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.
^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.
and 6 Related for: Hydrophosphonylation information
In chemistry hydrophosphonylation refers to any reaction where addition across a double bond generates a phosphonate (RP(O)(OR')2) group. Examples include...
MgBr(OH) Diethyl phosphite can add across unsaturated groups via a hydrophosphonylation reaction. For example, it adds to aldehydes in a manner similar to...
hydrolyse than phosphates. Aminophosphonates are often prepared by hydrophosphonylation, usually the condensation of imines and phosphorous acid. In the...
(RO)2P(O)H, adds across the carbon–nitrogen double bond of an imine (a hydrophosphonylation reaction). The reaction is closely related to the three-component...
Mannich reaction of the first two reagents). Decarboxylation of the hydrophosphonylation product gives the desired glyphosate product. Iminodiacetic acid...
enantioselective reactions including nitroaldol, Michael, Diels-Alder and hydrophosphonylation reactions. Their effectiveness arises in part from their ability...
Global Information