4237-00-7Relevant academic research and scientific papers
A green and efficient route for P ? S ? C bond construction using copper ferrite nanoparticles as catalyst: a TD-DFT study
Moghaddam, Firouz Matloubi,Daneshfar, Maryam,Azaryan, Reza
, p. 311 - 315 (2020/11/02)
Magnetic nanoparticles of CuFe2O4 were applied as catalyst system for one-pot thiophosphate synthesis via the reaction of aryl sulfonyl chlorides with H-phosphonates under conventional heating conditions. This is an extremely efficient and green method for thiophosphate synthesis under base- and solvent-free conditions. Various thiophosphates were obtained in good to excellent yields under the optimized reaction conditions in a short time. The catalyst can be easily recycled from the reaction by an external magnetic field and reused for the next run. In this study, TD-DFT B3LYP/6-31 + G(d) calculations are in good accord with the experimental results. A comparison between experimental and theoretical UV-vis absorption spectra of the thiophosphate 3k has been carried out; and a small hypsochromic shift (only ~ 2 nm) was displayed at maximum absorption. The aim of this work is to investigate the best method and basis set for thiophosphate compounds; therefore, predictions for these compounds can be performed in theoretical studies.
Base-controlled Fe(Pc)-catalyzed aerobic oxidation of thiols for the synthesis of S-S and S-P(O) bonds
Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
, p. 4236 - 4242 (2018/06/21)
Fe(Pc)-Catalyzed aerobic oxidation of thiols for the synthesis of disulfides has been developed under mild reaction conditions. In addition, an aerobic oxidative cross-dehydrogenative coupling (CDC) reaction of thiols with P(O)-H compounds (H-phosphonates and H-phosphine oxide) for the formation of S-P(O) bonds has been demonstrated under the Fe(Pc) catalysis system with a base additive. Control experiments revealed that the use of a base (DIPA) in this system controls the synthetic pathways in which thiophosphates are formed.
Magnetically recyclable Cu-BTC@Fe3O4 composite-catalyzed C(aryl)-S-P bond formation using aniline, P(O)H compounds and sulfur powder
Wang, Liang,Yang, Sen,Chen, Le,Yuan, Sheng,Chen, Qun,He, Ming-Yang,Zhang, Zhi-Hui
, p. 2356 - 2361 (2017/07/22)
A Cu-BTC@Fe3O4 composite was prepared and exhibited good catalytic activity toward the synthesis of S-aryl phosphorothioates. The three-component reaction involved the coupling of in situ generated aryl diazonium salts from aniline, R2P(O)H, and sulfur powder, allowing the facile and direct formation of C(aryl)-S-P bonds. A broad scope of substrates survived the reaction conditions to afford the corresponding products in good to excellent yields. Moreover, this heterogeneous catalyst could be magnetically recovered and reused without significant loss of its activity after six cycles.
Iodine-catalyzed sulfenylation of H-phosphonates with diaryl disulfides under metal, base and solvent-free conditions
Wu, Xiang-Mei,Hong, Yu-Xiang
, p. 49 - 55 (2017/03/08)
Background: Although the exploitation of facile and efficient preparation for S-aryl phosphorothioates has gained considerable interest, there is still great demand for the development of a direct, convenient and especially environmentally benign protocol
A S-aryl thiophosphate preparation method
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Paragraph 0095-0099, (2017/01/12)
The invention discloses a preparation method of S-aryl phosphorothioate. The preparation method comprises the following steps of (1) adding a copper catalyst, an aryl sulfonyl chloride and phosphite in an organic solvent, reacting for 12-24 h at a temperature of 60-150 DEG C and cooling to a room temperature to obtain a reaction liquid; and (2) concentrating the reaction liquid, separating and purifying to obtain S-aryl phosphorothioate. According to the preparation method of S-aryl phosphorothioate, a one-pot method is adopted; copper is used as the catalyst; economical and easily available aryl sulfonyl chloride and phosphite are used as the raw materials; and a coupling reaction is carried out directly to generate corresponding S-aryl phosphorothioate, without adding alkali in air. A synthetic system has a relatively wide application scope, is compatible with a plurality of groups such as alkoxy, aryl, halogen and acyloxy. The preparation method provided by the invention is simple in process, convenient for operations and mild in reaction conditions, has a wide substrate range and relatively high yield, and is suitable for popularization and application.
Synthesis of S-Aryl Phosphorothioates by Copper-Catalyzed Phosphorothiolation of Diaryliodonium and Arenediazonium Salts
Zhang, Liangliang,Zhang, Pengbo,Li, Xueqin,Xu, Jian,Tang, Guo,Zhao, Yufen
, p. 5588 - 5594 (2016/07/13)
Green methods for the synthesis of S-aryl phosphorothioates have been developed based on copper-catalyzed multicomponent reactions involving diaryliodonium/arenediazonium salts, elemental sulfur, and R2P(O)H compounds. Most target products are obtained with these two methods in good to high yields at room temperature. These transformations allow the direct formation P-S and C-S bonds in one reaction.
Peroxide promoted metal-free thiolation of phosphites by thiophenols/disulfides
Wang, Jichao,Huang, Xin,Ni, Zhangqin,Wang, Sichang,Pan, Yuanjiang,Wu, Jun
, p. 7853 - 7859 (2015/09/15)
A metal-free oxidative P-S bonds coupling method for the synthesis of thiophosphates with DTBP as the oxidant is established. A wide range of functionalities are tolerated in the method. This method provides a facile way to synthesize thiophophates from readily available thiophenols/disulfides and phosphites.
Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates
Bai, Jie,Cui, Xiuling,Wang, Hui,Wu, Yangjie
supporting information, p. 8860 - 8863 (2014/08/05)
An efficient protocol for copper-catalyzed reductive cross-coupling of aryl sulfonyl chlorides with H-phosphonates has been developed. The various S-aryl phosphorothioates were afforded in up to 86% yield for 20 examples. This protocol features high effic
N-Chlorosuccinimide-promoted synthesis of thiophosphates from thiols and phosphonates under mild conditions
Liu, Yi-Chen,Lee, Chin-Fa
, p. 357 - 364 (2014/01/06)
A very simple N-chlorosuccinimide-promoted synthesis of thiophosphates through the coupling of thiols and phosphonates is reported. Notably, the reactions were carried out in the absence of a base. Functional groups including fluoro, bromo and trifluoromethyl are all tolerated by the reaction conditions employed. Both aryl and alkyl thiols are coupled smoothly with a broad spectrum of phosphonates to afford the corresponding thiophosphates in good to excellent yields.
A simple and convenient method for the synthesis of S-aryl phosphorothioates catalyzed by cesium hydroxide
Ouyang, Yue-Jun,Li, Yuan-Yuan,Li, Ning-Bo,Xu, Xin-Hua
, p. 1103 - 1105 (2014/01/06)
In the presence of a catalytic amount of cesium hydroxide, the corresponding S-aryl phosphorothioates can be obtained by the reactions of dialkyl phosphites with diaryldisulfides in excellent yields at room temperature, using DMSO as a solvent. The reaction mechanism was discussed. The method provides a new and expedient path for the preparation of S-aryl phosphorothioates.
