Kabachnik–Fields reaction: Difference between revisions
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In [[organophosphorus chemistry]], the '''Kabachnik–Fields reaction''' is a three-component [[organic reaction]] forming an α-[[amino]] [[phosphonate]] from an [[amine]], a [[carbonyl]] compound, and a [[diethylphosphite|dialkyl phosphonate]] ((RO)<sub>2</sub>P(O)H).<ref>{{cite journal|title=The Kabachnik-Fields reaction: mechanism and synthetic use|authors=Keglevich, Gyorgy; Balint, Erika|journal=Molecules|year=2012|volume=17|pages=12821-12835|doi=10.3390/molecules171112821}}</ref> Aminophosphonates are synthetic targets of some importance as [[phosphorus]] analogues of α-[[amino acid]]s (a [[bioisosterism|bioisostere]]). This [[multicomponent reaction]] was independently discovered by Martin Izrailevich Kabachnik<ref>{{cite journal| last=Kabachnik | first=Martin I. |author2=T. Ya. Medved | year=1952 | title=Новый метод синтеза сс-аминофосфиновых кислот | trans_title=<!-- A new method for the synthesis of α-amino ? acids --> | journal=[[Doklady Akademii Nauk SSSR]] | volume=83 | page=689}}</ref> and Ellis K. Fields<ref>{{cite journal| last=Fields | first=Ellis K. | year=1952 | title=The synthesis of esters of substituted amino phosphonic acids | journal=[[Journal of the American Chemical Society]] | volume=74 | issue=6 | pages=1528–1531 | doi=10.1021/ja01126a054}}</ref> in 1952. The reaction is very similar to the two-component [[ Pudovik reaction]], which involves condensation of the phosphite and a preformed imine. |
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:[[Image:Kabachnik-Fields Reaction.svg|Kabachnik-Fields Reaction]] |
:[[Image:Kabachnik-Fields Reaction.svg|Kabachnik-Fields Reaction]] |
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The first step in this reaction is the formation of an [[imine]] followed by an [[addition reaction]] of the phosphonate P-H bond |
The first step in this reaction is the formation of an [[imine]] followed by an [[addition reaction|addition]] of the phosphonate P-H bond across the C=N double bond.<ref>{{cite journal| last=Zefirov | first=Nikolay S. |author2=Elena D. Matveeva | date=2008-01-18 | title=Catalytic Kabachnik-Fields reaction: New horizons for old reaction | journal=[[ARKIVOC]] | volume=2008 | issue=i | pages=1–17 | url=http://www.arkat-usa.org/get-file/22930/?wikipedia-format=.pdf | accessdate=2009-12-08 | doi=10.3998/ark.5550190.0009.101}}</ref> A related reaction is the [[Mannich reaction]]. |
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The reaction is accelerated with a combination of dehydrating reagent and [[Lewis acid]]. The carbonyl component in the reaction is usually an [[aldehyde]] and sometimes a [[ketone]]. |
The reaction is accelerated with a combination of dehydrating reagent and [[Lewis acid]]. The carbonyl component in the reaction is usually an [[aldehyde]] and sometimes a [[ketone]]. |
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Revision as of 01:01, 10 July 2017
In organophosphorus chemistry, the Kabachnik–Fields reaction is a three-component organic reaction forming an α-amino phosphonate from an amine, a carbonyl compound, and a dialkyl phosphonate ((RO)2P(O)H).[1] Aminophosphonates are synthetic targets of some importance as phosphorus analogues of α-amino acids (a bioisostere). This multicomponent reaction was independently discovered by Martin Izrailevich Kabachnik[2] and Ellis K. Fields[3] in 1952. The reaction is very similar to the two-component Pudovik reaction, which involves condensation of the phosphite and a preformed imine.
The first step in this reaction is the formation of an imine followed by an addition of the phosphonate P-H bond across the C=N double bond.[4] A related reaction is the Mannich reaction.
The reaction is accelerated with a combination of dehydrating reagent and Lewis acid. The carbonyl component in the reaction is usually an aldehyde and sometimes a ketone.
References
- ^ "The Kabachnik-Fields reaction: mechanism and synthetic use". Molecules. 17: 12821–12835. 2012. doi:10.3390/molecules171112821.
{{cite journal}}: Unknown parameter|authors=ignored (help)CS1 maint: unflagged free DOI (link) - ^ Kabachnik, Martin I.; T. Ya. Medved (1952). "Новый метод синтеза сс-аминофосфиновых кислот". Doklady Akademii Nauk SSSR. 83: 689.
{{cite journal}}: Cite has empty unknown parameter:|trans_title=(help) - ^ Fields, Ellis K. (1952). "The synthesis of esters of substituted amino phosphonic acids". Journal of the American Chemical Society. 74 (6): 1528–1531. doi:10.1021/ja01126a054.
- ^ Zefirov, Nikolay S.; Elena D. Matveeva (2008-01-18). "Catalytic Kabachnik-Fields reaction: New horizons for old reaction" (PDF). ARKIVOC. 2008 (i): 1–17. doi:10.3998/ark.5550190.0009.101. Retrieved 2009-12-08.