56806-76-9Relevant academic research and scientific papers
Electrochemically driven synthesis of phosphorothioates from trialkyl phosphites and aryl thiols
Guo, Xiaqun,Li, Meichao,Liu, Xin,Shen, Zhenlu,Shi, Shuxian,Wu, Zengzhi,Zhao, Lingmin
, (2021/06/25)
A facile and elegant protocol for synthesis of phosphorothioates from trialkyl phosphites and aryl thiols via indirect electrochemical oxidation mediated by KI has been successfully developed. KI as a redox mediator, enabled the reaction of trialkyl phosp
Trichloroisocyanuric acid-promoted thiolation of phosphites by thiols
Chen, Yingying,Li, Meichao,Gong, Zhangshui,Shen, Zhenlu
, p. 19 - 27 (2020/08/06)
A simple and convenient method for the synthesis of thiophosphates by coupling of phosphites with thiols under mild conditions has been developed. The reactions were promoted by trichloroisocyanuric acid (TCCA) and were carried out at room temperature in
Synthetic method of thiophosphate compound
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Paragraph 0041-0042, (2020/05/30)
The invention discloses a synthetic method of a phosphorothioate compound. The preparation method comprises the following steps: with thiol as a reaction substrate and trichloroisocyanuric acid (TCCA)as an accelerant, reacting the reaction substrate and the accelerant in an organic solvent at normal temperature and normal pressure for 10-20 minutes, then adding phosphite triester, continuing reacting for 10-20 minutes, and after the reaction is finished, carrying out separation treatment to obtain the phosphorothioate compound. According to the synthesis method disclosed by the invention, thereaction is carried out at normal temperature and normal pressure without special requirements; reaction time is short; and reaction substrate universality is good.
Benign synthesis of thiophosphates, thiophosphinates and selenophosphates in neat condition using N-chalcogenoimides as the source of electrophilic sulfur/selenium
Mondal,Saha, Amit
, (2019/08/08)
A neat reaction protocol has been developed for synthesis of thiophosphate, thiophosphinate and selenophosphate compounds. N-chalcogenoimides have been used for chalcogenylation of P(O)H moieties of various H-phosphonates under solvent, catalyst and base free condition at room temperature in aerial atmosphere. Both S-aryl and S-alkyl phosphorothioate compounds were prepared by this method in good yields. Selenophosphates were also synthesized using N-(phenylseleno)phthalimide under solvent free condition.
Lewis Acid Promoted Aerobic Oxidative Coupling of Thiols with Phosphonates by Simple Nickel(II) Catalyst: Substrate Scope and Mechanistic Studies
Xue, Jing-Wen,Zeng, Miao,Zhang, Sicheng,Chen, Zhuqi,Yin, Guochuan
, p. 4179 - 4190 (2019/04/30)
Exploring new catalysts for efficient organic synthesis is among the most attractive topics in chemistry. Here, using Ni(OAc)2/LA as catalyst (LA: Lewis acid), a novel catalyst strategy was developed for oxidative coupling of thiols and phosphonates to phosphorothioates with oxygen oxidant. The present study discloses that when Ni(OAc)2 alone was employed as the catalyst, the reaction proceeded very sluggishly with low yield, whereas adding non-redox-active metal ions such as Y3+ to Ni(OAc)2 dramatically promoted its catalytic efficiency. The promotional effect is highly Lewis acidity dependent on the added Lewis acid, and generally, a stronger Lewis acid provided a better promotional effect. The stopped-flow kinetics confirmed that adding Y(OTf)3 can obviously accelerate the activation of thiols by Ni(II) and next accelerate its reaction with phosphonate to generate the phosphorothioate product. ESI-MS characterizations of the catalyst disclosed the formation of the heterobimetallic Ni(II)/Y(III) species in the catalyst solution. Additionally, this Ni(II)/LA catalyst can be applied in the synthesis of a series of phosphorothioate compounds including several commercial bioactive compounds. This catalyst strategy has clearly supported that Lewis acid can significantly improve the catalytic efficiency of these traditional metal ions in organic synthesis, thus opening up new opportunities in their catalyst design.
Electrochemical Dehydrogenative Phosphorylation of Thiols
Li, Chung-Yen,Liu, You-Chen,Li, Yi-Xuan,Reddy, Daggula Mallikarjuna,Lee, Chin-Fa
supporting information, p. 7833 - 7836 (2019/10/11)
We report herein a new approach for the synthesis of organothiophosphates from phosphonates and thiols through electrochemical reaction. The reactions were conducted without the addition of oxidant, transition-metal base, or base at room temperature. This
Cu(II)/Proline-Catalyzed Reductive Coupling of Sulfuryl Chloride and P(O)-H for P-S-C Bond Formation
Zhang, Xinghua,Wang, Dungai,An, Duo,Han, Boshi,Song, Xiang,Li, Liang,Zhang, Gaoqi,Wang, Lixian
, p. 1532 - 1537 (2018/02/10)
A considerably improved method for the Cu-catalyzed coupling of sulfuryl chloride with P(O)-H was described. Using commercially available l-proline as the ligand decreased the precatalyst loading, broadened the substrate scope and greatly promoted the efficiency of the coupling reaction. Moreover, gram-scale preparation, easy-to handle and recyclable catalyst featured this transformation.
Synthetic method for phosphorothiolate compounds
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Paragraph 0007; 0032-0034, (2018/12/01)
The invention discloses a synthetic method for phosphorothiolate compounds, and the reaction steps of the synthetic method are as follows: dissolving diaryl disulfide in the solution, taking oxygen inthe air as an oxidizing agent, stirring at room tempera
Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations
Kovács, Szabolcs,Bayarmagnai, Bilguun,Aillerie, Alexandre,Goo?en, Lukas J.
, p. 1913 - 1918 (2018/03/30)
New late-stage phosphorothiolation methods are disclosed that allow the efficient transfer of SP(O)(OR)2 groups to diversely functionalized substrates using nucleophilic and electrophilic reagents. The nucleophilic reagent, tetramethylammonium O,O-dimethyl phosphorothioate, was synthesized in near-quantitative yield from Me3SiP(O)(OMe)2, elemental sulfur and Me4NF. Its umpolung with N-bromophthalimide provided the electrophilic reagent, O,O-dimethyl-S-(N-phthalimido)phosphorothioate. Complementary methods based on these reagents enable the phosphorothiolation of diversely functionalized alkyl halides, arenediazonium salts, arylboronic acids and electron-rich arenes in good yields under mild conditions. (Figure presented.).
Preparation method of dialkoxyl phosphonothioate
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Paragraph 0035-0038, (2017/08/31)
The invention belongs to the technical field of organic synthesis and particularly discloses a preparation method of dialkoxyl phosphonothioate. The method comprises the steps of adding aryl sulfonyl chloride and dialkyl phosphite to an organic solvent, adding a copper salt catalyst and an L-proline ligand and reacting at 80-100 DEG C for 10-20h; and after reaction is completed, concentrating a reaction liquid, separating and purifying to obtain the dialkoxyl phosphonothioate. Cheap and available aryl sulfonyl chloride and dialkyl phosphite are taken as raw materials, an alkaline environment is not needed and a product is obtained only under the catalytic amount of copper salt and ligand. The substrate is wide in application range, simple in process, convenient to operate and wide in range, has relatively good productivity and is suitable for popularization and application; and the prepared product can be applied to multiple fields such as medicines and pesticides.
