- Electrochemical Radical Selenylation of Alkenes and Arenes via Se-Se Bond Activation
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A novel electrochemical radical selenylation of alkenes and activated arenes without external oxidants is reported. The diselenide was fully transformed into Se-centered radicals through electrochemical Se-Se bond activation. Three-component radical carbonselenation was successfully realized using styrenes to trap the RSe radical. Besides, the direct coupling of RSe radicals with activated arenes was further developed. Using this atom-economic protocol, diversity of unsymmetric aryl-aryl, aryl-alkyl, and alkyl-alkyl selenoethers was obtained regioselectively, which has potential application in biological chemistry.
- Sun, Li,Wang, Liwei,Alhumade, Hesham,Yi, Hong,Cai, Hu,Lei, Aiwen
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supporting information
p. 7724 - 7729
(2021/10/20)
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- 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 general and green procedure for the synthesis of organochalcogenides by CuFe2O4 nanoparticle catalysed coupling of organoboronic acids and dichalcogenides in PEG-400
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A general and efficient procedure has been developed for the synthesis of organochalcogenides (selenides and tellurides) by a simple reaction of organoboronic acids and dichalcogenides catalysed by CuFe2O 4 nanoparticles in PEG-400 without any ligand. This protocol offers the scope for access to a wide spectrum of chalcogenides including diaryl, aryl-heteroaryl, aryl-styrenyl, aryl-alkenyl, aryl-allyl, aryl-alkyl and aryl-alkynyl versions. The catalyst is magnetically separable and recyclable eight times without any loss of appreciable catalytic activity. The products are obtained in high purities after evaporation of solvent followed by filtration column chromatography. The Royal Society of Chemistry.
- Kundu, Debasish,Mukherjee, Nirmalya,Ranu, Brindaban C.
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p. 117 - 125
(2013/04/10)
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- Magnetically separable CuFe2O4 nanoparticle catalyzed CSe cross coupling in reusable PEG medium
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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
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experimental part
p. 585 - 587
(2012/07/30)
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- Electrophilic organic selenium reagents - Protonated seleninic acids as precursors for unsymmetrical aromatic selenides
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Arylselenylations of methylbenzenes, methoxybenzenes and thiophene were smoothly achieved with selenenium ions generated by comproportionation of 1:1 mixtures of p-toluenesulfonic acid salts of seleninic acids and the corresponding diselenides. A series of p-toluenesulfonic salts of seleninic acids were prepared by hydrogen peroxide oxidation of the corresponding diselenides in the presence of p-toluenesulfonic acid. Novel 2-(organylseleno)thiophenes were obtained by heating the protonated seleninic acids with a 50-fold excess of thiophene in glacial acetic acid.
- Stuhr-Hansen, Nicolai,S?lling, Theis Ivan,Henriksen, Lars
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experimental part
p. 2633 - 2643
(2011/04/25)
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- Magnetically separable and reusable copper ferrite nanoparticles for cross-coupling of aryl halides with diphenyl diselenide
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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
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experimental part
p. 1940 - 1946
(2011/04/27)
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- Al2O3-Supported Cu-catalyzed electrophilic substitution by PhSeBr in organoboranes, organosilanes, and organostannanes. A protocol for the synthesis of unsymmetrical diaryl and alkyl aryl selenides
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(Figure Presented) Alumina-supported copper sulfate efficiently catalyzes electrophilic substitution in organoborane, organosilanes, and organostannanes by phenylselenium bromide providing a novel and efficient route to the synthesis of unsymmetrical diaryl and alkyl aryl selenides. A series of aryl, alkyl, and heteroaryl phenyl selenides were obtained in high yields. The catalyst is inexpensive, eco- and user-friendly, and recyclable. The mechanism involving Cu-assisted nucleophilic displacement of Br in PhSeBr by mild nucleophiles is described.
- Bhadra, Sukalyan,Saha, Amit,Ranu, Brindaban C.
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experimental part
p. 4864 - 4867
(2010/10/18)
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- Methods for formation of aryl-sulfur and aryl-selenium compounds using copper(I) catalysts
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A mild, palladium-free synthetic protocol for the cross-coupling reaction of vinyl or aryl iodides and thiols or selenols using, in certain embodiments, 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 ° C. A variety of vinyl/aryl sulfides and vinyl/aryl selenides can be synthesized in excellent yields from readily available iodides and thiols or selenols.
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Page/Page column 15-16; 38-39
(2008/06/13)
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- Magnesium-Induced Copper-Catalyzed Synthesis of Unsymmetrical Diaryl Chalcogenide Compounds from Aryl Iodide via Cleavage of the Se-Se or S-S Bond
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The methodology for a copper-catalyzed preparation of diaryl chalcogenide compounds from aryl iodides and diphenyl dichalcogenide molecules is reported. Unsymmetrical diaryl sulfide or diaryl selenide can be synthesized from aryl iodide and PhYYPh (Y = S, Se) with a copper catalyst (CuI or Cu2O) and magnesium metal in one pot. This reaction can be carried out under neutral conditions according to an addition of magnesium metal as the reductive reagent. Furthermore, it is efficiently available for two monophenylchalcogenide groups generated from diphenyl dichalcogenide.
- Taniguchi, Nobukazu,Onami, Tetsuo
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p. 915 - 920
(2007/10/03)
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- A general method for the formation of diaryl selenides using copper(I) catalysts
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We report a mild, palladium-free synthetic protocol for the cross coupling reaction of aryl iodides and phenyl selenol using 10 mol% CuI/neocuproine, NaOt-Bu or K2CO3 as base, in toluene, at 110°C. Using this protocol, we show that a variety of diaryl selenides can be synthesized in good yields from commercially available aryl iodides.
- Gujadhur, Rattan K.,Venkataraman
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- Copper-catalyzed synthesis of diaryl selenide from aryl iodide and diphenyl diselenide using magnesium metal
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Various unsymmetrical diaryl selenides can be synthesized from aryl iodides and diphenyl diselenide by an addition of magnesium metal in the presence of a copper catalyst. This method can exploit efficiently two phenylselenide-molecules generated from diphenyl diselenide under neutral conditions.
- Taniguchi, Nobukazu,Onami, Tetsuo
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p. 829 - 832
(2007/10/03)
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- Preparation and interconversion of phenylselenenylated and alkyjlselenenylated aromatic compounds
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Phenylselenenyl and alkylselenenyl sulfates were found to efficiently and mildly introduce one or several phenylselenenyl or alkylselenenyl groups into activated aromatic or heteroaromatic compounds. When treated with methylselenenyl sulfate, veratrole an
- Engman, Lars,Eriksson, Per
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p. 861 - 871
(2007/10/03)
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- NOVEL HALOGENATION OF THIOPHENES WITH BENZENESELENINYL CHLORIDE AND ALUMINUM HALIDE
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In the presence of aluminum halide, benzeneseleninyl chloride is an efficient regioselective halogenating reagent for heterocyclic compounds such as thiophene, 2-methylthiophene, 3-methylthiophene, 2,5-dimethylthiophene, and furan.In the case of pyrrole, no halogenated product was obtained.A plausible reaction mechanism involving a positive halogen intermediate is proposed.
- Kamigata, Nobumasa,Suzuki, Takashi,Yoshida, Masato
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