- An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions
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An efficient protocol to synthesize aryl selenoethers through deborylative selenylation of widely available arylboronic acids has been established under electrochemical conditions in the absence of metal catalyst and external oxidant. The synthesis of bio
- Cai, Hu,Fu, Zhengjiang,Guo, Shengmei,He, Dongdong,Yi, Xuezheng,Yin, Jian
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supporting information
p. 130 - 135
(2022/01/19)
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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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- Combination of Lewis Basic Selenium Catalysis and Redox Selenium Chemistry: Synthesis of Trifluoromethylthiolated Tertiary Alcohols with Alkenes
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A new and efficient method for diaryl selenide catalyzed vicinal CF3S hydroxylation of 1,1-multisubstitued alkenes has been developed. Various trifluoromethylthiolated tertiary alcohols could be readily synthesized under mild conditions. This method is also effective for the intramolecular cyclization of alkenes tethered by carboxylic acid, hydroxy, sulfamide, or ester groups and is associated with the introduction of a CF3S group. Mechanistic studies have revealed that the pathway involves a redox cycle between Se(II) and Se(IV) and Lewis basic selenium catalysis.
- Zhu, Zechen,Luo, Jie,Zhao, Xiaodan
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supporting information
p. 4940 - 4943
(2017/09/23)
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- Simple and efficient copper-catalyzed synthesis of symmetrical diaryl selenides from triarylbismuthanes and selenium under aerobic conditions
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Symmetrical diaryl selenides were synthesized in moderate-to-excellent yields by Cu-catalyzed C(aryl)–Se bond formation followed by the reaction of triarylbismuthanes with elemental Se in the presence of Cu(OAc)2 and 1,10-phenanthroline (10 mol%) under aerobic conditions. This reaction proceeded efficiently: All the aryl groups on Bi were transferred to the coupling products.
- Matsumura, Mio,Kumagai, Hanae,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
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- Organoselenium and DMAP co-catalysis: Regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes
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A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. 77Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.
- Verma, Ajay,Jana, Sadhan,Prasad, Ch. Durga,Yadav, Abhimanyu,Kumar, Sangit
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supporting information
p. 4179 - 4182
(2016/03/19)
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- Metal free synthesis of diaryl selenides using SeO2as a selenium source
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A simple, efficient, and eco-friendly synthetic protocol has been developed for the preparation of diaryl selenium compounds. To the best of our knowledge, this is the first Letter on the use of selenium dioxide as selenium source for the synthesis of diaryl selenides. Compared with other selenium sources the new source SeO2gives an environment-friendly and low-cost synthetic route, which may be useful for large-scale synthesis.
- Kumar, R. Uday,Reddy, K. Harsha Vardhan,Satish,Swapna,Nageswar
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supporting information
p. 4138 - 4141
(2016/08/24)
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- Diarylation of chalcogen elements using arylboronic acids via copper- or palladium-catalyzed oxidative coupling
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Transition metal-catalyzed diarylations of sulfur, selenium and tellurium were achieved using arylboronic acids in air. A copper-catalyzed reaction of sulfur or selenium efficiently yielded numerous symmetrical diaryl sulfides or selenides in the presence of NH4BF4. However, the diarylation of tellurium was not possible using this method, and required a palladium catalyst in the presence of KI and air for the reaction to proceed.
- Taniguchi, Nobukazu
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p. 5818 - 5823
(2016/08/30)
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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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- Synthesis of 9-oxoselenoxanthenium and triarylselenonium hexafluorophosphates
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The selenoxides forming 9-oxoselenoxanthenium and triaryl selenonium hexafluorophosphates via interaction with heptyl phenyl ether and anisole in the MeSO3H-P2O5 mixture followed by treatment with KPF6 have been obtained via selenoxantene-9-one and diphenyl selenide derivatives oxidation with m-chloroperoxybenzoic acid or hydrogen peroxide.
