- Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
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A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
- Lam, Long Yin,Ma, Cong
-
supporting information
p. 6164 - 6168
(2021/08/16)
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- Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
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Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
- Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
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p. 10829 - 10837
(2021/07/28)
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- N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides
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An efficient reduction of sulfoxides to sulfides mediated by N-bromosuccinimide (NBS)/HCl system has been developed. This protocol shows good functional group compatibility as well as broad substrates scope with operational simplicity.
- Wang, Jianqiang,Shi, Fangmin,Dai, Dongyan,Xiong, Liping,Yang, Yongpo
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supporting information
p. 439 - 443
(2021/02/03)
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- Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings
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Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.
- Martín, M. Trinidad,Marín, Mario,Maya, Celia,Prieto, Auxiliadora,Nicasio, M. Carmen
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supporting information
p. 12320 - 12326
(2021/08/09)
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- Spiroconjugated Tetraaminospirenes as Donors in Color-Tunable Charge-Transfer Emitters with Donor-Acceptor Structure
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Charge-transfer emitters are attractive due to their color tunability and potentially high photoluminescence quantum yields (PLQYs). We herein present tetraaminospirenes as donor moieties, which, in combination with a variety of acceptors, furnished 12 charge-transfer emitters with a range of emission colors and PLQYs of up to 99 %. The spatial separation of their frontier molecular orbitals was obtained through careful structural design, and two DA structures were confirmed by X-ray crystallography. A range of photophysical measurements supported by DFT calculations shed light on the optoelectronic properties of this new family of spiro-NN-donor-acceptor dyes.
- Adachi, Chihaya,Adler, Florin,Chan, Chin-Yiu,Esser, Birgit,Grenz, David C.,Hermann, Mathias,Rose, Daniel,W?ssner, Jan S.,Wilbuer, Jennifer
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supporting information
(2021/12/22)
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- An effective thermally activated delayed fluorescence host material for highly efficient blue phosphorescent organic light-emitting diodes with low doping concentration
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A thermally activated delayed fluorescence (TADF) material BCz-2SO has been designed and synthesized as host for blue phosphorescent organic light-emitting diodes (OLEDs). Photophysical studies and theoretical calculations show that the molecule has a small singlet-triplet energy gap (ΔEST) of 0.345 eV, which is beneficial to the reverse energy transferring between the singlet and triplet state. Thanks to the TADF property, the triplet energy can be transmitted to the singlet state through reverse intersystem crossing (RISC), and then transmitted to the guest through the Fo?rster energy transfer (FET) to achieve 100% utilization of energy. Thus, the triplet–triplet annihilation (TTA) of the blue phosphor can be avoided by the extremely low doping concentration of 1%. By using BCz-2SO as the host of FIrpic, the solution-processed blue phosphorescent device achieves the maximum current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE) and highest brightness of 16.38 cd A?1, 9.04 lm W?1, 7.8% and 16,537 cd m-2, respectively. It demonstrates that one can employ the solution-processed method to prepare the high performance phosphorescent OLEDs using the TADF host material we have developed.
- Liu, Yan,Pan, Jie,Chen, Feng,Gao, Kun,Zhu, Aiyun,Wang, Ruoxian,Yue, Xuan,Ban, Xinxin
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- CuMoO4 Bimetallic Nanoparticles, An Efficient Catalyst for Room Temperature C?S Cross-Coupling of Thiols and Haloarenes
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CuII catalyst is less efficient at room temperature for C?S cross-coupling. C?S cross-coupling by CuII catalyst at room temperature is not reported; however, doping of copper with molybdenum metal has been realized here to be more efficient for C?S cross-coupling in comparison to general CuII catalyst. The doped catalyst CuMoO4 nanoparticle is found to be more efficient than copper. The catalyst works under mild conditions without any ligand at room temperature and is recyclable and effective for a wide range of thiols and haloarenes (ArI, ArBr, ArF) from milligram to gram scale. The copper-based bimetallic catalyst is developed and recognized for C?S cross-coupling of haloarenes with alkyl and aryl thiols.
- Panigrahi, Reba,Sahu, Santosh Kumar,Behera, Pradyota Kumar,Panda, Subhalaxmi,Rout, Laxmidhar
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p. 620 - 624
(2019/12/27)
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- Bimetallic BaMoO4 nanoparticles for the C-S cross-coupling of thiols with haloarenes
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We disclosed new bimetallic BaMoO4 nanoparticles for the C-S cross-coupling reaction. The C-S cross-coupling reaction of alkyl/aryl thiols with haloarenes was accomplished with high yields. The reaction has good functional group tolerance and selectivity. This is an efficient protocol for synthesizing the building blocks of pharmaceuticals containing C-S bonds. The catalyst is recyclable. The unactivated bromo- and 4-acetyl fluoro-arenes can well couple to afford thioethers in high yields. The reaction is believed to proceed by oxidative addition and reductive elimination.
