80461-61-6Relevant academic research and scientific papers
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
Lu, Lu,Luo, Jia,Wang, Weiqi,Xu, Xiaoqing,Zhang, Jingzheng
, (2022/01/12)
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.]
An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions
Cai, Hu,Fu, Zhengjiang,Guo, Shengmei,He, Dongdong,Yi, Xuezheng,Yin, Jian
supporting information, p. 130 - 135 (2022/01/19)
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
Arylseleninic acid as a green, bench-stable selenylating agent: Synthesis of selanylanilines and 3-selanylindoles
Abenante, Laura,Anghinoni, Jo?o M.,Lenard?o, Eder J.,Padilha, Nathalia B.,Penteado, Filipe,Rosati, Ornelio,Santi, Claudio,Silva, Marcio S.
, p. 5210 - 5217 (2020/07/23)
Arylseleninic acids were used as an electrophilic selenium source in aromatic substitution reactions, using N,N-substituted anilines and indoles as nucleophiles at 70 °C for 6-15 h. A total of fourteen 4-selanylanilines and five 3-selanylindoles were selectively obtained in good to excellent yields. The starting benzeneseleninic acids are easily prepared from the respective diselenides, are bench stable and easy to handle, affording water as the only waste at the end of the reaction. This journal is
Electrochemical Oxidative C(sp2)–H Bond Selenylation of Activated Arenes
Meirinho, Anne G.,Pereira, Vinícius F.,Martins, Guilherme M.,Saba, Sumbal,Rafique, Jamal,Braga, Antonio L.,Mendes, Samuel R.
supporting information, p. 6465 - 6469 (2019/08/21)
Herein, we report an electrochemical oxidative C(sp2)–H selenylation of activated arenes. The reaction proceeds in an undivided electrochemical cell at Pt-electrodes in the presence of KI as the supporting electrolyte, which could suffer oxidat
Visible-light-induced metal and reagent-free oxidative coupling of: Sp 2 C-H bonds with organo-dichalcogenides: Synthesis of 3-organochalcogenyl indoles
Rathore, Vandana,Kumar, Sangit
supporting information, p. 2670 - 2676 (2019/06/03)
Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C-H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone at room temperature. This benign protocol allows one to access a wide range of 3-arylselenylindoles, 3-arylthioindoles and even 3-aryltelluroindoles with good to excellent yields. Various functionalities namely, methoxy, and halo either on indoles or aryl dichalcogenides showed amenability to the developed reaction. Furthermore, thiocyanation of the sp2 C-H bonds of indoles has been accomplished by this visible light induced method. A mechanistic understanding by UV-visible, EPR spectroscopy, and cyclic voltammetry suggests that light induces electron transfer from the electron rich arene to oxygen providing an arene radical cation and a superoxide radical anion. Subsequently, reaction of the radical cation with aryl dichalcogenides provides a diaryl chalcogenyl cation which upon removal of protons gave unsymmetrical 3-indolyl aryl chalcogenides.
Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light
Lemir, Ignacio D.,Castro-Godoy, Willber D.,Heredia, Adrián A.,Schmidt, Luciana C.,Argüello, Juan E.
, p. 22685 - 22694 (2019/08/01)
A novel and sustainable procedure was developed for the synthesis of 3-selenylindoles employing diorganyl diselenides and indoles or electron-rich arenes as starting materials. Visible blue light was used to promote the reaction without employing transiti
A simple method for the preparation of arylselanyl anilines
Zhou, Zhongshi,He, Xuehan
supporting information, p. 2553 - 2558 (2018/10/24)
In the presence of I2, a simple method for the preparation of arylselanyl anilines from anilines and diselenides is developed. This metal-free iodine-promoted procedure proceeds efficiently under mild reaction conditions, providing a series of
Rose Bengal catalysed photo-induced selenylation of indoles, imidazoles and arenes: A metal free approach
Saba, Sumbal,Rafique, Jamal,Franco, Marcelo S.,Schneider, Alex R.,Espíndola, Leandro,Silva, Dagoberto O.,Braga, Antonio L.
supporting information, p. 880 - 885 (2018/02/19)
In this report, the highly efficient Rose Bengal-catalysed C(sp2)-H selenylation of indoles, imidazoles and arenes was achieved using a half molar equiv. of diorganoyl diselenides. This metal-free, photo-induced protocol resulted in selenylated
Efficient heterogeneous copper-catalysed C–Se coupling of aryl iodides with symmetrical diselenides towards unsymmetrical monoselenides
Zhao, Ruonan,Yan, Chenyu,Jiang, Yuanyuan,Cai, Mingzhong
, p. 584 - 588 (2018/11/27)
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.
Synthesis of Diaryl Selenides via Palladium-Catalyzed Debenzylative Cross-Coupling of Aryl Benzyl Selenides with Aryl Bromides
Wang, Hao,Chen, Shuguang,Liu, Guoqing,Guan, Haixing,Zhong, Daoyin,Cai, Jun,Zheng, Zhipeng,Mao, Jianyou,Walsh, Patrick J.
supporting information, p. 4086 - 4091 (2018/11/21)
Herein, we report a novel method for synthesizing diaryl selenides from aryl benzyl selenides and aryl bromides via debenzylative cross-coupling with a Pd/NIXANTPHOS-catalyst. NIXANTPHOS outperformed other commonly used bi- and monodentate ligands examined in this novel transformation. This reaction system displays wide functional group tolerance and excellent substrate scope. The transformation broadens the scope of palladium-catalyzed debenzylative processes to use selenolate anions as a leaving group. Its potential for practical synthetic applications was demonstrated with the gram scale synthesis of 4-chlorophenyl phenyl selenide.