- Loskutov,Balina,Russkikh,Shelkovnikov
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p. 1093 - 1097
(2015/06/30)
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- 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
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supporting information
p. 1057 - 1061
(2014/02/14)
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- 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
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supporting information
p. 1057 - 1061
(2015/02/19)
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- The Chan-Lam reaction of chalcogen elements leading to aryl chalcogenides
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A copper-catalyzed chalcogenation of arylboronic acids with elemental sulfur or selenium is established, which provides diaryl disulfides or diaryl monoselenides in moderate to good yields with excellent selectivities, respectively. Moreover, after sequential reduction and coupling with aryl/alkyl iodides in one pot, unsymmetrical monosulfides were obtained in good yields.
- Yu, Jin-Tao,Guo, Huan,Yi, Yuanqiuqiang,Fei, Haiyang,Jiang, Yan
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supporting information
p. 749 - 752
(2014/04/03)
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- An efficient one-pot approach to selenides: CuI-catalyzed reactions of magnesium selenolate with aryl or alkyl halides
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An efficient one-pot route to symmetrical selenides in GC with yields from 13 to 94% has been developed by CuI catalyzing reactions of magnesium organoselenolates with aryl or alkyl halides under mild conditions. It is suggested that selenium could leave from PhSeMgBr to form other RSeMgBr with RMgBr based on experimental results. Although the leaving selenium causes low yield of unsymmetrical selenides and complex products, it offers a slowly releasing selenium source in preparation of nano metal selenides, and a potential leaving group in nucleophilic substitution. The role of excess magnesium is proposed.
- Gao, Fei,Tang, Yu,Lin, Hemei,Yang, Jun,Zhang, Yuanming
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p. 787 - 793
(2013/07/26)
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- Synthesis and evaluation of diaryl sulfides and diaryl selenide compounds for antitubulin and cytotoxic activity
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We have devised a procedure for the synthesis of analogs of combretastatin A-4 (CA-4) containing sulfur and selenium atoms as spacer groups between the aromatic rings. CA-4 is well known for its potent activity as an inhibitor of tubulin polymerization, a
- Dos Santos, Edson Dos A.,Hamel, Ernest,Bai, Ruoli,Burnett, James C.,Tozatti, Camila Santos Suniga,Bogo, Danielle,Perdomo, Renata T.,Antunes, Alexandra M.M.,Marques, M. Matilde,Matos, Maria De F.C.,De Lima, Dênis P.
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supporting information
p. 4669 - 4673
(2013/08/23)
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- Microwave-assisted Cu2O-catalyzed one-pot synthesis of symmetrical diaryl selenides from elemental selenium
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A novel and simple microwave-assisted one-pot protocol to prepare symmetrical diaryl selenides has been developed. A cross-coupling reaction between aryl iodide and elemental selenium takes place in the presence of KOH and a catalytic amount of Cu2O/NH2CH2CH 2NH2, leading to C-Se bond formation. The reactions are highly efficient with a reaction time of 1 h under microwave irradiation and yields from 50% to 90%.
- Zhang, Shaozhong,Karra, Kranthi,Heintz, Christina,Kleckler, Erica,Jin, Jin
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supporting information
p. 4753 - 4755
(2013/08/23)
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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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- Copper-catalyzed chalcogenation of aryl iodides via reduction of chalcogen elements by aluminum or magnesium
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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
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p. 10510 - 10515,6
(2012/12/12)
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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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- Synthesis of arylselenide ethers by photoinduced reactions of selenobenzamide, selenourea and selenocyanate anions with aryl halides
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Selenobenzamide (-SeCNH(Ph), 1), selenourea ( -SeCNH(NH2), 2) and selenocyanate (-SeCN, 3) anions afford areneselenolate ions (ArSe-) under photostimulation in the presence of tert-butoxide or 2-naphthoxide ions as electron donors (entrainment conditions) in DMSO. In a 'one-pot' procedure, ArSe- anions can be trapped by a subsequent aliphatic nucleophilic substitution giving aryl methyl selenides in good to excellent yields (67-100%). This simple approach is compatible with electron-donating and electron-withdrawing substituents, such as nitro and carbonyl groups.
