achieved in dimethylformamide at 110 °C under neutral conditions by using a 10 mol% of bipyridine-functionalised MCM-41-supported copper(I) complex [bpy-MCM-41-CuI] as the catalyst and magnesium as the reductive reagent, yielding a variety of unsymmetrical diaryl selenides in good to excellent yields. This heterogeneous copper catalyst can be easily recovered by a simple filtration of the reaction solution and recycled at least seven times without significant loss of activity.
- Zhao, Ruonan,Yan, Chenyu,Jiang, Yuanyuan,Cai, Mingzhong
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p. 584 - 588
(2018/11/27)
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- Synthesis of Diaryl Selenides via Palladium-Catalyzed Debenzylative Cross-Coupling of Aryl Benzyl Selenides with Aryl Bromides
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Herein, we report a novel method for synthesizing diaryl selenides from aryl benzyl selenides and aryl bromides via debenzylative cross-coupling with a Pd/NIXANTPHOS-catalyst. NIXANTPHOS outperformed other commonly used bi- and monodentate ligands examined in this novel transformation. This reaction system displays wide functional group tolerance and excellent substrate scope. The transformation broadens the scope of palladium-catalyzed debenzylative processes to use selenolate anions as a leaving group. Its potential for practical synthetic applications was demonstrated with the gram scale synthesis of 4-chlorophenyl phenyl selenide.
- Wang, Hao,Chen, Shuguang,Liu, Guoqing,Guan, Haixing,Zhong, Daoyin,Cai, Jun,Zheng, Zhipeng,Mao, Jianyou,Walsh, Patrick J.
-
supporting information
p. 4086 - 4091
(2018/11/21)
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- Merging visible-light photoredox and micellar catalysis: Arylation reactions with anilines nitrosated in situ
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An aqueous photocatalytic system was designed by merging visible-light photoredox catalysis with micellar catalysis. Eosin B, an organic dye, was utilized as the photocatalyst, and Triton X-100 was employed as the surfactant; both are inexpensive and commercially available. This clean and energy-saving catalytic system enables photocatalytic reactions of the diazonium ion generated in situ to proceed smoothly in water without any co-solvents or additives at room temperature.
- Bu, Mei-Jie,Lu, Guo-Ping,Jiang, Jianzhong,Cai, Chun
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p. 3728 - 3732
(2018/08/12)
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- Alternative Metal-Free Synthesis of Diorganoyl Selenides and Tellurides Mediated by Oxone
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We herein describe an alternative metal-free methodology for the synthesis of diorganyl selenides and tellurides mediated by Oxone . The products were obtained in moderate to excellent yields by reactions of diorganyl diselenides or ditellurides with aryl boronic acids mediated by Oxone with use of EtOH as the solvent. The methodology is applicable to a broad scope of diorganyl dichalcogenides and aryl boronic acids containing electron-rich, electron-poor, and sterically hindered substituents.
- Perin, Gelson,Duarte, Luis Fernando B.,Neto, José S. S.,Silva, Márcio S.,Alves, Diego
-
supporting information
p. 1479 - 1484
(2018/05/03)
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- Atom-Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides
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An atom-economical method for the synthesis of unsymmetrical diaryl selenides from arylhydrazines and stoichiometric amounts of diselenides was developed under mild conditions. The new and facile selenide synthesis involved the use of an inexpensive base in air to form unsymmetrical diaryl selenides in good yields. This C–Se radical arylation of diaryl diselenides was performed by forming aryl radicals from arylhydrazines under oxidative conditions. The formation of a phenyl radical was supported by trapping with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) in air. Therefore, this synthesis might involve a homolytic aromatic substitution (HAS) mechanism. The synthesis is both low costing and environmentally friendly and, therefore, may be useful for the practical synthesis of unsymmetrical diaryl selenides.
- Taniguchi, Toshihide,Murata, Akinori,Takeda, Motonori,Mizuno, Takumi,Nomoto, Akihiro,Ogawa, Akiya
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p. 4928 - 4934
(2017/09/13)
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- Copper-catalyzed synthesis of unsymmetrical diorganyl chalcogenides (Te/Se/S) from boronic acids under solvent-free conditions?
-
The efficient and mild copper-catalyzed synthesis of unsymmetrical diorganyl chalcogenides under ligand- and solvent-free conditions is described. The cross-coupling reaction was performed using aryl boric acids and 0.5 equiv. of diorganyl dichalcogenides (Te/Se/S) in the presence of 3 mol % of CuI and 3 equiv. of DMSO, under microwave irradiation. This new protocol allowed the preparation of several unsymmetrical diorganyl chalcogenides in good to excellent yields.
