4163-76-2Relevant academic research and scientific papers
Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations
Kovács, Szabolcs,Bayarmagnai, Bilguun,Aillerie, Alexandre,Goo?en, Lukas J.
supporting information, 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.).
A S-aryl thiophosphate preparation method
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Paragraph 0107-0111, (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.
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.
