- Palladium Complex Immobilized on Magnetic Nanoparticles Modified with 2-Aminopyridine Ligand: A Novel and Efficient Recoverable Nanocatalyst for C–S and C–Se Coupling Reactions
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A novel, versatile and efficient magnetically recoverable palladium nanocatalyst [Fe3O4@SiO2/2-aminopyridine-Pd(II)] was fabricated via the immobilization of palladium(II) complex on the surface of magnetic nanoparticles modified with 2-aminopyridine ligand. The structure of the as-fabricated Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was characterized by a series of spectroscopic techniques including FT-IR, SEM, TEM, EDX, TGA, XRD, VSM and ICP-OES techniques. The Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was utilized under mild and eco-friendly conditions in C–S and C–Se coupling reactions to afford a vast variety of diaryl sulfides and diaryl selenides with good to excellent yields. This heterogeneous palladium catalyst can be magnetically separated and reused for at least 7 consecutive trials without any reduction in activity. Graphical Abstract: [Figure not available: see fulltext.]
- Lu, Lu,Luo, Jia,Wang, Weiqi,Xu, Xiaoqing,Zhang, Jingzheng
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- Trichloroisocyanuric Acid-Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature
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A transition-metal-free method for the synthesis of arylselenides and aryltellurides has been established based on the oxidative cross-coupling between diorganyl dichalcogenides and aryl boronic acids. With trichloroisocyanuric acid as an oxidant, the reaction proceeded smoothly to afford the desired products in 45–97% yields at ambient temperature. Three reaction reagents used in this method are stoichiometric and the oxidation by-product isocyanuric acid can be easily isolated and recovered. Besides of arylboronic acids, aryl trifluoroborates and aryl trihydroxyborates salts are also able to perform this transformation. (Figure presented.).
- Sun, Nan,Zheng, Kai,Sun, Pengyuan,Chen, Yang,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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p. 3577 - 3584
(2021/06/15)
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- Ni nanoparticle-confined covalent organic polymer directed diaryl-selenides synthesis
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The present work describes the preparation of a new covalent organic polymer (COP) and its application as a hetero support for diaryl selenides synthesis. A nitrogen rich COP (CGP) has been synthesized via SNAr reaction of cyanuric chloride with guanidinium hydrochloride. The successful confinement of COP with Ni nanoparticles through post-synthetic transformations (Ni?CGP) provides excellent catalytic activity for the transformation of aryl halides into diaryl selenides using elemental selenium powder. The synthetic transformations are well confirmed using various modern analytical and spectroscopic techniques which reveal high chemical and thermal durability. The N-rich framework of CGP fortifies the confinement of Ni NPs. Ni?CGP provides an efficient approach for diaryl selenides synthesis using a very cheap selenating reagent under water benign solvent conditions (DMSO?:?H2O) at room temperature with high reusability. Significantly, our work not only contributes the opportunity for developing economical and effective non-noble metal decorated COPs as heterogeneous catalysts, but also delivers an efficient approach to produce industrially important C-Se coupling products.
- Awasthi, Satish Kumar,Dixit, A. K.,Raghothama, S.,Yadav, Deepika
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supporting information
p. 12266 - 12272
(2020/10/02)
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- Selenium dioxide promoted dinitrogen extrusion/direct selenation of arylhydrazines and anilines
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A novel, efficient, economical strategy for the coupling and direct selenation of arylhydrazines to selenides using SeO2 has been developed. Our method employs SeO2 as the selenium source with hydrazines as coupling reactants to generate selenides via dinitrogen extrusion. This reagent also helped to generate ArSe substitued aniline derivatives via C–H functionalization reaction in good yields. The application of this method in gram scale was also carried out.
