4537-05-7Relevant 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.]
Heterogeneously Ni-Pd nanoparticle-catalyzed base-free formal C-S bond metathesis of thiols
Mitamura, Kanju,Yatabe, Takafumi,Yamamoto, Kidai,Yabe, Tomohiro,Suzuki, Kosuke,Yamaguchi, Kazuya
supporting information, p. 3749 - 3752 (2021/04/21)
This study rationally designed a heterogeneously catalyzed system (i.e., using Ni-Pd alloy nanoparticles supported on hydroxyapatite (Ni-Pd/HAP) under an H2atmosphere) achieving an efficient base-free formal C-S bond metathesis of various thiolsviasuppression of the Ni catalysis deactivation.
Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings
Martín, M. Trinidad,Marín, Mario,Maya, Celia,Prieto, Auxiliadora,Nicasio, M. Carmen
supporting information, p. 12320 - 12326 (2021/08/09)
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.
Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
, p. 2707 - 2712 (2020/03/11)
An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
NiFe2O4 as a magnetically recoverable nanocatalyst for odourless C–S bond formation via the cleavage of C–O bond in the presence of S8 under mild and green conditions
Atashkar, Bahareh,Rostami, Amin,Rostami, Abed,Zolfigol, Mohammad Ali
, (2019/01/24)
We present green methodologies for one-pot and odourless syntheses of unsymmetric and symmetric diaryl sulfides via C─O bond activation using NiFe2O4 magnetic nanoparticles as a reusable heterogeneous nanocatalyst. The synthesis of unsymmetric sulfides is performed using the cross-coupling reaction of phenolic esters such as acetates, triflates and tosylates with arylboronic acid/S8 or triphenyltin chloride/S8 as thiolating agents in the presence of base and NiFe2O4 magnetic nanoparticles as a catalyst in poly(ethylene glycol) as solvent at 60–85°C. Also, the synthesis of symmetric diaryl sulfides from phenolic compounds using S8 as the sulfur source and NiFe2O4 as catalyst in dimethylformamide at 120°C is described. Using these protocols, the syntheses of various unsymmetric and symmetric sulfides become easier than using the available protocols due to the use of a magnetically reusable bimetallic nanocatalyst and avoiding the use of thiols and aryl halides.
Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
, p. 3048 - 3055 (2019/03/21)
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.
Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
Rostami, Abed,Rostami, Amin,Ghaderi, Arash,Gholinejad, Mohammad,Gheisarzadeh, Sajedeh
, p. 5025 - 5038 (2017/10/06)
Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.
Cu(ii)-catalyzed sulfide construction: both aryl groups utilization of intermolecular and intramolecular diaryliodonium salt
Wang, Ming,Wei, Jianpeng,Fan, Qiaoling,Jiang, Xuefeng
supporting information, p. 2918 - 2921 (2017/03/15)
A sulfur-iodine exchange protocol of diaryliodonium salts with inorganic sulfur salt was developed. Both aryl groups in the diaryliodonium salt were fully exerted in this transformation. Five- to eight-membered sulfur-containing heterocycles were achieved. Note that [1]benzothieno-[3,2-b][1]benzothiophene (BTBT) (an organic field-effect transistor (OFET) material) and Zaltoprofen were efficiently established through this method.
Diaryl thioether compound, and synthetic method and application thereof
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Paragraph 0110-0114, (2018/02/04)
The invention discloses a diaryl thioether compound, and a synthetic method and an application thereof. Various diaryl thioether compounds can be obtained through a reaction of a reaction raw material high iodine salt in dimethyl sulfoxide at 60-100DEG C under the action of an odorless sulfuration reagent, an alkali, a metal catalyst and a ligand for 3-12h. Sulfur is introduced in the later stage, so poisoning of sulfur to the metal catalyst and incompatibility of an oxidant in the early stage reaction are avoided; the above inorganic sulfur source is nontoxic and odorless; and two aryl groups in the high iodine salt are fully used, so the atom economy of the method is fully shown. The diaryl thioether compound prepared through the method can be further used to synthesize a photoelectric material BTBT and an anti-inflammatory drug zaltoprofen.
Aryl diazonium salt and thioacetamide: A catalyst free, efficient blend of an inexpensive arylating agent with "s" surrogate for sulphide synthesis
Bhojane, Jeevan Manohar,Sarode, Sachin Ashok,Nagarkar, Jayashreemilind
, p. 90046 - 90050 (2016/10/07)
Novel, facile C-S and S-S bond coupling reactions were achieved by using an aryl diazonium salt as an arylating agent and thioacetamide as a sulphur surrogate. The reaction proceeds smoothly at room temperature without using any transition metal catalyst, ligand or base. Aryl diazonium salts undergo rapid reactions with thioacetamide at room temperature to give the desired products in a much shorter period than the previously reported metal catalysed protocols.