- Panda, Subhalaxmi,Sahu, Santosh Kumar,Behera, Pradyota Kumar,Panigrahi, Reba,Garnaik, Bamakanta,Rout, Laxmidhar
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supporting information
p. 2500 - 2504
(2020/02/20)
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- A template free protocol for fabrication of a Ni(ii)-loaded magnetically separable nanoreactor scaffold for confined synthesis of unsymmetrical diaryl sulfides in water
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In the present report, an environmentally benign magnetically recoverable nickel(ii)-based nanoreactor as a heterogeneous catalyst has been developedviaa template free approach. The catalytic performance of the synthesized catalyst is assessed in the confined oxidative coupling of arenethiols with arylhydrazines to form unsymmetrical diaryl sulfides under aerobic conditions. The salient features of our protocol include oxidant- and ligand-free conditions, use of water as a green solvent, room temperature and formation of nitrogen and water as the only by-products. Moreover, a broad range of functional groups are tolerated well and provide the corresponding diaryl sulfides in moderate to good yields. Moreover, the heterogeneous nature of the catalyst permits facile magnetic recovery and reusability for up to seven runs, making the present protocol highly desirable from industrial and environmental standpoints.
- Arora, Gunjan,Gaur, Rashmi,Gupta, Radhika,Rana, Pooja,Sharma, Rakesh Kumar,Yadav, Manavi,Yadav, Priya
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p. 19390 - 19396
(2020/06/04)
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- Microwave-Assisted Copper Slag-Catalyzed Green S-Arylation of Arenethiols with Arylboronic Acids
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Abstract: Diaryl sulfides have been synthesized in moderate to excellent yield by S-arylation of arenethiols with arylboronic acids using copper slag as a catalyst. Copper slag is a by-product obtained from smelting and refining of copper. Conventional heating method has been compared with the microwave-assisted technique. The proposed microwave-assisted synthesis provides excellent yields of diaryl sulfides in a short time (10 min) and is ligand-free, green, and cost-effective.
- Gavane, D. S.,Jambhorkar, V. S.,Kale, B. D.,Karnik, K. S.,Khandare, A. L.,Narula, I. S.,Rajhans, A. P.,Sarkate, A. P.
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p. 1300 - 1303
(2020/10/02)
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- Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
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A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
- Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
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p. 2447 - 2458
(2020/04/15)
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- X-ray structurally characterized Mo (VI), Fe (III) and Cu (II) complexes of amide-imine conjugate: (bio)catalytic and histidine recognition studies
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An amide-imine conjugate, (E)-N′-((2-hydroxybenzen-1-yl) methylene)-4-methylbenzohydrazide (H2LPTASAL), derived from 4-methyl-benzoic acid hydrazide (PTA) and 2-hydroxybenzaldehyde is used to prepare Mo (VI), Cu (II) and Fe (III) complexes. The X-ray structurally characterized complexes have been explored as catalyst for amine assisted asymmetric ring opening (ARO) of epoxide, carbon-heteroatom cross-coupling and ethyl benzene oxidation. In addition, their catecholase like activities have thoroughly been investigated. Moreover, the Cu (II) complex selectively recognizes histidine by fluorescence spectroscopy.
- Ta, Sabyasachi,Ghosh, Milan,Salam, Noor,Das, Jayanta,Islam, Manirul,Brand?o, Paula,Félix, Vítor,Sanmartin, Jesus,Das, Debasis
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- Preparation method of 4-phenylmercaptothiophenol
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The invention provides a preparation method of 4-phenylthiolthiophenol. The preparation method comprises the following steps: performing a bromination reaction on diphenyl sulfide and a bromination reagent to prepare 4-bromodiphenyl sulfide, performing a
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-
Paragraph 0056-0059; 0067; 0068
(2020/07/15)
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- Controlled Ni-catalyzed mono- and double-decarbonylations of α-ketothioesters
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A method for Ni-catalyzed controlled decarbonylation of α-ketothioesters is described. Mono- and double-decarbonylations, which gave thioesters and thioethers, respectively, were selectively achieved by changing the ligand. A fundamental study of Ni-catalyzed decarbonylation of α-ketothioesters is presented.
- Zheng, Zhao-Jing,Jiang, Cheng,Shao, Peng-Cheng,Liu, Wen-Fei,Zhao, Tian-Tian,Xu, Peng-Fei,Wei, Hao
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p. 1907 - 1910
(2019/05/02)
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- Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
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A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
- Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
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p. 3048 - 3055
(2019/03/21)
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- Aryldithiocarbamates as thiol alternatives in Cu-catalyzed C(aryl)-S coupling reactions using aryldiazonium tetrafluoroborate salts
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An efficient method for the synthesis of unsymmetrical diaryl sulfides has been developed by the C-S cross coupling of aryldithiocarbamates and aryldiazonium salts in the presence of CuI-2,2′-bipyridine and Zn. Aryldithiocarbamate compounds have been used here as thiol substitutes. The protocol shows wide substrate scope and good yields of the products.
- Dutta, Soumya,Saha, Amit
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p. 9360 - 9366
(2019/11/13)
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- Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity
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A simple and efficient approach of C-S cross-coupling of a wide variety of (hetero)aryl thiols and (hetero)aryl halides under mild conditions, mostly at room temperature, catalyzed by well-defined singlet diradical Ni(II) catalysts bearing redox noninnocent ligands is reported. Taking advantage of ligand centered redox events, the high-energetic Ni(0)/Ni(II) or Ni(I)/Ni(III) redox steps were avoided in the catalytic cycle. The cooperative participation of both nickel and the coordinated ligands during oxidative addition/reductive elimination steps allowed us to perform the catalytic reactions under mild conditions.
