- Visible Light-Promoted Selenylation/Cyclization of Enaminones toward the Formation of 3-Selanyl-4H-Chromen-4-Ones
-
A simple and efficient visible-light-promoted selenylation/cyclization of enaminones have been realized for the practical synthesis of 3-selanyl-4H-chromen-4-ones. This reaction is performed in the mild conditions, no transition metal catalyst or photocatalysts and no additional oxidants are required. In addition, the 3-selanyl-4H-chromen-4-ones could be easily converted to selanyl-functionalized pyrimidines by reacting with benzamidine substrates. (Figure presented.).
- Liu, Hao-Yang,Zhang, Jia-Rong,Huang, Guo-Bao,Zhou, Yi-Huan,Chen, Yan-Yan,Xu, Yan-Li
-
supporting information
p. 1656 - 1661
(2021/02/12)
-
- Green preparation method of aryl diselenium ether type organic selenium compound
-
The invention discloses an aryl diselenium ether compound synthesis method. The synthesis method comprises the following steps: taking the compound represented by the formula (I) as a reaction raw material, CuBr as a catalyst, KOH in the condition Se, a reducing agent, a disproportionation reaction, water or ethanol as a solvent, and 60 °C. After completion of the reaction, the obtained reaction solution is subjected to post-treatment (if ethanol is recovered as solvent) to obtain the aryl diselenoether compound represented by the formula (II), the yield is close 100%, the subsequent treatment is simple, and a complex separation and purification method is not needed to obtain a pure product. The solvent is recovered as a solvent such as ethanol. , It is preferable. The method is more green. Economy, high efficiency, environmental protection.
- -
-
Paragraph 0042-0046
(2021/11/14)
-
- Metal-free chalcogenation of cycloketone oxime esters with dichalcogenides
-
We report the metal-free chalcogenation of cycloketone oxime esters with dichalcogenides via a radical process. Because of the metal-free condition and use of readily accessible dichalcogenides, this method is an effective and green strategy for the synthesis of chalcogen-substituted butyronitrile.
- Ji, Liangshuo,Qiao, Jiamin,Liu, Junjie,Tian, Miaomiao,Lu, Kui,Zhao, Xia
-
supporting information
(2021/06/15)
-
- Metal-free synthesis of unsymmetrical selenides from pyridinium salts and diselenides catalysed by visible light
-
We report the first metal-free selenolations of pyridinium salts with diselenides to prepare unsymmetrical organoselenides catalysed by visible light. This protocol is an efficient and green method for the preparation of unsymmetrical organoselenides because metal-free conditions and readily accessible diselenides are used.
- Ji, Liangshuo,Qiao, Jiamin,Li, Ankun,Jiang, Zeyi,Lu, Kui,Zhao, Xia
-
supporting information
(2021/05/04)
-
- Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
-
A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.
- Alves, Diego,Sacramento, Manoela Do,Santi, Claudio,Schwab, Ricardo S.,Teixeira, Wystan K. O.,Yano De Albuquerque, Danilo
-
supporting information
(2022/01/12)
-
- An efficient and practical method for the selective synthesis of sodium diselenide and diorganyl diselenides through selenium reduction
-
Studies on an efficient and practical method for the selective synthesis of diorganyl diselenides over diorganyl selenides are presented. Considering the discrepancies between reports on organoselenium compounds, we wanted to establish a tolerable synthetic method for diorganyl diselenides and investigate their characteristics. We optimized reaction conditions for sodium diselenide preparation using selenium, NH2NH2·H2O, and NaOH and, by treating the obtained sodium diselenide with various alkyl or aryl halides, achieved the selective synthesis of diorganyl diselenides in modest to good yields (57–88%) with good reproducibility. We further studied the mechanistic implication, the effects of solvent changes, and the stability of diorganyl diselenides.
- Lim, Yoo Jin,Shin, Na Hye,Kim, Chorong,Kim, Ye Eun,Cho, Hyunsung,Park, Myung-Sook,Lee, Sang Hyup
-
-
- Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes
-
A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy is also applied for kinetic resolution of unsymmetric oxabenzonorbornadiene.
- Li, Sifeng,Yang, Qingjing,Bian, Zhaoxiang,Wang, Jun
-
supporting information
p. 2781 - 2785
(2020/03/30)
-
- Continuous Electrochemical Synthesis of Iso-Coumarin Derivatives from o-(1-Alkynyl) Benzoates under Metal- and Oxidant-Free
-
A non-oxidant and metal-free strategy for synthesizing iso-coumarin by using a continuous electrochemical microreactor to initiate an oxidative cyclization reaction of o-(1-alkynyl) benzoate and radicals. This efficient and clean continuous electrosynthesis method not only avoids the complicated gas protection operation and production of by-products in the batch processes, but also help to overcome the difficulty that batch metal catalysis and electrocatalysis are difficult to scale up, and has the potential for pilot-scale experiment.