- Saba, Sumbal,Botteselle, Giancarlo Vaccari,Godoi, Marcelo,Frizon, Tiago Elias Allievi,Galetto, Fábio Zazyki,Rafique, Jamal,Braga, Antonio L.
-
-
- Synthesis of Unsymmetrical Diaryl Selenides: Copper-Catalyzed Se-Arylation of Diaryl Diselenides with Triarylbismuthanes
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Copper-catalyzed C(aryl)-Se bond formation by the reaction of diaryl diselenides with triarylbismuthanes in the presence of copper(I) acetate (10 mol%) and 1,10-phenanthroline (10 mol%) under aerobic conditions led to the formation of unsymmetric diaryl s
- Matsumura, Mio,Shibata, Kohki,Ozeki, Sota,Yamada, Mizuki,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
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p. 730 - 736
(2016/03/01)
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- A Highly Efficient Copper-Catalyzed Synthesis of Unsymmetrical Diaryl- and Aryl Alkyl Chalcogenides from Aryl Iodides and Diorganyl Disulfides and Diselenides
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An efficient and convenient protocol has been developed for the copper-catalyzed reaction of aryl iodides and diorganyl disulfides and diselenides. A variety of symmetrical and unsymmetrical diaryl- and aryl alkyl chalcogenides were synthesized with good functional group tolerance and chemoselectivity by using copper(I) iodide as a catalyst, 4′-(4-methoxyphenyl)-2,2′:6′,2′′-terpyridine as ligand, and KOH as base under an inert atmosphere.
- Movassagh, Barahman,Hosseinzadeh, Zhila
-
supporting information
p. 777 - 781
(2016/03/12)
-
- Silver-Catalyzed Synthesis of Diaryl Selenides by Reaction of Diaryl Diselenides with Aryl Boronic Acids
-
We described herein our results on the silver-catalyzed synthesis of diaryl selenides via a cross-coupling reaction of diaryl diselenides with aryl boronic acids. The methodology is tolerant to electron-donor and electron-withdrawing groups at the substrates and the desired products were obtained in good to excellent yields.
- Goldani, Bruna,Ricordi, Vanessa G.,Seus, Natália,Lenard?o, Eder J.,Schumacher, Ricardo F.,Alves, Diego
-
supporting information
p. 11472 - 11476
(2016/11/28)
-
- Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert -Butyl Nitrite
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A mild, metal-free synthesis of aryl sulfides has been disclosed. Aryl diazonium ion was generated by the in situ nitrosation of aniline, and it was reduced by ascorbic acid (vitamin C) to form aryl radical, which underwent a thiolation with disulfide to yield aryl sulfide. The reaction proceeded smoothly without heating or irradiation. This strategy was also expanded to the synthesis of aryl selenides.
- Bu, Mei-Jie,Lu, Guo-Ping,Cai, Chun
-
supporting information
p. 1841 - 1846
(2015/08/06)
-
- A highly efficient and reusable MCM-41-immobilized bipyridine copper(I) catalyst for the C-Se coupling of organoboronic acids with diaryl diselenides
-
A highly efficient MCM-41-immobilized bipyridine copper(i) complex [MCM-41-bpy-CuI] was prepared from 4,4'-bis[3-(triethoxysilyl)propylaminomethyl]-2,2'-bipyridine via immobilization on the mesoporous material MCM-41, followed by reaction with CuI. In the presence of 5 mol% MCM-41-bpy-CuI, the cross-coupling reaction of organoboronic acids with diaryl diselenides proceeded smoothly in DMSO/H2O (2/1) at 110°C under air to afford a variety of diorganyl selenides in good to excellent yields. This heterogeneous copper catalyst can be recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decrease in activity.
- Zhao, Hong,Jiang, Yuanyuan,Chen, Qiurong,Cai, Mingzhong
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p. 2106 - 2115
(2015/03/18)
-
- Synthesis of unsymmetrical diorganyl chalcogenides under greener conditions: Use of an iodine/DMSO system, solvent- and metal-free approach
-
Herein, we report a greener iodine-catalyzed protocol to access different types of unsymmetrical diorganyl chalcogenides. This new approach works in the absence of solvent and metal. The desired products were obtained in good to excellent yields using one equivalent of arylboronic acids, half an equivalent of various diorganyl dichalcogenides, iodine (10 mol%) as a catalyst and 2 equivalents of dimethyl sulfoxide (DMSO; as oxidant), with a reaction time of 10 min under microwave irradiation.
- Saba, Sumbal,Rafique, Jamal,Braga, Antonio L.