- Sikari, Rina,Sinha, Suman,Das, Siuli,Saha, Anannya,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
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p. 4072 - 4085
(2019/04/01)
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- Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O2/Air
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A practical and switchable method for the synthesis of aryl sulfones and sulfoxides via sulfide oxidation was developed. The chemoselectivities of products were simply controlled by reaction temperature using O2/air as the terminal oxidant and oxygen source. The broad substrate scope, easy realization of gram-scale production, and the simplification of a sulfide oxidation system render the strategy attractive and valuable.
- Cheng, Zhen,Sun, Pengchao,Tang, Ailing,Jin, Weiwei,Liu, Chenjiang
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supporting information
p. 8925 - 8929
(2019/11/14)
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- Syntheses of Thioethers and Selenide Ethers from Anilines
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In this study, a general procedure was proposed for synthesizing thioethers and selenide ethers from anilines under solvent-free and transition-metal-free conditions. Thioethers were formed when anilines reacted with thiols under blue light-emitting-diode (LED) irradiation at room temperature without a photocatalyst. When reactions were performed using anilines and diselenides, the corresponding selenide ethers were obtained with satisfactory to excellent yields. The reaction was performed under photocatalyst-free and solvent-free conditions without blue LEDs. The advantages of this system include convenient operations, mild reaction conditions, satisfactory functional group tolerance, and late-stage selenylation of drug molecules.
- Shieh, Yi-Chen,Du, Kai,Basha, R. Sidick,Xue, Yung-Jing,Shih, Bo-Hao,Li, Liang,Lee, Chin-Fa
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p. 6223 - 6231
(2019/05/24)
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- C-S cross-coupling reaction using novel and green synthesized CuO nanoparticles assisted by Euphorbia maculata extract
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In the present study, biosynthesis of CuO nanoparticles using a rapid, eco-friendly, cost-effective and efficient method has been reported employing aqueous Euphorbia maculata extract as mild, renewable and non-toxic reducing and capping agents without adding any surfactants. The biogenic and green method has some benefits compared to conventional physical and chemical methods. It is simple, cheap and environmentally friendly. The biosynthesized CuO NP displayed a color change pattern (from sky blue to black) on preparation and presented its respective broad peak at 365?nm, which was analyzed by UV–Vis spectroscopy. Using the FT-IR analysis, biomolecules in E. maculata extract which are responsible for bioreduction activity and synthesize of CuO NP, were identified. The XRD, EDX and FESEM results confirmed the successful synthesis of CuO nanoparticles of 18?nm sizes, with spherical and sponge crystal structure. The catalytic activity of biosynthesized CuO NPs was studied in C-S cross-coupling reaction. This method has the advantages of high yields, easy work-up, and simple reusability. The recovered CuO NP can be reused four times without any considerable loss of its catalytic activity.
- Alinezhad, Heshmatollah,Pakzad, Khatereh
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- One-pot synthesis method for substituted diphenyl sulfide
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The invention relates to a one-pot synthesis method for substituted diphenyl sulfide. The process comprises the following steps: adding thiophenol or diphenyl disulfide and derivatives thereof into asolvent, dropwise adding sulfonyl chloride for a reaction so as to obtain a substituted benzene sulfuryl chloride solution, removing a part of the solvent at a normal pressure, adding Lewis acid, thendropwise adding substituted benzene for a Friedel-Crafts reaction, and carrying out distillation or recrystallization so as to obtain the substituted diphenyl sulfide. The method provided by the invention has the advantages of high safety, simple and convenient raw material recovery, greatly-reducedpurifying difficulty, easily-available raw materials, simple unit operation, low requirements on reaction equipment, mild reaction conditions, high yield and content and applicability to industrial production; and the content of the finally obtained substituted diphenyl sulfide product generally reaches 98% or more.
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-
Paragraph 0055; 0056; 0057
(2019/01/08)
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- Phenyldithiocarbamates: Efficient Sulfuration Reagents in the Chan–Lam Coupling Reaction
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The Chan–Lam coupling reaction starting from phenyldithiocarbamates and phenylboronic acids is reported. To avoid using the volatile, hazardous, and foul-smelling thiols, which are sometimes expensive and not sufficiently available, phenyldithiocarbamates can be employed. They are demonstrated to be good sulfuration reagents in the Chan–Lam coupling to prepare biaryl sulfides. By using this protocol, dithiocarbamate substrates with a wide range of functional groups including electron-rich and electron-deficient ones are explored to obtain the desired substituted biaryl sulfides smoothly. This method is ligand-free, has a broad substrate scope, enables good yields, and is easy to perform. It provides a facile and convenient preparation of biaryl sulfides.