- Yaqoob Bhat, Mohammad,Kumar, Atul,Naveed Ahmed, Qazi
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supporting information
(2020/03/19)
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- Method for preparing asymmetric organic selenium ether compounds through metal-free chemical oxidation method (by machine translation)
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The method is mild in reaction condition, convenient to operate, high in 1 reaction condition, convenient 2 to operate, high in safety, wide in substrate range, high 2 - 8h in yield, particularly suitable for reaction of various poor 3 electric and sterically hindered arylboronic acid and diselenoxy ether, and capable of finishing most of the reaction 4h. (by machine translation)
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Paragraph 0059-0062; 0064
(2020/12/09)
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- Selenacalix[4]dithienothiophene: Synthesis, Structure, and Complexation of a Cyclic Tetramer of Selenide-Bridging Dithienothiophene
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An efficient cyclization toward a cyclic tetramer of dithienothiophene (DTT) linked by divalent selenium atoms has been developed via palladium-catalyzed coupling reaction of (nBu3Sn)2Se. X-ray analysis revealed its highly symmetrical structure had an alternate arrangement of DTT units. There are several Se???π interactions forming a supramolecular network leading to large void channel space. The cyclic tetramer possesses moderate electron-donating ability. Furthermore, the cyclic tetramer undergoes complexation with C60 in a 1:2 ratio in the solid state to give a highly symmetrical three-dimensional array of C60.
- Hasegawa, Masashi,Takahashi, Kazuhiro,Inoue, Ryota,Haga, Shiori,Mazaki, Yasuhiro
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supporting information
p. 1647 - 1650
(2018/09/21)
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- Palladium Nanoparticles Supported on Nitrogen-rich Containing Melamine-based Microporous Covalent Triazine Polymers as Efficient Heterogeneous Catalyst for C?Se Coupling Reactions
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In the present work, microporous nitrogen containing covalent triazine polymers (CTPs) TATAM was synthesized from condensation of 4,4′4′′-(1,3,5-triazine-2,4,6-triyl) tribenzaldehyde (TATA) and melamine under solvothermal conditions to obtain nitrogen- rich triazine containing polymeric supported materials (TATAM). Further, palladium nanoparticles (Pd NPs) were supported on TATAM polymeric networks (Pd@TATAM). The synthesized Pd@TATAM CTPs material was thoroughly characterized by FT-IR, UV-DRS, solid state 13C-CPMAS, XPS, powder X-ray diffraction, TGA, SEM, TEM. In addition, the characterized Pd@TATAM CTPs were applied to check the catalytic application. The Pd@TATAM was shown to be an efficient and reusable heterogeneous solid catalyst for the formation of C?Se bond through coupling of aryl halide and elemental selenium, dimethyl sulfoxide as a solvent at 100 °C for about 6 h. Besides the absence of metal leaching for catalytic system, it is also observed that the catalyst can be reused for three consecutive cycles with a minimal decrease in its activity.
- Sadhasivam, Velu,Balasaravanan, Rajendiran,Chithiraikumar, Chinnadurai,Siva, Ayyanar
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p. 3833 - 3844
(2018/07/30)
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- MANUFACTURING METHOD OF ARYL COMPOUND
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PROBLEM TO BE SOLVED: To provide a manufacturing method of an aryl compound capable of a coupling reaction using an organic halide having any aromatic cyclic group. SOLUTION: There is provided a manufacturing method of an aryl compound for a cross-couplin
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Paragraph 0046-0047
(2017/09/23)
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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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- 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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- 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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- Transition-metal free synthesis of diaryl vinyl selenides: A simple synthetic approach with high selectivity
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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
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p. 2699 - 2702
(2014/04/17)
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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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- A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
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A simple and convenient approach for the synthesis of unsymmetrical diaryl chalcogenides (Te, Se, and S) has been developed by copper-catalyzed cross-coupling reaction of organoboronic acid with diaryl dichalcogenide in ethanol using NaBH4 in air or oxygen. The present methodology is highly practical for the synthesis of unsymmetrical diaryl tellurides with various functionalities such as -NO2, -F, -Br, and -COOH that have been obtained in good to excellent yields. Methodology is also effective for the synthesis of unsymmetrical diaryl selenides and sulfides. Moreover, symmetrical diaryl selenides have also been obtained from arylboronic acids using elemental selenium powder under optimized reaction conditions. The use of NaBH 4 is the key for the development of milder reaction conditions, which enable the construction of unsymmetrical diaryl chalcogenides from boronic acid substrates in ethanol at room temperature.
- Kumar, Amit,Kumar, Sangit
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p. 1763 - 1772
(2014/03/21)
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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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- 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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- 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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- A novel and efficient synthesis of selenides
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Under nitrogen atmosphere, a simple and efficient procedure for the synthesis of symmetrical selenides has been developed by the reaction of aryl or alkyl halides with magnesium (1.5 equiv) and elemental selenium (1.0 equiv) in the absence of catalyst and ligand in THF and toluene under reflux at 86°C. This protocol has been utilized for the synthesis of a variety of symmetrical selenides in good to excellent yields. ARKAT-USA, Inc.
