Kabachnik-Fields reaction

What is Kabachnik-Fields reaction?

The Kabachnik-Fields reaction, a one-pot synthesis of α-amino phosphonates via a three-component coupling of an aldehyde (or ketone), an amine, and a dialkylphosphite, was first reported concurrently in 1952 by Kabachnik and Medved and Fields.

Kabachnik-Fields reaction - general reaction scheme - Kabachnik-Fields synthesis
Kabachnik-Fields reaction

Kabachnik-Fields reaction is also known as the Kabachnik-Fields synthesis and is catalyzed by an acid or promoted by a base. Primary and secondary amines can undergo this reaction, although aliphatic ketones react more readily than aldehydes. Aromatic-aliphatic and alicyclic ketones react with amine at a slower rate, while aromatic ketones react with even more difficulty. The resulting α-amino phosphonates are useful for chelating agents.

Direct reaction between phosphonate and imine results in the same product as the three-component coupling from phosphite, amine, and carbonyl compound, and high yields are achieved if the anhydrous ammonia and carbonyl compounds are mixed before the dialkyl phosphite is added. The Kabachnik-Fields reaction can also be promoted by microwave.