- Bouchet, Lydia M.,Pe?é?ory, Alicia B.,Argüello, Juan E.
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experimental part
p. 969 - 972
(2011/03/20)
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- Nano copper oxide catalyzed synthesis of symmetrical diaryl selenides via cascade reaction of KSeCN with aryl halides
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An unprecedented transfer of selenium ion from potassium selenocyanate was observed in C-Se cross-coupling reaction catalyzed by copper oxide nanoparticles under ligand-free conditions. Utilizing this protocol wide range of symmetrical diaryl selenides were obtained in excellent yields. Nano-CuO is recyclable up to four cycles without loss of catalytic activity. Georg Thieme Verlag Stuttgart · New York.
- Reddy, K. Harsha Vardhan,Reddy, V. Prakash,Madhav,Shankar,Nageswar
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supporting information; experimental part
p. 1268 - 1272
(2011/07/06)
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- Potassium selenocyanate as an efficient selenium source in C-Se cross-coupling catalyzed by copper iodide in water
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An efficient and conceptually new protocol for C-Se cross coupling of potassium selenocyanate with aryl halides via copper-catalyzed cascade reaction has been developed in water. Utilizing this protocol, a variety of aryl and heteroaryl halides were reacted with potassium selenocyanate to afford the corresponding diaryl selenides in moderate to good yields.
- Kumar, A. Vijay,Reddy, V. Prakash,Reddy, C. Suresh,Rao, K. Rama
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supporting information; experimental part
p. 3978 - 3981
(2011/08/09)
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- Unexpected C-Se cross-coupling reaction: Copper oxide catalyzed synthesis of symmetrical diaryl selenides via cascade reaction of selenourea with aryl halides/boronic acids
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Selenourea is used as an effective selenium surrogate in the C-Se cross-coupling reaction catalyzed by copper oxide nanoparticles under ligand free conditions. This protocol has been utilized for the synthesis of a variety of symmetrical diaryl selenides in good to excellent yields from the readily available aryl halides/boronic acids.
- Reddy, V. Prakash,Kumar, A. Vijay,Rao, K. Rama
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scheme or table
p. 8720 - 8723
(2011/03/19)
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- CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids
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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.
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scheme or table
p. 6635 - 6638
(2010/03/01)
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- Deoxygenation of sulfoxides, selenoxides, telluroxides, sulfones, selenones and tellurones with Mg-MeOH
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The deoxygenation of a variety of sulfoxides, selenoxides, telluroxides, sulfones, selenones and tellurones has been reported with Mg-MeOH at room temperature in nearly quantitative yields. The deoxygenation is proposed to proceed by SET from Mg to the substrate.
- Khurana, Jitender M.,Sharma, Vandana,Chacko, Silvi A.
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p. 966 - 969
(2007/10/03)
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- Mono- or dichalcogenation of aryl iodide with sulfur or selenium by copper catalyst and aluminum
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The copper-catalyzed mono- or dichalcogenation of aryl halide with sulfur or selenium can be carried out with the addition of aluminum. This method takes advantage of two properties of both the insertion of copper into the chalcogen-chalcogen bond and the reductive ability of aluminum. Furthermore, the addition of MgCl2 or Na2CO3 enables the selective synthesis of diaryl monochalcogenides or disulfides. Georg Thieme Verlag Stuttgart.
- Taniguchi, Nobukazu
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p. 1687 - 1690
(2007/10/03)
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- Selective deoxygenation of aryl selenoxides by triaryl phosphites. Evidence for a concerted transformation
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Triaryl phosphites selectively reduce aryl selenoxides to selenides. The Hammett plot of the reactions of para-phenyl substituted triaryl phosphites with diphenyl selenoxide gave ρ=+2.3, whereas with bis(p-methoxyphenyl) selenoxide, ρ=-2.1. The results are consistent with a concerted mechanism for the oxygen transfer from Se to P.