- Lin, Xinxin,Fang, Zheng,Zeng, Cuilian,Zhu, Chenlong,Pang, Xinyan,Liu, Chengkou,He, Wei,Duan, Jindian,Qin, Ning,Guo, Kai
-
supporting information
p. 13738 - 13742
(2020/10/02)
-
- Visible-Light-Promoted Selenylative Spirocyclization of Indolyl-ynones toward the Formation of 3-Selenospiroindolenine Anticancer Agents
-
A metal-free and efficient visible-light-induced spirocyclization of indolyl-ynones with diselenides at room temperature under air atmosphere to prepare 3-selenospiroindolenines in moderate to good yields has been developed. The resulting products were tested for in vitro anticancer activity by MTT assay, and compounds 3 c and 3 e showed potent cancer cell-growth inhibition activities.
- Zhou, Xiu-Jie,Liu, Hao-Yang,Mo, Zu-Yu,Ma, Xian-Li,Chen, Yan-Yan,Tang, Hai-Tao,Pan, Ying-Ming,Xu, Yan-Li
-
supporting information
p. 1536 - 1539
(2020/04/20)
-
- Metal-Free ipso -Selenocyanation of Arylboronic Acids Using Malononitrile and Selenium Dioxide
-
The first ipso -selenocyanation of arylboronic acids is achieved using selenium dioxide and malononitrile under mild conditions. The reaction is successful even without metal or base in DMSO. The major advantages of this new method are an easy set-up, excellent yields, and the use of odorless and inexpensive selenium reagents. Basic conditions subsequently afford new access to diaryldiselenides in good yields without isolating the organoselenocyanate intermediates.
- Broggi, Julie,Kosso, Anne Roly Obah,Redon, Sébastien,Vanelle, Patrice
-
p. 3758 - 3764
(2019/09/30)
-
- Metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene: Ortho -quinone methide (VQM)
-
A metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho-quinone methide (VQM) was described herein. The reaction was conducted under mild conditions without any catalysts or additives. Preliminary mechanism studies revealed that the formation of VQM was the key for this alkyne di-functionalization reaction. The reaction could be applied in the enantioselective asymmetric synthesis of axially chiral styrene. Furthermore, the selenosulfonylation adducts can be transformed into useful naphtho[2,1-b]furan and benzofuran scaffolds.
- Huang, Shengli,Chen, Zhili,Mao, Hui,Hu, Fangli,Li, Dongmei,Tan, Yu,Yang, Fengqing,Qin, Wenling
-
supporting information
p. 1121 - 1129
(2019/02/07)
-
- Catalyst-free gem-difunctionalization of fluoroalkyl-substituted diazo compound with diselenide or disulfide and NFSI
-
The gem-difunctionalization of fluoroalkyl-substituted diazo compounds by utilizing diselenides or disulfides and NFSI under catalyst-free and mild conditions is reported. A series of gem-aminoselenolation and gem-aminosulfonylation products bearing fluoroalkyl substituents were obtained in high to excellent yields. Different types of conjugated diazo compounds are also applicable to this transformation. Preliminary mechanistic studies indicate that a selenoimidate intermediate generated from diselenide and NFSI is involved for this transformation.
- Li, Jiuling,Ma, Chaoqun,Xing, Dong,Hu, Wenhao
-
supporting information
p. 2101 - 2105
(2019/03/29)
-
- Rhodium-Catalyzed Carbene Transfer Reactions for Sigmatropic Rearrangement Reactions of Selenium Ylides
-
The rearrangement of selenium ylides is even today almost unexplored, although it would provide access to important organoselenium compounds with broad downstream applications. In this report, the first systematic study of sigmatropic rearrangement reactions of selenium ylides using a simple rhodium catalyst with catalyst loadings as low as 0.01 mol % is described. Selenium oxide pyrolysis of the rearrangement products gives access to important 1,1-disubstituted butadienes.
- Jana, Sripati,Koenigs, Rene M.