- Cheng, Yu,Liu, Xing,Dong, Zhi-Bing
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p. 815 - 820
(2018/02/21)
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- SPS–Ni(II) pincer compounds of the type [Ni(phPS2)(P(C6H4-4-R)3)] Synthesis, characterization and catalytic evaluation in C–S cross-coupling reactions
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The synthesis and characterization of a series of SPS–Ni(II) pincer complexes with different para-substituted triphenylphosphines has been performed. The molecular structure of [Ni(phPS2)(PPh3)] (1) (phPS2H2 = PhP(C6H4-2-SH)2, bis(phenyl-2-thiol)phenylphosphine) was unequivocally determined by single crystal X-ray diffraction analysis. The metal centre exhibited a slightly distorted square planar geometry. The complexes showed a high catalytic activity in the C–S cross-coupling reaction of both alkyl- and aryl-disulfides with iodobenzenes for the production of non-symmetric sulfides. In general, the different para-substituted triphenylphosphine ligands do not affect the catalytic performance of the SPS–Ni(II) complexes. However, activity of the catalyst decreases with the steric hindrance of the different alkyl groups in the disulphide substrates.
- Gómez-Benítez, Valente,Valdés, Hugo,Hernández-Ortega, Simón,Germán-Acacio, Juan Manuel,Morales-Morales, David
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p. 144 - 148
(2017/10/13)
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- Asymmetric tris-heteroleptic iridium(iii) complexes containing three different 2-phenylpyridine-type ligands: A new strategy for improving the electroluminescence ability of phosphorescent emitters
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A series of asymmetric tris-heteroleptic Ir(iii) phosphorescent complexes adopting both IrLL′L′′ (Ir3-1 and Ir3-2) and IrLL′(acac) (Ir2-1 and Ir2-2) chemical constitution have been successfully prepared, where L, L′ and L′′ represent different ppy-type (2-phenylpyridine) ligands. The IrLL′L′′ asymmetric tris-heteroleptic Ir(iii) phosphorescent complexes Ir3-1 and Ir3-2 bearing three different ppy-type ligands can show better thermal stability, higher ΦP and improved ability of trapping both holes and electrons than IrLL′(acac) asymmetric analogs Ir2-1 and Ir2-2. Thanks to these advantages, Ir3-1 and Ir3-2, especially Ir3-2, can show phenomenal EL performance with a maximum external quantum efficiency (ηext) of 26.2%, a maximum current efficiency (ηL) of 88.7 cd A-1 and a maximum power efficiency (ηP) of 75.3 lm W-1, much higher than the data achieved by not only IrLL′(acac) asymmetric analogs Ir2-1 and Ir2-2, but also the traditional Ir(L)3 symmetric counterparts. To the best of our knowledge, these data represent the highest EL efficiencies ever achieved by the asymmetric ppy-type Ir(iii) phosphorescent complexes reported in the literature. All these encouraging results not only indicate the great potential of the unique asymmetric IrLL′L′′ structures bearing three different ppy-type ligands in improving the EL ability of ppy-type Ir(iii) phosphorescent emitters, but also represent important progress in the design and synthesis of new asymmetric ppy-type Ir(iii) phosphorescent complexes with high EL ability.
- Dang, Wanping,Yang, Xiaolong,Feng, Zhao,Sun, Yuanhui,Zhong, Daokun,Zhou, Guijiang,Wu, Zhaoxin,Wong, Wai-Yeung
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supporting information
p. 9453 - 9464
(2018/09/25)
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- Preparation method for 4-thiophenyl-thiophenol
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The invention discloses a preparation method for 4-thiophenyl-thiophenol. The preparation method comprises the following steps: with diphenyl sulfide as a raw material, subjecting the diphenyl sulfideto a halogenation reaction so as to obtain 4-halogeno diphenyl sulfide; subjecting the 4-halogeno diphenyl sulfide to a mercapto substitution reaction so as to obtain 4-thiophenyl-thiophenol salt; and subjecting the 4-thiophenyl-thiophenol salt to acidification. The preparation method provided by the invention avoids the use of substances like benzenethiol with pollution to the environment, and realizes highly-efficient cyclic recovery and utilization of reaction materials, solvents, water, etc. The preparation method provided by the invention does not discharge organic wastes, waste acid andwaste alkaline water, and is a green process for synthesis of the 4-thiophenyl-thiophenol.
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-
Paragraph 0064; 0101; 0102; 0103
(2018/07/06)
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- Nickel-Catalyzed C–S Coupling: Synthesis of Diaryl Sulfides Starting from Phenyldithiocarbamates and Iodobenzenes
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A nickel-catalyzed C–S bond-formation protocol for the synthesis of diaryl sulfides is described. In a reaction catalyzed by NiCl2, phenyldithiocarbamates react with iodobenzenes to give diaryl sulfides smoothly in good to excellent yields (66–93 %). The catalyst is cheap, the reaction is easy to carry out, the substrate scope is broad, and the yields are good. Thus, this gives an alternative way to prepare diaryl sulfides.
- Liu, Xing,Cao, Qiang,Xu, Wan,Zeng, Meng-Tian,Dong, Zhi-Bing
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p. 5795 - 5799
(2017/10/23)
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- Organic electroluminescence compound
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The invention discloses an organic electroluminescence compound of which the structure formula is shown in formula (I) shown in the specification, in the formula, R1 and R2 are independently selected from hydrogen atoms, chain alkyl or halogenated chain alkyl of C1-C20, substituted or unsubstituted cyclic alkyl of C3-C20, substituted or unsubstituted aryl of C6-C30, and substituted or unsubstituted heterocyclic aryl; Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl of C6-C30, and substituted or unsubstituted heterocyclic aryl of C6-C30; L1, L2 and L3 are independently selected from substituted or unsubstituted arylidene of C6-C30. The compound can be used as an OLED doping material, and an OLED device made of the compound has good fluorescence quantum efficiency, carrier balance transmission properties and thermal stability, is long in service life and has good prospects of application in the AMOLED industry.