- Stratakis, Manolis,Rabalakos, Constantinos,Sofikiti, Nikoletta
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p. 349 - 351
(2007/10/03)
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- Mild reduction of tellurium(IV) and selenium(IV) compounds by sodium ascorbate
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Sodium ascorbate was found to mildly reduce organyltellurium trihalides to diorganyl ditellurides, organylselenium trihalides to diorganyl diselenides, diorganyltellurium dihalides and oxides to diorganyl tellurides and diorganylselenium dihalides and oxides to diorganyl selenides.
- Engman,Persson
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p. 445 - 458
(2007/10/02)
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- A convenient method for the preparation of diaryl tellurides and diaryl selenides
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Sodium hydrogen telluride or selenide reacts rapidly with aryldiazonium fluoborates to give the corresponding symmetric diaryl tellurides or selenides.
- Chen,Qiu,Zhou
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p. 1729 - 1734
(2007/10/02)
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- A new route to seleno and telluro esters by Co2(CO)8-mediated and -catalyzed carbonylation of diaryl diselenides and ditellurides with carbon monoxide
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Diaryl Diselenides react with CO(5-100 atm) at 100-200°C during 1-4 h in the presence of Co2(CO)8 to give the corresponding aryl selenocarboxylic acid esters in 21-96% yields. Similar treatment of diphenyl ditelluride gives the telluro analogues in lower yields. Didodecyl diselenide also gives the corresponding seleno ester, while esters were not produced from dibenzyl diselenide and didodecyl ditelluride. Under milder conditions (10 atm CO/125°C/1 h) the reactivity of (PhM)2 (M S, Se, Te) for the corresponding esters was found to be in the order Te > Se > S. The carbonylation of diaryl diselenides proceeds catalytically in Co2(CO)8 in the presence of triphenylphosphine. It was shown unambiguously that benzoylcobalt tetracarbonyl, which is one of the possible intermediates when aryl is phenyl, reacts smoothly with diphenyl diselenide or ditellutide to give the corresponding ester, phenyl selenobenzoate or tellurobenzoate, respectively, in a good yield.
- Uemura, Sakae,Takahashi, Hidetaka,Ohe, Kouichi,Sugita, Nobuyuki
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- Relative Reactivities of Nucleophiles Derived from Group 6A toward Aryl Radicals
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Competition experiments have been carried out in liquid ammonia at reflux temperature to determine the relative rate constants for the coupling reactions of nucleophiles derived from group 6A of the periodic table toward aryl radicals.The nucleophiles studied were of type PhZ- (Z=S, Se, Te).It has been proposed that these nucleophiles react under photochemical stimulation with haloaromatic substrates through the SRN1 mechanism of aromatic substitution.The experimental results suggest that the coupling reaction aryl radical-PhZ- anion can be reversible or irreversible depending on the nature of the aryl moiety and the PhZ- nucleophile.Relative rate constants have been determined under conditions of irreversible coupling of the nucleophiles PhZ- (Z=S, Se, Te) with 2-quinolyl radicals.Results here reported indicate an increasing reactivity as we go down the group: PhO- (0.0), PhS- (1.00), PhSe- (5.8), PhTe- (28).The relative rate constant when one of the coupling reactions is reversible supports our mechanistic suggestions.
- Pierini, Adriana B.,Penenory, Alicia B.,Rossi, Roberto A.
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p. 486 - 490
(2007/10/02)
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- APPLICATION OF BIS(p-METHOXYPHENYL)SELENOXIDE AS AN OXIDIZING AGENT OF KORNBLUM OXIDATION
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The title selenoxide was found to serve as a suitable agent for Kornblum oxidations of various benzyl bromides to the corresponding carbonyl compounds.On the other hand, the analogous sulfoxide and telluroxide hardly promoted such oxidations.
- Ariyoshi, Kimio,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
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p. 891 - 892
(2007/10/02)
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