4184-51-4Relevant academic research and scientific papers
Validation of Arylphosphorothiolates as Convergent Substrates for Ar-SF 4Cl and Ar-SF 5Synthesis
Wang, Lin,Ni, Shengyang,Cornella, Josep
supporting information, p. 4308 - 4312 (2021/06/02)
In this manuscript we describe the oxidative fluorination of aryl phosphorothiolates to access Ar-SF4Cl compounds. These compounds serve as precursors for the highly coveted Ar-SF5 compounds. The use of phosphorothiolates as starting materials permits access to Ar-SF4Cl from a wide variety of available starting materials, namely boronic acids, diazonium salts, aryl iodides, thiophenols, or simple arenes. The protocol has been demonstrated for 10 examples and showed good tolerance to various functional groups. Finally, we demonstrated that AgBF4 can be used as a fluorinating agent, affording good yields of an Ar-SF5.
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.
Preparation method of dialkoxyl phosphonothioate
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Paragraph 0040-0043, (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.
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.