-
supporting information
p. 1446 - 1452
(2015/05/27)
-
- Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts
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We describe here a simple and catalyst-free method to synthesize diaryl selenides by reaction of arenediazonium tetrafluoroborate salts with arylselenols, generated in situ by using diaryl diselenides and hypophosphorous acid (H3PO2), using THF as solvent. This is a direct nucleophilic aromatic substitution (SNAr) reaction performed with diaryl diselenides and arenediazonium salts bearing electron-withdrawing and electron-donating groups affording the corresponding diaryl selenides in moderated to good yields.
- Balaguez, Renata A.,Ricordi, Vanessa Gentil,Freitas, Camilo S.,Perin, Gelson,Schumacher, Ricardo F.,Alves, Diego
-
supporting information
p. 1057 - 1061
(2014/02/14)
-
- Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts
-
We describe here a simple and catalyst-free method to synthesize diaryl selenides by reaction of arenediazonium tetrafluoroborate salts with arylselenols, generated in situ by using diaryl diselenides and hypophosphorous acid (H3PO2), using THF as solvent. This is a direct nucleophilic aromatic substitution (SNAr) reaction performed with diaryl diselenides and arenediazonium salts bearing electron-withdrawing and electron-donating groups affording the corresponding diaryl selenides in moderated to good yields.
- Balaguez, Renata A.,Ricordi, Vanessa Gentil,Freitas, Camilo S.,Perin, Gelson,Schumacher, Ricardo F.,Alves, Diego
-
supporting information
p. 1057 - 1061
(2015/02/19)
-
- A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
-
A simple and convenient approach for the synthesis of unsymmetrical diaryl chalcogenides (Te, Se, and S) has been developed by copper-catalyzed cross-coupling reaction of organoboronic acid with diaryl dichalcogenide in ethanol using NaBH4 in air or oxygen. The present methodology is highly practical for the synthesis of unsymmetrical diaryl tellurides with various functionalities such as -NO2, -F, -Br, and -COOH that have been obtained in good to excellent yields. Methodology is also effective for the synthesis of unsymmetrical diaryl selenides and sulfides. Moreover, symmetrical diaryl selenides have also been obtained from arylboronic acids using elemental selenium powder under optimized reaction conditions. The use of NaBH 4 is the key for the development of milder reaction conditions, which enable the construction of unsymmetrical diaryl chalcogenides from boronic acid substrates in ethanol at room temperature.
- Kumar, Amit,Kumar, Sangit
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p. 1763 - 1772
(2014/03/21)
-
- Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides
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A novel method of photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides has been developed. Although the arylation reactions with triarylbismuthines are usually catalyzed by transition-metal complexes, the present arylation of diaryl diselenides with triarylbismuthines proceeds upon photoirradiation in the absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method.
- Kobiki, Yohsuke,Kawaguchi, Shin-Ichi,Ohe, Takashi,Ogawa, Akiya
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p. 1141 - 1147
(2013/07/26)
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- Transition-metal-free synthesis of unsymmetrical diaryl chalcogenides from arenes and diaryl dichalcogenides
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A transition-metal-free synthetic method has been developed for the synthesis of unsymmetrical diaryl chalcogenides (S, Se, and Te) from diaryl dichalcogenides and arenes under oxidative conditions by using potassium persulfate at room temperature. Variously substituted arenes such as anisole, thioanisole, diphenyl ether, phenol, naphthol, di- and trimethoxy benzenes, xylene, mesitylene, N,N-dimethylaniline, bromine-substituted arenes, naphthalene, and diaryl dichalcogenides underwent carbon-chalcogen bond-forming reaction to give unsymmetrical diaryl chalcogenides in trifluoroacetic acid. To understand the mechanistic part of the reaction, a detailed in situ characterization of the intermediates has been carried out by 77Se NMR spectroscopy by using diphenyl diselenide as the substrate. 77Se NMR study suggests that electrophilic species ArE+ is generated by the reaction of diaryl dichalcogenide with persulfate in trifluoroacetic acid. The electrophilic attack of arylchalcogenium ion on the arene may be responsible for the formation of the aryl-chalcogen bond.
- Prasad, Ch Durga,Balkrishna, Shah Jaimin,Kumar, Amit,Bhakuni, Bhagat Singh,Shrimali, Kaustubh,Biswas, Soumava,Kumar, Sangit
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p. 1434 - 1443
(2013/03/29)
-
- Copper-catalyzed C-Se coupling of diphenyl diselenide with arylboronic acids at room temperature
-
An efficient synthetic protocol for the Cu-catalyzed cross-coupling of diphenyl diselenide and arylboronic acid at room temperature was described. This catalytic system could tolerate a variety of arylboronic acids with only 3 mol % amount of CuSO4 as the catalyst and inexpensive 1,10-phen. H 2O as the ligand. Moreover, this catalytic system used environment-friendly EtOH as the solvent and catalytic amount of Na 2CO3 (20 mol %) as the base in the air.
