65848-40-0Relevant articles and documents
Tellurium(II)/Tellurium(III)-Catalyzed Cross-Dehydrogenative C?N Bond Formation
Cremer, Christopher,Goswami, Monalisa,Rank, Christian K.,de Bruin, Bas,Patureau, Frederic W.
supporting information, p. 6451 - 6456 (2021/02/12)
The TeII/TeIII-catalyzed dehydrogenative C?H phenothiazination of challenging phenols featuring electron-withdrawing substituents under mild aerobic conditions and with high yields is described. These unexpected TeII/Tesu
Nickel(II) Tetraphenylporphyrin as an Efficient Photocatalyst Featuring Visible Light Promoted Dual Redox Activities
Mandal, Tanumoy,Das, Sanju,De Sarkar, Suman
supporting information, p. 3200 - 3209 (2019/05/16)
Nickel(II) tetraphenylporphyrin (NiTPP) is presented as a robust, cost-effective and efficient visible light induced photoredox catalyst. The ground state electrochemical data (CV) and electronic absorption (UV-Vis) spectra reveal the excited state redox potentials for [NiTPP]*/[NiTPP].? and NiTPP].+/[NiTPP]* couples as +1.17 V and ?1.57 V vs SCE respectively. The potential values represent NiTPP as a more potent photocatalyst compare to the well-explored [Ru(bpy)3]2+. The non-precious photocatalyst exhibits excited state redox reactions in dual fashions, i. e., it is capable of undergoing both oxidative as well as reductive quenching pathways. Such versatility of a photocatalyst based on first-row transition metals is very scarce. This unique phenomenon allows one to perform diverse types of redox reactions by employing a single catalyst. Two different sets of chemical reactions have been performed to represent the synthetic utility. The catalyst showed superior efficiency in both carbon-carbon and carbon-heteroatom bond-forming reactions. Thus, we believe that NiTPP is a valuable addition to the photocatalyst library and this study will lead to more practical synthetic applications of earth-abundant-metal-based photoredox catalysts. (Figure presented.).
Copper-catalyzed: Ipso -selenation of aromatic carboxylic acids
Wang, Jing,Li, Hongchen,Leng, Tao,Liu, Miaochang,Ding, Jinchang,Huang, Xiaobo,Wu, Huayue,Gao, Wenxia,Wu, Ge
, p. 9718 - 9726 (2017/11/30)
The copper-catalyzed decarboxylative selenation of aromatic carboxylic acids with diselenide is reported. This transformation tolerated a diverse set of functional groups on the substrates, including pentafluorobenzoic acid and heteroaromatic acids, delivering diaryl and methyl aryl selenides in good to excellent yields. Mechanistic studies indicated that the copper catalyst is essential in the activation of the Se-Se bond and the decarboxylation of aromatic acids. The utility of the products has been demonstrated in the facile synthesis of 10H-phenoselenazine and 11-methyldibenzo-(b,f)-1,4-selenazepine.
Visible light photocatalyzed direct conversion of aryl-/heteroarylamines to selenides at room temperature
Kundu, Debasish,Ahammed, Sabir,Ranu, Brindaban C.
supporting information, p. 1814 - 1817 (2014/04/17)
A novel strategy for the direct conversion of aryl- and heteroarylamines to selenides has been developed via diazotization of amines with tert-butyl nitrite in neutral medium followed by reaction with diaryl/diheteroaryl/dialkyl diselenides in one pot under photocatalysis at room temperature in the absence of any metal. This reaction is also applied for the synthesis of tellurides. The selenylation of heteroarylamine by this protocol is of much significance because of the difficulty in diazotization of these molecules by a standard diazotization method in acid medium.
Potassium tert-butoxide-mediated synthesis of unsymmetrical diaryl ethers, sulfides and selenides from aryl bromides
Kumar, Amit,Bhakuni, Bhagat Singh,Prasad, Ch. Durga,Kumar, Shailesh,Kumar, Sangit
, p. 5383 - 5392 (2013/07/04)
Potassium tert-butoxide mediated carbon-chalcogen C-E (E=O, S and Se) coupling reaction has been studied from aryl bromide and phenol/aryl disulfide/diselenide substrates. A series of unsymmetrical diaryl chalcogenides were accessed from aryl bromide and diaryl dichalcogenide precursors by using 2.5 equiv of potassium tert-butoxide in DMSO at 80 C. Unsymmetrical diaryl ethers were also obtained by using phenol precursors at 40-45 C. Aryl bromides with methyl, trifluoromethyl, methoxy and nitro substituents showed compatibility in the carbon-chalcogen bond forming reaction. 4-Methoxy, methyl, trifluoromethyl substituted bromobenzene substrates gave two regioisomers: 3-substituted and 4-substituted diaryl chalcogenides when reacted with phenols/diaryl disulfides/diselenides. Formation of two regioisomeric diaryl chalcogenides in the reaction mixture suggests that potassium tert-butoxide reacts with bromobenzene to produce benzyne intermediate, which subsequently reacts with diaryl dichalcogenides and finally give a regioisomeric mixture of 4-substituted and 3-substituted diaryl chalcogenides.
Synthesis of arylseleno-1,2,3-triazoles via copper-catalyzed 1,3-dipolar cycloaddition of azido arylselenides with alkynes
Deobald, Anna M.,Camargo, Leandro R.S.,Hoerner, Manfredo,Rodrigues, Oscar E.D.,Alves, Diego,Braga, Antonio L.
scheme or table, p. 2397 - 2406 (2011/09/15)
The use of organoselenium compounds in the copper-catalyzed Huisgen 1,3-dipolar cycloaddition of azido arylselenides with various alkynes is described. Arylseleno-1,2,3-triazoles are prepared in excellent yields via reaction of amino arylselenides with is
Synthesis of azido arylselenides and azido aryldiselenides: a new class of selenium-nitrogen compounds
Deobald, Anna Maria,Simon de Camargo, Leandro R.,Tabarelli, Greice,H?rner, Manfredo,Rodrigues, Oscar E.D.,Alves, Diego,Braga, Ant?nio L.
experimental part, p. 3364 - 3367 (2010/08/19)
We present here our results of the efficient synthesis of azido arylselenides and azido aryldiselenides under mild conditions. Starting from nitrogen-substituted benzenes, we incorporated selenium atom at aromatic ring and obtained amino arylselenides and diselenides in satisfactory yields. Treatment of these compounds with iso-pentyl nitrite (i-C5H11ONO) and azido trimethylsilane (Me3SiN3) in THF affords a variety of azido arylselenides and diselenides in good to excellent yields.
Methods for formation of aryl-sulfur and aryl-selenium compounds using copper(I) catalysts
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Page/Page column 17-18; 42, (2008/06/13)
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.
Magnesium-Induced Copper-Catalyzed Synthesis of Unsymmetrical Diaryl Chalcogenide Compounds from Aryl Iodide via Cleavage of the Se-Se or S-S Bond
Taniguchi, Nobukazu,Onami, Tetsuo
, p. 915 - 920 (2007/10/03)
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.
A general method for the formation of diaryl selenides using copper(I) catalysts
Gujadhur, Rattan K.,Venkataraman
, p. 81 - 84 (2007/10/03)
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.
