Efficient Synthesis of Phosphonamidates through One‐Pot Sequential Reactions of Phosphonites with Iodine and Amines

Abstract

Ao ne-pot sequential strategy to constructp hosphonamidates has been developed by generating phosphonites in situ from arylmagnesium bromides and triethyl phosphite followed by treatment with iodine and amines. A variety of phosphonamidatesw ere obtainedw ith good to excellent yields at room temperature from easily available materials.

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

“…Yugandhar and Srivastva [179] reported an efficient one‐pot synthesis of azaspiro[4.5]trienones 189 from aldehydes, substituted p ‐anisidines, isocyanides and 3‐aryl/alkyl propiolic acids (Scheme 101). This protocol involves a four‐component Ugi reaction and electrophilic ipso‐iodocyclization.…”

Visible Light Driven Oxidative Coupling of Amines and P(O)−H/P−OR Compounds under Photocatalyst‐Free Conditions

“…introduced a convenient, mild and high efficient way to synthesize phosphoramidates from iodine, amine and trialkyl phosphite [15a] . During our preparation of this manuscript, a sequential Grignard reagents participated, I 2 mediated coupling of phosphonites with amines [15b] was reported from the same group (Scheme 1c).…”

Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides

“…In the case of Staudinger-phosphonite synthesis, the necessary phosphonite and/or azide reagents need to be synthesized in advance, which comes with inherent safety risks and/or synthetic difficulties. Alternatives, such as the Atherton-Todd reaction, usually share these disadvantages [1]. Therefore, examples of the synthesis of amino acid-based phosphonamidates in the literature are mostly based on the so-called 'classical' approach, consisting of the monochlorination of a phosphonate ester, which is available through a Michaelis-Arbuzov reaction or Hirao coupling, followed by substitution with the desired nucleophile.…”