- Zheng, Bo,Gong, Ying,Xu, Hua-Jian
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p. 5342 - 5347
(2013/06/27)
-
- Magnetically separable CuFe2O4 nanoparticle catalyzed CSe cross coupling in reusable PEG medium
-
A simple and efficient procedure for the synthesis of unsymmetrical diaryl selenides has been developed by magnetically separable CuFe2O 4 nanoparticle catalyzed reactions of organoboranes with PhSeBr in recyclable PEG-400 medium at 80 °C and Cs2CO3 as base. Using this protocol, a variety of unsymmetrical selenides were obtained in good to excellent yields. The copper ferrite nanoparticles were magnetically separated, recycled, and reused up to four cycles.
- Harsha Vardhan Reddy,Satish,Ramesh,Karnakar,Nageswar
-
experimental part
p. 585 - 587
(2012/07/30)
-
- Glycerol as a recyclable solvent for copper-catalyzed cross-coupling reactions of diaryl diselenides with aryl boronic acids
-
We describe herein the use of glycerol as the solvent in the copper-catalyzed cross-coupling reaction of diaryl diselenides with arylboronic acids using CuI and DMSO as additive. This cross-coupling reaction was performed with diaryl diselenides and arylboronic acids bearing electron-withdrawing and electron-donating groups, affording the corresponding diaryl selenides in good to excellent yields. The glycerol-CuI mixture can be directly reused for further cross-coupling reactions.
- Ricordi, Vanessa G.,Freitas, Camilo S.,Perin, Gelson,Lenardao, Eder J.,Jacob, Raquel G.,Savegnago, Lucielli,Alves, Diego
-
supporting information; experimental part
p. 1030 - 1034
(2012/06/04)
-
- Magnetically separable and reusable copper ferrite nanoparticles for cross-coupling of aryl halides with diphenyl diselenide
-
A simple and efficient procedure for the synthesis of diaryl selenides has been developed by a copper ferrite nanoparticle catalyzed reaction of aryl iodides/aryl bromides with diphenyl diselenide in the presence of base and solvent at 120 °C. Using this protocol, a variety of diselenides were obtained in good to excellent yields. The copper ferrite nanoparticles were magnetically separated, recycled, and reused up to three cycles. Copyright
- Swapna, Kokkirala,Murthy, Sabbavarapu Narayana,Nageswar, Yadavalli Venkata Durga
-
experimental part
p. 1940 - 1946
(2011/04/27)
-
- Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids
-
We described herein the use of imidazolium ionic liquids [bmim]PF 6 and [bmim]BF4 in the selective, metal and catalyst-free synthesis of unsymmetrical diaryl selenides by electrophilic substitution in arylboron reagents with arylselenium halides (Cl and Br) at room temperature. This is a general substitution reaction and it was performed with arylboronic acids or potassium aryltrifluoroborates bearing electron-withdrawing or electron-donating groups, affording the corresponding diaryl selenides in good to excellent yields. The ionic liquid [bmim][PF6] was easily recovered and utilized for further substitution reactions.
- Freitas, Camilo S.,Barcellos, Angelita M.,Ricordi, Vanessa G.,Pena, Jesus M.,Perin, Gelson,Jacob, Raquel G.,Lenardao, Eder J.,Alves, Diego
-
supporting information; experimental part
p. 2931 - 2938
(2011/11/29)
-
- CuS/Fe: A novel and highly efficient catalyst system for coupling reaction of aryl halides with diaryl diselenides
-
The CuS catalyzed coupling reactions of aryl halides and diaryl diselenides were accelerated by the addition of Fe powder in only 3-12 h with good to excellent yields. SEM-EDX indicated that the in situ iron oxides as support against catalyst agglomeration accelerated the reaction. This catalyst system was also demonstrated recyclable without significant loss of catalytic activity.
- Li, Yaming,Wang, Huifeng,Li, Xiaoying,Chen, Tao,Zhao, Defeng
-
supporting information; experimental part
p. 8583 - 8586
(2010/11/17)
-
- Copper oxide nanoparticle-catalyzed coupling of diaryl diselenide with aryl halides under ligand-free conditions
-
A new, efficient and ligand-free cross-coupling reaction of aryl halides and diaryl diselenides using a catalytic amount of nanocrystalline CuO as a recyclable catalyst with KOH as the base in DMSO at 110 °C is reported. This protocol has been utilized for the synthesis of a variety of aryl selenides in excellent yields from the readily available aryl halides and diaryl diselenides.
