article · Synthetic Communications
Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R<sub>F</sub>O)<sub>2</sub>P(O)NHR (R = CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>3</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>4</sub>-CH<sub>3</sub>, CH(CH<sub>3</sub>)<sub>2</sub>, C<sub>6</sub>H<sub>11</sub>, CH<sub>2</sub>CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub>, CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub> or C<sub>6</sub>H<sub>5</sub>; R<sub>F</sub> = CH<sub>2</sub>CF<sub>3</sub>, CH<sub>2</sub>C<sub>2</sub>F<sub>5</sub> or CH<sub>2</sub>CH<sub>2</sub>C<sub>6</sub>F<sub>13</sub>) 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 H<sub>2</sub>O<sub>2.</sub>This method was chosen out of various literature common methods, which were thoroughly investigated using <sup>31</sup>P 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 (<sup>1</sup>H,<sup>13</sup>C,<sup>31</sup>P, and <sup>19</sup>F) NMR, IR, and HRMS techniques.
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DOI: 10.1080/00397911.2024.2382784
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