Synthesis and characterization of new highly fluorinated phosphoramidates bearing different alkylamino groups

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2024-08-02 DOI:10.1080/00397911.2024.2382784

Samar Argoubi , M. A. Sanhoury , I. Zerough , E. Manoury , I. Chehidi

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Abstract

Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R_FO)₂P(O)NHR (R = CH₂CH₂CH₃, (CH₂)₃CH₃, (CH₂)₄-CH₃, CH(CH₃)₂, C₆H₁₁, CH₂CH₂-C₆H₅, CH₂-C₆H₅ or C₆H₅; R_F = CH₂CF₃, CH₂C₂F₅ or CH₂CH₂C₆F₁₃) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H₂O_2.This method was chosen out of various literature common methods, which were thoroughly investigated using ³¹P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (¹H,¹³C,³¹P, and ¹⁹F) NMR, IR, and HRMS techniques.

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带有不同烷基氨基的新型高氟化磷酰胺的合成与表征

合成了 17 种新的含烷基氨基的(RFO)2P(O)NHR（R = CH2CH2CH3、(CH2)3CH3、(CH2)4-CH3、CH(CH3)2、C6H11、CH2CH2-C6H5、CH2-C6H5 或 C6H5；RF = CH2CF3、CH2C2F5 或 CH2CH2C6F13）高氟化磷酰胺。这些化合物是以分子碘作为温和的催化剂，在 H2O2 的存在下，通过伯胺与作为磷酸化剂的双（多氟烷基）亚磷酸酯反应而得到的。此外，还研究了不同膦酸盐反应速率的变化，并与之前的研究成果进行了比较。利用多核（1H、13C、31P 和 19F）核磁共振、红外和 HRMS 技术对标题磷酰胺进行了全面表征。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.