16089-79-5Relevant academic research and scientific papers
Development of a selenide-based fluorescent probe for imaging hypochlorous acid in lysosomes
Qu, Zongjin,Ding, Junxia,Zhao, Meiyu,Li, Peng
, p. 1 - 8 (2015)
The development of fluorescent probes for hypochlorous acid (HOCl) has received intense attention because of the biological significance of HOCl. In this work, a novel fluorescent probe based on a selenide switch for the detection of HOCl in lysosomes has been designed and synthesized on a 1,8-naphthalimide scaffold. The probe exhibited a high selectivity for HOCl over various reactive oxygen species (ROS) with a fast response and a large fluorescence enhancement in aqueous media. Confocal microscopy imaging of living cells indicated that the probe was able to accumulate in lysosomes and was successfully applied to imaging exogenous HOCl in living cells. Attempts of using Lyso-NI-Se to image HOCl in stimulated RAW264.7 cells failed, probably due to the absence of endogenous HOCl in lysosomes or the undesirable detection limit.
Selective Difunctionalization of Unactivated Aliphatic Alkenes Enabled by a Metal-Metallaaromatic Catalytic System
Cui, Fei-Hu,Hua, Yuhui,Lin, Yu-Mei,Fei, Jiawei,Gao, Le-Han,Zhao, Xiaodan,Xia, Haiping
supporting information, p. 2301 - 2310 (2022/02/10)
The design of organometallic catalysts is crucial in the development of catalytic reactions. Herein, we describe a heterometallic [Os-Cu] complex with the characteristics of bimetallics, metallaaromatics, and pincer complexes. This complex serves as a highly effective catalyst for selective amino- and oxyselenation of unactivated alkenes. More than 80 examples including challenging substrates of unsymmetric aliphatic alkenes and amine-based nucleophiles in such reactions are provided. These reactions produce 1,2-difunctionalized products with good yields and high levels of chemo-, regio-, and stereoselectivity. Our studies revealed the following: (i) The usually inert osmium center activates the N- or O-centered nucleophiles. (ii) The copper-osmium bonding and its cooperative effects play essential roles in control the selectivity by bringing the reaction components into close proximity. (iii) The metallaaromatic moiety helps to stabilize the intermediate. These findings provide a versatile platform for catalyst design based on metal-metallaaromatic cooperative effects that have not been attained previously with bimetallic complexes.
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
Palladium Nanoparticles Supported on Nitrogen-rich Containing Melamine-based Microporous Covalent Triazine Polymers as Efficient Heterogeneous Catalyst for C?Se Coupling Reactions
Sadhasivam, Velu,Balasaravanan, Rajendiran,Chithiraikumar, Chinnadurai,Siva, Ayyanar
, p. 3833 - 3844 (2018/07/30)
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.
DMSO/iodine-catalyzed oxidative C-Se/C-S bond formation: A regioselective synthesis of unsymmetrical chalcogenides with nitrogen- or oxygen-containing arenes
Saba, Sumbal,Rafique, Jamal,Braga, Antonio L.
, p. 3087 - 3098 (2016/05/24)
A convenient metal-free and solvent-free iodine-catalyzed regioselective greener protocol to access different types of unsymmetrical chalcogenides with nitrogen- or oxygen-containing arenes through oxidative C-Se/C-S formation via direct C(sp2)-H bond activation was developed. The products were obtained in good to excellent yields using [O or N]-containing arenes, half equiv. of various odorless diorganyl dichalcogenides (S/Se), iodine (20 mol%) as the catalyst and 3 equiv. of DMSO as the oxidant, applying MW irradiation for 10 min.
Copper-catalyzed direct arylselenation of anilines by C-H bond cleavage
Ricordi, Vanessa G.,Thurow, Samuel,Penteado, Filipe,Schumacher, Ricardo F.,Perin, Gelson,Lenard?o, Eder J.,Alves, Diego
supporting information, p. 933 - 939 (2015/03/30)
We describe here an efficient and regioselective synthesis of arylselanyl anilines by copper-catalyzed direct arylselenation of arylamines. Using a catalytic amount of copper iodide in dimethyl sulfoxide at 110 °C under an air atmosphere, a range of aryls
Visible light photocatalyzed direct conversion of aryl-/heteroarylamines to selenides at room temperature
Kundu, Debasish,Ahammed, Sabir,Ranu, Brindaban C.
, p. 1814 - 1817 (2014/04/17)
A novel strategy for the direct conversion of aryl- and heteroarylamines to selenides has been developed via diazotization of amines with tert-butyl nitrite in neutral medium followed by reaction with diaryl/diheteroaryl/dialkyl diselenides in one pot under photocatalysis at room temperature in the absence of any metal. This reaction is also applied for the synthesis of tellurides. The selenylation of heteroarylamine by this protocol is of much significance because of the difficulty in diazotization of these molecules by a standard diazotization method in acid medium.
Solvent-controlled halo-selective selenylation of aryl halides catalyzed by Cu(II) supported on Al2O3. A general protocol for the synthesis of unsymmetrical organo mono- and bis-selenides
Chatterjee, Tanmay,Ranu, Brindaban C.
, p. 7145 - 7153 (2013/08/23)
Alumina-supported Cu(II) efficiently catalyzes selenylation of aryl iodides and aryl bromides by diaryl, dialkyl, and diheteroaryl diselenides in water and PEG-600, respectively, leading to a general route toward synthesis of unsymmetrical diaryl, aryl-alkyl, aryl-heteroaryl, and diheteroaryl selenides. A sequential reaction of bromoiodobenzene with one diaryl/diheteroaryl/dialkyl diselenide in water and another diaryl/diheteroaryl/dialkyl diselenide in PEG-600 in the second step produces unsymmetrical diaryl, diheteroaryl, or aryl-alkyl bis-selanyl benzene. A library of functionalized organo mono- and bis-selenides, including a potent biologically active molecule and a couple of analogues of bioactive selenides, were obtained in high yields by this protocol. The reactions are chemoselective and high yielding. The Cu-Al2O 3 catalyst is recycled for seven runs without any appreciable loss of activity.
Palladium-catalyzed cross-coupling of PhSeSnBu3 with aryl and alkyl halides in ionic liquids: A practical synthetic method of diorganyl selenides
Zhao, Hong,Hao, Wenyan,Xi, Zhiwen,Cai, Mingzhong
experimental part, p. 2661 - 2665 (2012/01/04)
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.
A near-IR reversible fluorescent probe modulated by selenium for monitoring peroxynitrite and imaging in living cells
Yu, Fabiao,Li, Peng,Li, Guangyue,Zhao, Guangjiu,Chu, Tianshu,Han, Keli
, p. 11030 - 11033 (2011/09/14)
We have developed a near-IR reversible fluorescent probe containing an organoselenium functional group that can be used for the highly sensitive and selective monitoring of peroxynitrite oxidation and reduction events under physiological conditions. The probe effectively avoids the influence of autofluorescence in biological systems and gave positive results when tested in both aqueous solution and living cells. Real-time images of cellular peroxynitrite were successfully acquired.