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Paragraph 0044; 0045; 0046
(2017/11/04)
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- Ferromagnetic nanoparticle-supported copper complex: A highly efficient and reusable catalyst for three-component syntheses of 1,4-disubstituted 1,2,3-triazoles and C–S coupling of aryl halides
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A new nanocatalyst was synthesized by immobilization of 4′-(4-hydroxyphenyl)-2,2′:6′,2″-terpyridine/CuI complex on ferromagnetic nanoparticles through a surface modification (FMNPs@SiO2-TPy-Cu). This heterogeneous catalyst was characterized using various techniques including Fourier transform infrared and energy-dispersive X-ray spectroscopies, transmission and scanning electron microscopies, X-ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The resulting nanocatalyst presented excellent catalytic activity for the regioselective syntheses of 1,4-disubstituted 1,2,3-triazoles and thioethers. The thermally and chemically stable, benign and economical catalyst was easily recovered using an external magnet and reused in at least five successive runs without an appreciable loss of activity.
- Khodaei, Mohammad Mehdi,Bahrami, Kiumars,Meibodi, Farhat Sadat
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-
- A Highly Efficient Copper-Catalyzed Synthesis of Unsymmetrical Diaryl- and Aryl Alkyl Chalcogenides from Aryl Iodides and Diorganyl Disulfides and Diselenides
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An efficient and convenient protocol has been developed for the copper-catalyzed reaction of aryl iodides and diorganyl disulfides and diselenides. A variety of symmetrical and unsymmetrical diaryl- and aryl alkyl chalcogenides were synthesized with good functional group tolerance and chemoselectivity by using copper(I) iodide as a catalyst, 4′-(4-methoxyphenyl)-2,2′:6′,2′′-terpyridine as ligand, and KOH as base under an inert atmosphere.
- Movassagh, Barahman,Hosseinzadeh, Zhila
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supporting information
p. 777 - 781
(2016/03/12)
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- Polystyrene resin-supported CuI-cryptand 22 complex: a highly efficient and reusable catalyst for the formation of aryl–sulfur bonds in aqueous media
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The air and moisture stable polystyrene resin-supported copper(I) iodide-cryptand-22 complex (PS-C22-CuI) behaves as an efficient and robust heterogeneous catalyst in the cross-coupling reaction of aryl halides and thiols in aqueous media. Moreover, the heterogeneous catalyst can be easily recovered by filtration and reused for five cycles without significant loss in activity.
- Rezaei, Nasrin,Movassagh, Barahman
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supporting information
p. 1625 - 1628
(2018/03/29)
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- Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) catalyzed S-arylation of thiols with aryl halides in aqueous media
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Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) nano catalyst catalyzes selective C–S cross-coupling (S-arylation) reactions of thiols with aryl halides and avoids the formation of S–S (disulfide) homocoupling byproducts. The reactions were carried out in aqueous media using only 0.23?mol% palladium with high selectivity and short reaction time. The effects of the Pd0and Fe0moieties on the C–S cross-coupling reaction mechanism, yield, and selectivity were investigated. The yield and selectivity can be controlled by adjusting the order of adding the reactants and catalyst into the reaction medium. The X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), electron backscatter diffraction (EBSD) microscopy, energy dispersive X-ray (EDX) spectroscopy, and thermal gravimetric analysis (TGA) tools were used to characterize the catalyst. The C–S cross-coupling reaction process could be repeated up to six times without losing effectiveness. The metals leaching of Pd-PVP-Fe nanocatalyst after reusing cycles were investigated by atomic absorption spectroscopic (AAS) and EDX spectroscopy. The nature of Pd metal after the first run of the C–S cross-coupling reaction was studied by UV–vis spectrophotometry. The morphology of bimetallic nanocatalyst after the first run of the C–S cross-coupling reaction was investigated by SEM, EBSD, and EDX microscopy.
- Ghaderi-Shekhi Abadi, Parvaneh,Rafiee, Ezzat,Joshaghani, Mohammad
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p. 162 - 170
(2016/07/25)
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- A quick Chan-Lam C-N and C-S cross coupling at room temperature in the presence of square pyramidal [Cu(DMAP)4I]I as a catalyst
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A rapid and efficient protocol for C-N and C-S cross coupling has been developed using a new square pyramidal copper complex, [Cu(DMAP)4I]I. The complex was successfully synthesized via a disproportionation reaction of CuI and DMAP in DMSO. The catalytic activity of the complex was found to be excellent for Chan-Lam coupling reaction between aryl boronic acid and amine, amide, azide or thiol. The reaction could be carried out in the presence of only 2 mol% of the copper catalyst in methanol at room temperature within a short time.