-
supporting information
p. 3653 - 3657
(2019/05/24)
-
- Metal-free visible-light induced cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones and diselenides: Access to 5-hydroxy-3-selenyl-4a,8a-dihydro-2: H -chromen-6(5 H)-ones
-
A simple and efficient Se-radical triggered cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones to afford 5-hydroxy-3-selenyl-4a,8a-dihydro-2H-chromen-6(5H)-ones has been developed. This transformation via the 3,5-diselenyl-4a,8a-dihydro-2H-chromen-6(5H)-one intermediate followed by hydrolysis in the presence of CsOAc affords the desired product 3. The resulting products were tested for their in vitro anticancer activity using MTT assay, and compounds 3e and 3q showed potent cancer cell-growth inhibition activities.
- Ma, Xian-Li,Wang, Qian,Feng, Xi-Yuan,Mo, Zu-Yu,Pan, Ying-Ming,Chen, Yan-Yan,Xin, Mao,Xu, Yan-Li
-
supporting information
p. 3547 - 3551
(2019/07/09)
-
- CuO nanoparticles-catalyzed a novel method to the synthesis of symmetrical diselenides from aryl halides: selenoamide as an organic Se-donor reagent
-
A new method is reported for the synthesis of symmetrical diaryldiselenides from aryl halides using selenoamide as an organic Se-donor reagent in the presence of copper (II) oxide nanoparticles. CuO nanoparticles were found to be an efficient and inexpensive catalyst for ligand-free C-Se bond formation with a series of symmetrical diaryldiselenides obtained in good to excellent yield.
- Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh
-
p. 2239 - 2246
(2018/08/04)
-
- Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents
-
A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.
- Cui, Fei-Hu,Chen, Jing,Mo, Zu-Yu,Su, Shi-Xia,Chen, Yan-Yan,Ma, Xian-Li,Tang, Hai-Tao,Wang, Heng-Shan,Pan, Ying-Ming,Xu, Yan-Li
-
supporting information
p. 925 - 929
(2018/02/22)
-
- Regioselective Synthesis of Selenide Ethers through a Decarboxylative Coupling Reaction
-
An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal-free conditions, whereas compounds having two geminal C–Se bonds were formed via the iron(III) chloride/oxygen/cesium carbonate (FeCl3/O2/Cs2CO3) system. Moreover, 1,2-diphenyldisulfane also could be smoothly converted into the corresponding sulfur ether product under the standard reaction conditions. (Figure presented.).
- Cui, Fei-Hu,Chen, Jing,Su, Shi-Xia,Xu, Yan-Li,Wang, Heng-Shan,Pan, Ying-Ming
-
p. 3950 - 3961
(2017/11/20)
-
- The direct synthesis of symmetrical disulfides and diselenides by metal-organic framework MOF-199 as an efficient heterogenous catalyst
-
A highly crystalline porous copper-based metal-organic framework MOF-199 was synthesized, and characterized by several techniques, including XRD, EDX, SEM, and FT-IR. MOF-199 was used as an efficient catalyst for the one-pot and efficient synthesis of organic dichalcogenides from aryl halides (-OTs) and elemental sulfur and selenium in polyethylene glycols (PEGs). A variety of disulfides and diselenides can be obtained in good to excellent yields of up to 98% in a relatively short reaction time.
- Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh
-
p. 87564 - 87570
(2015/11/09)
-
- α-Arylchalcogenation of acetone with diaryl dichalcogenide via metal-free oxidative C(sp3)-H bond functionalization
-
Direct α-arylchalcogenation of acetone with diaryl dichalcogenides has been achieved by using a mixture of TBHP and DTBP oxidants at 120 °C without transition-metal catalyst via oxidative C(sp3)-H bond functionalization. The method exhibits good functional group tolerance and products were isolated in moderate to high yields.
- Yan, Guobing,Borah, Arun Jyoti,Wang, Lianggui,Pan, Zhangjin,Chen, Shuangshuang,Shen, Xuqian,Wu, Xiangmei
-
supporting information
p. 4305 - 4307
(2015/06/22)
-
- Transition-metal free synthesis of diaryl vinyl selenides: A simple synthetic approach with high selectivity
-
A simple, highly efficient synthetic protocol is developed for the synthesis of unsymmetrical diaryl vinyl selenides from diaryldiselenide and β-bromo styrene under transition-metal free conditions in N,N′-dimethyl propylene urea and 130 °C to afford high yields and excellent selectivities. This method provides a new strategy to fabricate a wide variety of important substituted molecular skeletons and an alternative to conventionally used metal salts, additives, and ligands.
