Hydrophosphonylation Explained

In chemistry hydrophosphonylation refers to any reaction where addition across a double bond generates a phosphonate (RP(O)(OR')₂) group.^[1] Examples include the Kabachnik–Fields reaction, where a dialkylphosphite reacts across an imine to form an aminophosphonate. The reaction is catalyzed by bases and is subject to organocatalysis.^{[2] [3]} Important compounds generated by this reaction include the common herbicide glyphosate.

Hydrophosphonylation reactions

• Kabachnik–Fields reaction
• Pudovik reaction
• Abramov reaction

See also

• Hydrophosphination - the addition of a phosphine derivative (PHR₂) across a double bond

Notes and References

1. Pudovik . A. N. . Konovalova . I. V. . Addition Reactions of Esters of Phosphorus(III) Acids with Unsaturated Systems . Synthesis . 1979 . 1979 . 2 . 81–96 . 10.1055/s-1979-28566.
2. Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines. Advanced Synthesis and Catalysis. Pedro Merino . Eugenia Marqués‐López . Raquel P. Herrera . 2008. 350. 9 . 1195–1208. 10.1002/adsc.200800131. 10261/114023. free.
3. Org. Synth.. 2017. 94. 313–331. 10.15227/orgsyn.094.0313. Catalytic Enantioselective Addition of Diethyl Phosphite to N-Thiophosphinoyl Ketimines: Preparation of (R)-Diethyl (1-Amino-1-phenylethyl)phosphonate. Shaoquan Lin . Yasunari Otsuka . Liang Yin . Naoya Kumagai . Masakatsu Shibasaki . free.