- 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
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p. 2084 - 2088
(2021/03/01)
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- Metal-Free Synthesis of Unsymmetrical Aryl Selenides and Tellurides via Visible Light-Driven Activation of Arylazo Sulfones
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A protocol for the visible light driven preparation of unsymmetrical (hetero)aryl selenides and tellurides is described herein. The method exploits the peculiar photoreactivity of arylazo sulfones that act as thermally stable, precursors of aryl radicals under both photocatalyst- and additive-free conditions. The method developed shows an impressive versatility (more than fifty compounds isolated).
- Fagnoni, Maurizio,Li, Ankun,Li, Yuxuan,Liu, Junjie,Lu, Kui,Protti, Stefano,Shan, Xiwen,Tian, Miaomiao,Zhao, Xia
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supporting information
p. 7358 - 7367
(2020/12/01)
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- Metal-Free Synthesis of Phenol-Aryl Selenides via Dehydrogenative C-Se Coupling of Aryl Selenoxides with Phenols
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Herein, we disclose the synthesis of diaryl selenides through an unexpected C-Se coupling between aryl benzyl selenoxides and phenols. The synthetic significance of the method is that it provides a mild, rapid, and metal-free access to organoselenides in high yields with excellent functional group tolerance. This coupling of aryl benzyl selenoxides reveals a completely new reaction possibility compared with aryl sulfoxides. We also probed the reaction mechanism of this unexpected transformation through experimental studies and revealed a special Se(IV)-Se(III)-Se(II) reaction pathway.
- Liu, Zhengfen,Jiang, Yonggang,Liu, Chunxiang,Zhang, Linlin,Wang, Jing,Li, Tiantian,Zhang, Hongbin,Li, Minyan,Yang, Xiaodong
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p. 7386 - 7398
(2020/08/21)
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- Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
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An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
- Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
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p. 2707 - 2712
(2020/03/11)
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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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- 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
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supporting information
p. 1479 - 1484
(2018/05/03)
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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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- Silver-Catalyzed Synthesis of Diaryl Selenides by Reaction of Diaryl Diselenides with Aryl Boronic Acids
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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
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supporting information
p. 11472 - 11476
(2016/11/28)
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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
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supporting information
p. 777 - 781
(2016/03/12)
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- Synthesis of unsymmetrical diorganyl chalcogenides under greener conditions: Use of an iodine/DMSO system, solvent- and metal-free approach
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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.
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supporting information
p. 1446 - 1452
(2015/05/27)
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- A highly efficient and reusable MCM-41-immobilized bipyridine copper(I) catalyst for the C-Se coupling of organoboronic acids with diaryl diselenides
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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)
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- Copper-catalyzed C-Se coupling of diphenyl diselenide with arylboronic acids at room temperature
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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)
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- Glycerol as a recyclable solvent for copper-catalyzed cross-coupling reactions of diaryl diselenides with aryl boronic acids
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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
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supporting information; experimental part
p. 1030 - 1034
(2012/06/04)
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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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- Palladium-catalyzed cross-coupling of PhSeSnBu3 with aryl and alkyl halides in ionic liquids: A practical synthetic method of diorganyl selenides
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Palladium-catalyzed cross-coupling reactions of phenyl tributylstannyl selenide with aryl and alkyl halides can proceed smoothly in room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF 6]), to give the corresponding diorganyl selenides in good to high yields. The coupling reaction run in [bmim][PF6] has the advantages of rate acceleration and increase of yield in contrast to the reaction run in toluene. Our system not only avoids the use of easily volatile toluene as a solvent but also solves the basic problem of palladium catalyst reuse.
- Zhao, Hong,Hao, Wenyan,Xi, Zhiwen,Cai, Mingzhong
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experimental part
p. 2661 - 2665
(2012/01/04)
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- Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids
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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
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supporting information; experimental part
p. 2931 - 2938
(2011/11/29)
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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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- An efficient copper(I) iodide catalyzed synthesis of diaryl selenides through Cse bond formation using solvent acetonitrile as ligand
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A wide range of diaryl selenides can be synthesized through CSe bond formation using readily available copper(I) iodide as catalyst under mild reaction conditions (82C) from aryl iodides and diphenyl diselenide. In this coupling reaction, solvent acetonitrile acts as ligand for copper(I) iodide and no external ligand is required. Less reactive aryl bromides also provide the di-aryl selenides in good isolated yields. Georg Thieme Verlag Stuttgart ? New York.
- Dandapat, Arpan,Korupalli, Chiranjeevi,Prasad,Singh, Rahul,Sekar, Govindasamy
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experimental part
p. 2297 - 2302
(2011/09/16)
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- CuS/Fe: A novel and highly efficient catalyst system for coupling reaction of aryl halides with diaryl diselenides
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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
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supporting information; experimental part
p. 8583 - 8586
(2010/11/17)
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- Lewis acid InBr3-catalyzed arylation of diorgano diselenides and ditellurides with arylboronic acids
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A novel Lewis acid InBr3-catalyzed direct cross-coupling reaction of arylboronic acids with diorgano diselenides and ditellurides without any additive has been developed. The reactions generated the corresponding unsymmetrical diorgano monoselenides and monotellurides in good to excellent yields. The method has advantages of broad substrate scope, simple operation, mild reaction conditions and high effectiveness. A possible reaction mechanism was proposed. The Royal Society of Chemistry 2009.