- Mohan, Balaji,Hwang, Sori,Woo, Hyunje,Park, Kang Hyun
-
supporting information
p. 2699 - 2702
(2014/04/17)
-
- Efficient silver-catalyzed direct sulfenylation and selenylation of rich arenes
-
An efficient protocol for silver/copper-cocatalyzed direct sulfenylation and selenylation of arenes with aryl disulfides and diselenides has been developed. This strategy exhibits excellent functional group tolerance and high regioselectivity. Mono sulfenylation and selenylation products can be exclusively achieved. This reaction provides a simple and practical route to the preparation of aryl sulfides and selenides. This journal is
- Yan, Guobing,Borah, Arun Jyoti,Wang, Lianggui
-
supporting information
p. 9557 - 9561
(2015/02/19)
-
- Copper-catalyzed chalcogenation of aryl iodides via reduction of chalcogen elements by aluminum or magnesium
-
Aluminum-induced copper-catalyzed coupling of aryl iodides with selenium or sulfur element could afford the corresponding diaryl selenides or sulfides in good yields. When magnesium chloride as an additive was employed, diaryl monoselenides and monosulfides were selectively obtained. On the contrary, the use of sodium carbonate produced diaryl diselenides and disulfides. The preparation of diaryl diselenides was necessary for magnesium as a reductant. Regrettably, tellurium was very low reactivity.
- Taniguchi, Nobukazu
-
p. 10510 - 10515,6
(2012/12/12)
-
- An efficient one-pot synthesis of symmetrical diselenides or ditellurides from halides with CuO nanopowder/Se0 or Te0/base
-
(Equation Presented). A CuO nanopowder-catalyzed coupling reaction of aryl, alkyl, and heteroaryl iodides with elemental selenium and tellurium takes place in the presence of KOH at 90 °C in DMSO. A wide range of substituted symmetrical diselenides and ditellurides were afforded with good to excellent yields.
- Singh, Devender,Deobald, Anna M.,Camargo, Leandro R.S.,Tabarelli, Greice,Rodrigues, Oscar E.D.,Braga, Antonio L.
-
supporting information; experimental part
p. 3288 - 3291
(2010/09/30)
-
- Oxidation of α-sulfonyl selenides: Formation of selenolesters
-
Treatment of 7-phenylseleno-7,12-dihydrobenzo[5,6][1,3]thiazepino[3,2-a]benzimidazole 6,6-dioxide 7a in CH2Cl2 with m-chloroperbenzoic acid (MCPBA) and 28% H2O2 at room temperature gave Se-phenyl 2-[(benzimidazol-l-yl)methyl]selenobenzoate 8a. Similarly, the oxidation of sulfone 7a in THF with aqueous Oxone7 at room temperature gave the same selenolester 8a. The formation of selenolesters 8 can be explained by assuming either the involvement of oxaseleniranium cation 13, having a sulfinate group at C-2 of the benzimidazole moiety, as an intermediate which is believed to be formed by an intramolecular nucleophilic attack of the polarized oxygen of the Se=O bond of selenoxide 6 to the α-carbon next to the sulfonyl group, or Pummerer-type reactions.
- Yi, Jae Sang,Kim, Kyongtae
-
-
- Di(phenylsulfonyl) diselenide (PhSO2Se)2 and phenylsulfonylselenyl chloride (PhSO2SeCl) as new selenium-transfer reagents in the synthesis of functionalised diselenides and selenides
-
The title electrophilic selenium reagents have been used to synthesise functionalised diselenides and selenides.
- Chesney,Bryce,Cooke
-
p. 1521 - 1524
(2007/10/02)
-
- Samarium diiodide-induced reduction of amorphous selenium: A facile synthesis of diaryl diselenides
-
Samarium diiodide reduces amorphous selenium to Se2/2- in THF. Subsequent addition of aryldiazonium fluoborates affords diaryl diselenides in moderate to good yields.
- Zhang,Jia,Zhou
-
p. 1247 - 1252
(2007/10/02)
-
- STUDIES ON LONG-RANGE COUPLINGS BETWEEN 77Se AND 13C IN SOME ARYL SELENIDES, DICHLORIDES, AND SELENOXIDES. THE INVERSE EFFECT ON COUPLINGS IN THE SELENOXIDE FORMATION.
-
Long-range coupling constants between **7**7Se and **1**3C in selenoanisole, diphenyl selenide, diphenyl diselenide, and their 2-mono- and 2,2 prime -disubstituted derivatives, selenoxanthone, selenanthrene, dichlorides, and selenoxides were measured to disclose predominant factors governing the magnitude of the coupling. Extraordinary large values for two- and three-bond couplings are found in selenoxanthone. Three factors are operative: the orientational effect, the coordination number, and the effect of ring formation. The last factor accompanies a stronger inverse effect on the coupling of selenoxides than on that of selenides.
- Nakanishi,Ikeda
-
p. 1661 - 1664
(2007/10/02)
-