In chemistry hydrophosphonylation refers to any reaction where
addition
Addition (usually signified by the Plus and minus signs#Plus sign, plus symbol ) is one of the four basic Operation (mathematics), operations of arithmetic, the other three being subtraction, multiplication and Division (mathematics), division. ...
across a
double bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...
generates a
phosphonate
In organic chemistry, phosphonates or phosphonic acids are organophosphorus compounds containing groups (where R = alkyl, aryl, or just hydrogen). Phosphonic acids, typically handled as salts, are generally nonvolatile solids that are poorly ...
(RP(O)(OR')
2) group. Examples include the Kabachnik–Fields reaction, where a dialkyl
phosphite
The general structure of a phosphite ester showing the lone pairs on the P
In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. They can be considered as esters of a ...
reacts across an
imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bo ...
to form an
aminophosphonate Aminophosphonates are organophosphorus compounds with the formula (RO)2P(O)CR'2NR"2. These compounds are structural analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups. Acting as antagonists of a ...
. The reaction is catalyzed by bases and is subject to
organocatalysis
In organic chemistry, organocatalysis is a form of catalysis in which the rate of a chemical reaction is increased by an organic catalyst. This "organocatalyst" consists of carbon, hydrogen, sulfur and other nonmetal elements found in organic com ...
.
Important compounds generated by this reaction include the common herbicide
glyphosate
Glyphosate (IUPAC name: ''N''-(phosphonomethyl)glycine) is a broad-spectrum Herbicide, systemic herbicide and Crop desiccation, crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plan ...
.
:
Hydrophosphonylation reactions
*
Kabachnik–Fields reaction In organophosphorus chemistry, the Kabachnik–Fields reaction is a three-component organic reaction forming aminophosphonate, α-aminomethylphosphonates from an amine, a carbonyl compound, and a phosphite ester, dialkyl phosphonate, (RO)2P(O)H (tha ...
*
Pudovik reaction In organophosphorus chemistry, the Pudovik reaction is a method for preparing α-aminomethylphosphonates. Under basic conditions, the phosphorus–hydrogen bond of a dialkylphosphite, (RO)2P(O)H, adds across the carbon–nitrogen double b ...
*
Abramov reaction
See also
*
Hydrophosphination
Hydrophosphination is the insertion of a double bond, carbon-carbon multiple bond into a phosphorus-hydrogen bond forming a new phosphorus-carbon bond. Like other hydrofunctionalizations, the rate and regiochemistry of the insertion reaction is in ...
- the addition of a phosphine derivative (PHR
2) across a double bond
References
{{Reflist
Addition reactions