- Reddy, Vutukuri Prakash,Kumar, Akkilagunta Vijay,Swapna, Kokkirala,Rao, Kakulapati Rama
-
supporting information; experimental part
p. 951 - 953
(2009/07/11)
-
- Lanthanum(III) oxide as a recyclable catalyst for the synthesis of diaryl sulfides and diaryl selenides
-
La2O3 as a new and efficient recyclable catalyst in coupling various aryl halides with aromatic/alkyl thiols and diphenyl diselenide in combination with KOH as a base and DMEDA as a ligand in DMSO at 110 °C is reported.
- Murthy, Sabbavarapu Narayana,Madhav, Bandaru,Reddy, Vutukuri Prakash,Nageswar, Yadavalli Venkata Durga
-
supporting information; experimental part
p. 5902 - 5905
(2010/03/02)
-
- CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids
-
We present here an efficient and ligand-free cross-coupling reaction of organic diselenides with aryl boronic acids using a catalytic amount of CuO nanoparticles in DMSO at 100 °C under air atmosphere. This is a general cross-coupling reaction and was performed with organic diselenides and aryl boronic acids bearing electron-withdrawing and electron-donating groups affording the corresponding selenides in good to excellent yields. The CuO nanoparticles can be easily recovered and utilized for further catalytic reactions.
- Alves, Diego,Santos, Cayane G.,Paix?o, Márcio W.,Soares, Letiére C.,Souza, Diego de,Rodrigues, Oscar E.D.,Braga, Ant?nio L.
-
scheme or table
p. 6635 - 6638
(2010/03/01)
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- Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogenides via cleavage of the S-S, Se-Se, or Te-Te bond by a copper catalyst
-
(Chemical Equation Presented) This article describes the methodology for a copper-catalyzed preparation of numerous monochalcogenides from dichalcogenides with organoboronic acids. Unsymmetrical diorgano-monosulfides, selenides, and tellurides can be synthesized by the coupling of dichalcogenides with aryl- or alkylboronic acids using a copper catalyst in air. The present reaction can take advantage of both organochalcogenide groups on dichalcogenide.
- Taniguchi, Nobukazu
-
p. 1241 - 1245
(2007/10/03)
-
- Palladium-catalyzed phenyl-selenylation with n-Bu3SnSePh in one-pot two-step reactions
-
We have studied the Pd-catalyzed cross-coupling reaction of a stannane derived from selenium n-Bu3SnSePh (1) with aryl and perfluoroalkyl iodides. Herein a very efficient one-pot two-step selenylation reaction to form a C-Se bond is reported. Ph2Se2 reacts with Na metal in liquid ammonia yielding PhSe- ions. To this solution n-Bu3SnCl was added to afford 1, which was introduced in the palladium-catalyzed coupling reaction without isolation. These reactions afford functionalized diarylselenides and phenylperfluroalkyl selenides from good to high yields (38-98%).
- Bonaterra, Mariana,Martín, Sandra E.,Rossi, Roberto A.
-
p. 3511 - 3515
(2007/10/03)
-
- Zinc-mediated synthesis of diaryl selenides from diaryl diselenides and diaryliodonium salts in aqueous media
-
An efficient synthetic method has been developed for the preparation of symmetrical and unsymmetrical diaryl selenides through a one-pot reaction of diaryl diselenides and diaryliodonium salts in the presence of Zn/AlCl 3 system in aqueous media.
- Movassagh, Barahman,Fazeli, Azadeh
-
p. 194 - 196
(2007/10/03)
-
- A simple copper salt-catalyzed synthesis of unsymmetrical diaryl selenides and tellurides from arylboronic acids with diphenyl diselenide and ditelluride
-
In the presence of a catalytic amount of simple copper salt, the reaction of arylboronic acids with diphenyl diselenide and ditelluride was accomplished without any additive to afford the corresponding unsymmetrical diarylselenides and tellurides in good yields. Georg Thieme Verlag Stuttgart.
- Wang, Lei,Wang, Min,Huang, Fuping
-
p. 2007 - 2010
(2007/10/03)
-
- Insertion of selenium into zinc carbon bonds and its application in the synthesis of unsymmetrical diarylselenides
-
Selenium inserts into the zinc carbon bond of aryl zinc halides to form the corresponding zinc selenoates; these react in THF-HMPA with diaryliodonium salts to afford unsymmetrical diaryl selenides in good yields.
- Xu, Xin-Hua,Liu, Wen-Qi
-
p. 444 - 445
(2007/10/03)
-