52258-16-9Relevant academic research and scientific papers
Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates
Kang, Jun-Chen,Li, Zi-Hao,Chen, Chao,Dong, Li-Kun,Zhang, Shu-Yu
supporting information, p. 15326 - 15334 (2021/10/25)
Herein, we have reported a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis. This protocol uses sulfinates as the sulfur source, and various thioethers could be synthesized under mild conditions. By mechanism exploration, we find that a cascade chemical step is allowed on the electrode interface and could alter the reaction pathway in paired electrolysis, whose findings could help the discovery of novel cascade reactions with unique reactivity.
Nickel-Catalyzed Decarbonylative Thioetherification of Acyl Fluorides via C-F Bond Activation
You, Jingwen,Chen, Qiang,Nishihara, Yasushi
supporting information, p. 3045 - 3050 (2021/05/31)
Nickel-catalyzed decarbonylative thioetherification of acyl fluorides has been developed. This transformation allows an array of acyl fluorides to react with thiophenols. A wide range of functional groups are well tolerated and the corresponding sulfides can be obtained in good to excellent yields. This protocol provides the formation of diverse carbon-sulfur bonds via a highly efficient decarbonylative process.
Ni-catalyzed C–S bond cleavage of aryl 2-pyridyl thioethers coupling with alkyl and aryl thiols
Wang, Cheng-Yi,Tian, Rui,Zhu, Yong-Ming
, (2021/09/29)
A nickel-catalyzed C–SPy bond activation reactions to produce a variety of thioethers has been developed. The reaction is promoted by a user-friendly, inexpensive, air and moisture-stable Ni precatalyst. Various aryl 2-pyridyl thioethers and a wide range of alkyl and aryl thiols substrates were tolerated in this process which afforded products in moderate to excellent yields.
Forging C?S(Se) Bonds by Nickel-catalyzed Decarbonylation of Carboxylic Acid and Cleavage of Aryl Dichalcogenides
Zhou, Jing-Ya,Zhu, Yong-Ming
, p. 2452 - 2461 (2021/06/28)
A nickel-catalyzed decarbonylation of carboxylic acids cross-coupling protocol has been developed for the straightforward C?S(Se) bond formation. This reaction is promoted by a commercially-available, user-friendly, inexpensive, air and moisture-stable nickel precatalyst. Various carboxylic acids and a wide range of aryl dichalcogenide substrates were tolerated in this process which afforded products in good to excellent yields. In addition, the present reaction can be conducted on gram scale in good yield.
Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2
Wang, Rongkang,Chen, Fangming,Jiang, Lvqi,Yi, Wenbin
supporting information, p. 1904 - 1911 (2021/02/12)
An efficient electrochemical synthesis approach of various unsymmetrical thioethers and arylboronates has been developed. Bench stable arylazo sulfones were used as radical precursors for carbon-heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and even added bases, but also exhibited favorable functional group tolerance. (Figure presented.).
An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols
Asadpour, Mohammad,Azizzade, Meysam,Ghasemi, Mehran,Jafarpour, Farnaz,Rajai-Daryasarei, Saideh
supporting information, p. 727 - 734 (2020/02/25)
A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C-S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.
Direct C-S bond formation: Via C-O bond activation of phenols in a crossover Pd/Cu dual-metal catalysis system
Khakyzadeh, Vahid,Rostami, Abed,Veisi, Hojat,Shirmardi Shaghasemi, Behzad,Reimhult, Erik,Luque, Rafael,Xia, Yuanzhi,Darvishi, Sima
, p. 4491 - 4497 (2019/05/17)
A dual-metal catalysis system including a newly prepared nanoparticle [SiO2@organic-linker(OL)@Pd(II)] and CuI was introduced with ultra-high catalytic activity (high turnover number (TON), up to 19000) to a one-pot and odorless synthesis of unsymmetrical aryl sulfides by crossover C-S bond formation. The reaction proceeds via C-O bond activation of phenols and direct C-S bond formation in the presence of S8 as an oddorless sulfur source and aryl boronic acids under mild conditions (room temperature). The catalyst could be recycled up to five times without an obvious change in its activity.
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.
Iodine-Promoted Tunable Synthesis of 2-Naphthyl Thioethers and 1-Naphthyl Thioethers
Bao, Yishu,Yang, Xiuqin,Dai, Zonghao,Ji, Suyu,Zhou, Qingfa,Yang, Fulai
supporting information, p. 2154 - 2158 (2019/04/13)
An iodine-promoted regioselective sulfenylation/deoxygenation/aromatization reaction of 1-tetralones with disulfides has been developed. This process could be modified to synthesize 2-naphthyl thioethers and 1-naphthyl thioethers in moderate to excellent
Forging C-S Bonds through Nickel-Catalyzed Aryl Anhydrides with Thiophenols: Decarbonylation or Decarbonylation Accompanied by Decarboxylation
Zhou, Jing-Ya,Tao, Shou-Wei,Liu, Rui-Qing,Zhu, Yong-Ming
, p. 11891 - 11901 (2019/10/11)
A nickel-catalyzed decarbonylation or decarbonylation accompanied by decarboxylation cross-coupling reaction of aryl anhydrides with thiophenols as coupling partners was disclosed. This method is promoted by a commercially available, moisture-stable, and inexpensive nickel(II) precatalyst. The process can tolerate a variety of functional groups using ubiquitous aryl anhydrides as cross-coupling precursors to produce thioethers in moderate to excellent yields.