- Ren, Kai,Wang, Min,Wang, Lei
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supporting information; experimental part
p. 4858 - 4861
(2010/02/16)
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- Iron-catalyzed ligand-free carbon-selenium (or tellurium) coupling of arylboronie acids with diselenides and ditellurides
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Carbon-selenium and carbon-tellurium cross-couplings of arylboronie acids with diselenides and ditellurides have been catalyzed by iron(0), iron(II) chloride or iron(III) chloride without any ligand and additive in the air. The method yields the corresponding unsymmetrical diorgano monoselenides and monotellurides in good to excellent yields, displays a broad substrate scope, and is simple, convenient, effective, economical and environmentally friendly.
- Wang, Min,Ren, Kai,Wang, Lei
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experimental part
p. 1586 - 1594
(2011/02/25)
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- Eco-friendly cross-coupling of diaryl diselenides with aryl and alkyl bromides catalyzed by CuO nanopowder in ionic liquid
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An eco-friendly cross-coupling reaction of aryl and alkyl bromides with diselenides using a catalytic amount of CuO nanopowder as a catalyst and an ionic liquid as a recyclable solvent is reported. The system shows high efficiency to catalyze this transformation, and in a green fashion due to the recyclable approach and the non-residual design protocol. This procedure has been utilized for the synthesis of a variety of diaryl selenides in good to excellent yields from the readily available aryl and alkyl bromides and diselenides. The Royal Society of Chemistry 2009.
- Singh, Devender,Alberto, Eduardo E.,Rodrigues, Oscar Endrigo Dorneles,Braga, Antonio Luiz
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experimental part
p. 1521 - 1524
(2010/06/13)
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- Copper oxide nanoparticle-catalyzed coupling of diaryl diselenide with aryl halides under ligand-free conditions
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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
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supporting information; experimental part
p. 951 - 953
(2009/07/11)
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- Lanthanum(III) oxide as a recyclable catalyst for the synthesis of diaryl sulfides and diaryl selenides
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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
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supporting information; experimental part
p. 5902 - 5905
(2010/03/02)
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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
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(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
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p. 1241 - 1245
(2007/10/03)
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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.
- -
-
Page/Page column 13-14; 37
(2008/06/13)
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- N-Phenylselenosaccharin (NPSSac): a new electrophilic selenium-containing reagent
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A new reagent N-phenylselenosaccharin (NPSSac) was simply prepared and used as a source of the electrophilic phenylselenyl group. This relatively stable new compound was able to react with a series of electron rich organic molecules like alkenes in the pr
- Tingoli, Marco,Diana, Rosita,Panunzi, Barbara
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p. 7529 - 7531
(2007/10/03)
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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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- 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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- Competing ene-reactions in the p-oxidation and o-phenylselenylation of phenol with benzeneseleninic acid
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Reaction of phenol with benzeneseleninic acid gives 2-(phenylseleno)- and 2,6-bis(phenylseleno)-1,4-benzoquinone via the corresponding 2- and 2,6-selenylated phenols; initiating ene-reactions are suggested for both the o-selenylation and the p-oxidation sequence.
- Henriksen, Lars
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p. 7057 - 7060
(2007/10/02)
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- Electrophilic Phenylselenenylation of Thiophenes. Synthesis of Poly(phenylseleno)thiophenes.
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The phenylselenenyl sulfate, generated from the oxidation of diphenyl diselenide with ammonium persulfate, easily effects electrophilic aromatic substituttion reactions on thiophene, 2-and 3-methylthiophenes and on 3-bromothiophene.The phenylseleno group
- Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Marini, Francesca,Mariggio, Stefania
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p. 10549 - 10554
(2007/10/02)
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- Synthesis of Selenoxides by Oxidation of Selenides with t-Butyl Hypochlorite, and Its Application for Synthesis of Optically Active Selenoxide
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An effective synthesis of selenoxides by the oxidation of selenides with t-butyl hypochlorite in the presence of methanol and pyridine followed by hydrolysis is described.This oxidation method is particularly effective for the oxidation of selenides which possess electron-withdrawing groups.A synthesis of partially optically active selenoxide with bulky substituents can be achieved using a novel oxidation method.
- Kobayashi, Michio,Ohkubo, Hiromi,Shimizu, Toshio
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p. 503 - 506
(2007/10/02)
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- PhSeCl AS A CHLORINATING AGENT FOR ACTIVATED BENZENE DERIVATIVES
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Regiospecific chlorination of some aromatic compounds using benzeneselenyl chloride are reported.
- Ayorinde, Folahan O.
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p. 2077 - 2078
(2007/10/02)
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- Direct Selenation of Electron-Rich Aromatic Compounds with (Phenylseleno)dimethylsulfonium Tetrafluoroborate
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(Phenylseleno)dimethylsulfonium tetrafluoroborate was found to be a highly reactive selenating agent for electron-rich aromatic compounds such as aromatic amines, phenols, and aromatic ethers.Reaction took place readily at 0-25 deg C to give ca. 50percent yields of substitution para to the activating substituent.In general, anilines gave better yields then anisoles or phenols.
- Gassman, Paul G.,Miura, Asako,Miura, Takashi
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p. 951 - 954
(2007/10/02)
-