- Roy, Subhasish,Sarma, Manas Jyoti,Kashyap, Bishwapran,Phukan, Prodeep
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supporting information
p. 1170 - 1173
(2016/01/15)
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- A highly efficient heterogeneous copper-catalyzed Chan-Lam coupling between thiols and arylboronic acids leading to diaryl sulfides under mild conditions
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The heterogeneous Chan-Lam coupling reaction between thiols and arylboronic acids was achieved in EtOH at room temperature in the presence of 5 mol % of MCM-41-immobilized 1,10-phenanthroline-copper(II) complex [MCM-41-1,10-Phen-CuSO4] with n-Bu4NOH (40% aq) as base under O2 atmosphere, yielding a variety of unsymmetrical diaryl sulfides in good to excellent yields under mild and green conditions. The new heterogeneous copper complex can easily be prepared by a simple procedure from commercially readily available and inexpensive reagents, and recovered by a simple filtration of the reaction solution and recycled for at least eight times without significant loss of catalytic activity.
- Lin, Yang,Cai, Mingzhong,Fang, Zhiqiang,Zhao, Hong
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p. 3335 - 3343
(2016/05/19)
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- Pyrazolopyrimidine derivative, preparation method, pharmaceutical composition and application
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The invention discloses a pyrazolopyrimidine derivative, a preparation method, a pharmaceutical composition and application. The invention provides the pyrazolopyrimidine derivative as shown in a formula I and stereoisomer or solvate or pharmaceutically acceptable salts or active metabolite or prodrug thereof. The pyrazolopyrimidine derivative as shown in the formula I has good inhibitory activity on Bruton's tyrosine kinase (Btk) and particularly has good in vitro and in vivo inhibitory activity on growth of tumor cells, and a good marketization prospect is achieved. Please see the formula I in the description.
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Paragraph 0314; 0315; 0316
(2017/07/19)
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- Optimized trade-offs between triplet emission and transparency in Pt(II) acetylides through phenylsulfonyl units for achieving good optical power limiting performance
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Three Pt(ii) acetylides have been prepared by coupling trans-[PtCl2(PBu3)2] to ethynyl aromatic ligands with electron-withdrawing phenylsulfonyl units in high yields (>85%). The investigation of their photophysical behavior has shown that the unique conjugation-breaking configuration of the -SO2- linker in the phenylsulfonyl units can afford a very short cut-off wavelength (λcut-off) of P) of the prepared Pt(ii) acetylides can be effectively enhanced from 0.52% to 15.92% through increasing the number of fluorine substituents on the phenylsulfonyl units in the organic ligands. Benefiting from their enhanced ΦP, the phenylsulfonyl-based Pt(ii) acetylides can exhibit comparable or even better optical power limiting (OPL) performance against 532 nm lasers than the state-of-the-art OPL material C60, indicating their great potential in the field of laser protection. All of these results have provided a new strategy to achieve consistency between high OPL ability and good transparency for OPL materials, representing a valuable attempt for coping with key problems in the field of nonlinear optics.
- An, Miao,Yan, Xiaogang,Tian, Zhuanzhuan,Zhao, Jiang,Liu, Boao,Dang, Feifan,Yang, Xiaolong,Wu, Yong,Zhou, Guijiang,Ren, Yixia,Gao, Loujun
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supporting information
p. 5626 - 5633
(2016/07/06)
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- High activity and stability in the cross-coupling of aryl halides with disulfides over Cu-doped hierarchically porous zeolite ZSM-5
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A Cu-doped zeolite ZSM-5 (Cu-ZSM-5-M) with a micro-meso-macroporous structure was directly synthesized, and it exhibits excellent catalytic activity and good recyclability in the cross-coupling of aryl halides with diphenyl disulfides. This feature should be attributed to the structural characteristics of meso-macropores and homogeneous dispersion of active Cuδ+ (δ 2) species in Cu-ZSM-5-M.
- Fu, Wenqian,Liu, Taotao,Fang, Zhongxue,Ma, Yuli,Zheng, Xiang,Wang, Wenchang,Ni, Xiaojun,Hu, Maolin,Tang, Tiandi
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supporting information
p. 5890 - 5893
(2015/03/30)
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- Copper nanopowder catalyzed cross-coupling of diaryl disulfides with aryl iodides in PEG-400
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An eco-friendly thiolation via diaryl disulfides and aryl iodides under ligand-free conditions is reported. With copper nanopowder as catalyst and PEG-400 as solvent, a variety of unsymmetrical diaryl sulfides are synthesized in good to excellent yields. The process is free from foul-smelling and unstable thiols and the copper nanopowder-PEG-400 catalytic system can be directly reused for four repetitive cycles.
- Wu, Xiang-Mei,Yan, Guo-Bing
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supporting information
p. 537 - 542
(2015/04/27)
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- Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides in Water
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Microwave-promoted C-S bond formation from thiols and aryl iodides in the presence of a copper catalyst is reported. A combination of copper(II) oxide and 1,10-phenanthroline catalyzes this reaction. A variety of aryl iodides react smoothly with thiols to provide the corresponding aryl sulfides in good to excellent yields. Notably, the reactions proceed in water with a short reaction time (30 minutes). This system shows broad functional-group tolerance; amino, chloro, bromo, acetyl, and nitro groups are unaffected by the reaction conditions.