- Lin, He M.,Tang, Yu,Li, Zhi H.,Liu, Kun D.,Yang, Jun,Zhang, Yuan M.
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experimental part
p. 146 - 156
(2012/09/21)
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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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- A highly efficient method for the copper-catalyzed selective synthesis of diaryl chalcogenides from easily available chalcogen sources
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An efficient protocol for copper-catalyzed C-S or C-Se bond formation between aryl iodides and easily available chalcogen sources leading to diaryl chalcogenides is reported. A variety of symmetrical diaryl sulfides and diaryl selenides were synthesized in good to excellent yields. Unsymmetrical diaryl sulfides were also obtained in moderate yields from two different aryl iodides by a one-pot tandem process. This strategy was further successfully utilized for the synthesis of 2-phenylbenzo[b]thiophene and of [1]benzothieno[3,2-b] benzothiophene. A new Cu-catalyzed one-pot approach for the selective synthesis of symmetrical diaryl chalcogenides and unsymmetrical diarylsulfides with use of Na2S or Se as chalcogen sources has been developed. Copyright
- Li, Yaming,Nie, Caiping,Wang, Huifeng,Li, Xiaoying,Verpoort, Francis,Duan, Chunying
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experimental part
p. 7331 - 7338
(2012/01/06)
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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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- 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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- The first aryne evolution from the reactions of selenonium salts with aryllithiums
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The first example of the benzyne generation was found in the reactions of alkynylselenonium salt 1a with 1.0 equiv. of phenyllithium in THF at room temperature for 3 h. The formation of the aryne intermediate was confirmed in the reactions of alkynylselenonium salt 1b and tri-p-tolylselenonium salt 6b with tolyllithium, which gave a mixture of alkynylbiphenyl derivatives 18 and 19 in 19% yield (18:19=11:8) and a mixture of bitolyls 28 and 29 in 63% yield (28:29=2:1), respectively. The reaction mechanisms of these reactions are discussed. (C) 2000 Elsevier Science Ltd.
- Watanabe, Shin-Ichi,Yamamoto, Keiichirou,Itagaki, Yukiko,Iwamura, Tatsunori,Iwama, Tetsuo,Kataoka, Tadashi
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p. 855 - 863
(2007/10/03)
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- Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides: First Isolation of Oxyselenuranes [10-Se-4(C3O)] as a Reaction Intermediate
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The reaction of the diphenyl(phenylethynyl)selenonium triflate 1a with active methylene compounds 5 and t-BuOK in THF gave furan derivatives 6. The [10-Se-4(C3O)l selenuranes 8a and 8b could be isolated from the reactions with benzoylacetonitrile 5f and with 1,3-indandione 5g, respectively, as reaction intermediates. The structures of the selenuranes 8 were elucidated by X-ray crystallography and 77Se high-resolution solid-state NMR spectroscopy. The selenuranes 8 underwent ligand coupling on standing at room temperature or refluxing in chloroform and gave the furan derivatives 6 and the ring-opened product 9. Similarly, the reaction of 1a with benzamide 13a and pivalamide 13d in the presence of NaH in THF afforded oxazole derivatives 14.
- Kataoka, Tadashi,Watanabe, Shin-Ichi,Yamamoto, Keiichirou,Yoshimatsu, Mitsuhiro,Tanabe, Genzoh,Muraoka, Osamu
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p. 6382 - 6386
(2007/10/03)
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- ORGANOSELENIUM COMPOUNDS VII. METHODS OF CONTROLLING THE REACTION OF ORGANIC HALIDES WITH MAGNESIUM AND SELENIUM
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The action of aryl bromides on a mixture of magnesium and selenium in ether in ratios of 1.5-2:1:1 leads to diaryl selenides and bis(bromomagnesium) selenide, which gives organic selenides with electrophiles.The reaction of Grignard reagents with an excess of selenium (ArBr:Mg:Se ratios of 1:1:1.5) in ether leads to diaryl diselenides, while the reaction in THF leads to a mixture of polyselenides and diaryl diselenides.
- Nedugov, A. N.,Pavlova, N. N.,Lapkin, I. I.
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p. 1829 - 1832
(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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