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Hydrophosphonylation

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In chemistry hydrophosphonylation refers to any reaction where addition across a double bond generates a phosphonate (RP(O)(OR')2) group. 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. Important compounds generated by this reaction include the common herbicide glyphosate.

Kabachnik-Fields Reaction

Hydrophosphonylation reactions

See also

References

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