- Chen, Yi-An,Badsara, Satpal Singh,Tsai, Wan-Ting,Lee, Chin-Fa
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p. 181 - 186
(2015/05/04)
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- Condensed-cyclic compound and organic light emitting device comprising the same
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Disclosed are a condensed-ring compound and an organic light emitting device comprising the same. The condensed-ring compound is represented by the chemical formula 1-2 or 1-3. The organic light emitting device comprising the condensed-ring compound can have a low driving voltage, high efficiency, high brightness, and long lifespan.COPYRIGHT KIPO 2016
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Paragraph 0496; 0497; 0498; 0499; 0500
(2016/10/07)
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- A high-efficiency hybrid white organic light-emitting diode enabled by a new blue fluorophor
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A new efficient blue fluorophor 4-(4-diphenylaminophenyl)diphenylsulfone (SOTPA), with high triplet energy and balanced charge-transporting properties, has been designed and synthesized, and showed impressive performance both as blue emitter and as a host for phosphors. A green phosphorescent device containing SOTPA as host showed a maximum external quantum efficiency (EQE) as high as 19.2%, suggesting almost complete triplet harvesting from the blue fluorophor by the green phosphor. Single-emitting layer (EML) F-P hybrid white organic light-emitting devices (WOLEDs) based on SOTPA also gave outstanding electroluminescence performance, with a low turn-on voltage of 2.7 V and maximum EQE and power efficiency (PE) of 15.4% and 40.2 lm W-1, respectively. Even at a practical brightness of 1000 cd m-2 the PE still remained as high as 24.1 lm W-1. This excellent performance represents the highest efficiency yet reported among single-EML F-P hybrid WOLEDs.
- Chen, Zhan,Liu, Xiao-Ke,Zheng, Cai-Jun,Ye, Jun,Li, Xin-Yang,Li, Fan,Ou, Xue-Mei,Zhang, Xiao-Hong
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supporting information
p. 4283 - 4289
(2015/05/13)
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- Arylation of diorganochalcogen compounds with diaryliodonium triflates: Metal catalysts are unnecessary
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Diaryliodonium triflates transfer an aryl group to the chalcogen atom of organic sulfides, selenides, and tellurides (but not ethers), in the absence of transition-metal catalyst, simply upon heating in chloroform or dichloroethane solution.
- Racicot, Lanne,Kasahara, Takahito,Ciufolini, Marco A.
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p. 6382 - 6385
(2015/02/19)
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- Nickel-Schiff base complex catalyzed C-S cross-coupling of thiols with organic chlorides
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We report an efficient, mild and convenient synthetic protocol for the C-S cross-coupling reaction of various aryl, benzyl, allyl chlorides and thiols using 5 mol % Nickel-Schiff base catalyst with NaOH as the base, in DMF at 70 °C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available organic chlorides and thiols.
- Gogoi, Prasanta,Hazarika, Sukanya,Sarma, Manas J.,Sarma, Kuladip,Barman, Pranjit
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p. 7484 - 7489
(2014/12/10)
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- An efficient protocol for the carbon-sulfur cross-coupling of sulfenyl chlorides with arylboronic acids using a palladium catalyst
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An efficient protocol for carbon-sulfur bond formation is developed, which involves the cross-coupling of sulfenyl chlorides and arylboronic acids catalyzed by a novel palladium-Schiff base complex. Good to high product yields, short reaction times, and mild reaction conditions are important features of this new method. Georg Thieme Verlag Stuttgart · New York.
- Gogoi, Prasanta,Kalita, Mukul,Barman, Pranjit
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p. 866 - 870
(2014/04/03)
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- Transition-metal-free acid-mediated synthesis of aryl sulfides from thiols and thioethers
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The preparation of diaryl and alkyl aryl sulfides via acid-mediated coupling of thiols and thioethers with diaryliodonium salts is reported. The scope, limitations, and mechanism of the transformation are discussed.
- Wagner, Anna M.,Sanford, Melanie S.
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p. 2263 - 2267
(2014/04/03)
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- Fabrication of magnetic amino-functionalized nanoparticles for S-arylation of heterocyclic thiols
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A series of uniformed mono-disperse magnetic nanoligands (MNLs) (CoFe2O4-NH2 (MNL A), Fe3O4@Si(CH2)3NH2 (MNL B), Fe3O4@Si(CH2)3/
- Liu, Yanhong,Zhou, Lincheng,Hui, Xinping,Dong, Zhenwen,Zhu, Hao,Shao, Yanming,Li, Yanfeng
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p. 49980 - 49985
(2014/12/10)
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- A highly active reusable polymer anchored copper catalyst for C-O, C-N and C-S cross coupling reactions
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A new furfural functionalized polymer-amine grafted with copper catalyst has been designed and employed for the N-arylation, O-arylation and S-arylation reactions under an open air condition to afford the corresponding coupled products in good to excellent yields. This solid supported catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), UV-vis spectroscopy and scanning electron microscope (SEM). The developed catalyst can be facilely recovered and reused five times without significant decrease in activity and selectivity. This result confirms that the polymer anchored complex was not leached during the reaction, suggesting the true heterogeneous nature of the catalyst.
