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
editSee also
edit- Hydrophosphination - the addition of a phosphine derivative (PHR2) across a double bond
References
edit- ^ 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.
- ^ 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.
- ^ 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.