<i>N</i>-(diisopropylphosphanyl)benzamide

<i>N</i>-(diisopropylphosphanyl)benzamide, PhC(O)NHP<i>i</i>Pr<sub>2</sub>, has been synthesized in good yield following two alternative procedures that employ benzamide as the starting material. The first one is a two-step preparation, in which <i>N</i&g...

Full description

Bibliographic Details
Main Authors: María M. Alcaide, Daniel García Garrido, Eleuterio Álvarez, Riccardo Peloso
Format: Article
Language:English
Published: MDPI AG 2023-06-01
Series:Molbank
Subjects:
Online Access:https://www.mdpi.com/1422-8599/2023/2/M1667
Description
Summary:<i>N</i>-(diisopropylphosphanyl)benzamide, PhC(O)NHP<i>i</i>Pr<sub>2</sub>, has been synthesized in good yield following two alternative procedures that employ benzamide as the starting material. The first one is a two-step preparation, in which <i>N</i>-(trimetilsilyl)benzamide is reacted with P<i>i</i>Pr<sub>2</sub>Cl to give the title compound in good yield, whereas the second one is a straightforward synthesis which converts benzamide into <i>N</i>-(diisopropylphosphanyl)benzamide by reaction with P<i>i</i>Pr<sub>2</sub>Cl in the presence of <i>N,N</i>-dimethylpyridin-4-amine (DMAP) and triethylamine. NMR spectroscopy and X-ray diffraction analyses have been performed to characterize the new compound and elucidate its molecular structure in the solid state. <i>N</i>-(diisopropylphosphanyl)benzamide adds to the limited family of amido-substituted phosphines, RC(O)NHPR’<sub>2</sub>, which can be classified as bidentate hybrid P,O-ligands, both in their neutral and anionic forms, the latter achievable by deprotonation of the NH group.
ISSN:1422-8599