- Islam, Sk.Manirul,Salam, Noor,Mondal, Paramita,Roy, Anupam Singha,Ghosh, Kajari,Tuhina
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- Catalytic C - S cross-coupling reactions employing Ni complexes of pyrrole-based pincer ligands
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A series of catalytic C - S coupling reactions utilizing well-defined Ni(II) PNP pincer complexes as precatalysts are reported (PNP = anion of 2,5-bis[(dialkyl/aryl-phosphino)methyl]pyrrole, abbreviated as P2RPyr). Coupling reactions employing a variety of aryl iodides and thiols in the presence of base and DMF proceed in good to excellent yield at 80°C with low catalyst loadings. Aryl bromides were found to result in substantially lower yields, and aryl chlorides were found to be unreactive under the catalytic conditions. In an effort to further understand the reactivity of the nickel PNP precatalysts, complexes of Ni(II) containing amide, alkoxide, hydroxide, thiolate, and hydrosulfide ligands have been prepared and examined in stoichiometric reactions relevant to carbon-heteroatom coupling. Full characterization of each nickel complex is provided, including solid-state structures. The results of stoichiometric reactions implicate a reduced Ni(I) species as the active catalyst, which forms by reduction of the Ni(II) precatalyst in the presence of excess thiolate. The facility in forming Ni(I) species is invoked to rationalize the observed activity among different Ni PNP precatalysts. (Chemical Equation Presented).
- Venkanna, Gopaladasu T.,Arman, Hadi D.,Tonzetich, Zachary J.
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p. 2941 - 2950
(2015/02/19)
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- A cyano-bridged copper(II)-copper(I) mixed-valence coordination polymer as a source of copper oxide nanoparticles with catalytic activity in C-N, C-O and C-S cross-coupling reactions
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A cyano-bridged copper(ii)-copper(i) mixed valence polymer, namely {[Cu4(CN)5(C5H5N)4]} n (1), was synthesized and characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis, differential scanning calorimetric analysis, and single crystal X-ray crystallography. Single crystal X-ray studies show that the coordination polymer 1 is linked by the cyanide anions with μ-1κN:2κC bridging modes to the copper centers, generating a two-dimensional (2D) layered network. The coordination polymer 1, upon pyrolyzing, yielded copper oxide nanoparticles, which have been characterized by TEM and powder X-ray diffraction. The catalytic properties of the resulting copper oxide nanoparticles have also been studied in C-N, C-O, and C-S cross-coupling reactions with aryl halides. The C-N, C-O and C-S coupling products were obtained in moderate to good yields (66-90%, 72-98%, and 50-86%), respectively. the Partner Organisations 2014.
- Trivedi, Manoj,Ujjain, Sanjeev Kumar,Sharma, Raj Kishore,Singh, Gurmeet,Kumar, Abhinav,Rath, Nigam P.
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p. 4267 - 4274
(2014/11/08)
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- Alkoxylation reactions of aryl halides catalyzed by magnetic copper ferrite
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Copper ferrite (CuFe2O4), which is easy-made, air-stable, low cost, easy separable, and regenerable, was applied as catalyst in an efficient method for C-O coupling reactions between various kinds of unactivated alkyl alcohols and aryl halides. This method only adopts 2.5% mol CuFe2O4 catalyst and selectively proceeds to C-O bond formation even sensitive substituents exist in the system.
- Yang, Shuliang,Xie, Wenbing,Zhou, Hua,Wu, Cunqi,Yang, Yanqin,Niu, Jiajia,Yang, Wei,Xu, Jingwei
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supporting information
p. 3415 - 3418
(2013/04/23)
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- Cu-grafted mesoporous organic polymer: A new recyclable nanocatalyst for multi-component, N-arylation and S-arylation reactions
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A new mesoporous Cu-MPTA-1 nanocatalyst has been synthesized via a simple and facile in situ radical polymerization of triallylamine in the presence of an organic-organic self-assembly of anionic surfactant SDS, followed by grafting of Cu(ii) at room temperature under an inert atmosphere. This nanomaterial has been characterized by elemental analysis, powder X-ray diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), UV-vis diffuse reflectance spectroscopy (DRS), thermogravimetric analysis (TGA), N2 adsorption-desorption studies, X-ray photoelectron spectroscopy (XPS) and EPR spectroscopy. Cu-MPTA-1 acts as an efficient heterogeneous nanocatalyst exhibiting a high catalytic activity for N-arylation and S-arylation reactions using water as a green solvent and also exhibits an excellent catalytic activity for the one-pot synthesis of propargylamines via a three component coupling of an alkyne, an amine and an aldehyde at room temperature. Moreover, the catalyst is easily recoverable and can be reused six times without an appreciable loss of catalytic activity in the three component coupling reaction. The highly dispersed Cu(ii) sites in the Cu-grafted mesoporous polymer could be responsible for the observed high activities of the Cu-MPTA-1 catalyst in the coupling reactions. No evidence of leached Cu from the catalyst during the course of the reaction has been observed, suggesting true heterogeneity in the catalytic process. The Royal Society of Chemistry.
- Salam, Noor,Kundu, Sudipta K.,Roy, Anupam Singha,Mondal, Paramita,Roy, Susmita,Bhaumik, Asim,Islam, Sk. Manirul
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p. 3303 - 3316
(2013/12/04)
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