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1.2.1.9 Third Component Phosphonate (Kabachnik–Fields Reaction)

DOI: 10.1055/sos-SD-210-00157

Zefirov, N. S.; Matveeva, E. D.; Shuvalov, M. V.Science of Synthesis: Multicomponent Reactions, (20141273.

General Introduction

Following the work of Arbuzov, the Kazan State University became one of the recognized centers of organophosphorus chemistry research. The period 1950–1955 was very fruitful for the discovery of novel addition reactions of P—H bond-containing compounds across unsaturated bonds of different types. Firstly, it was discovered in 1950 that addition of dialkyl phosphonates to CO bonds proceeds to give α-hydroxy phosphonates (Abramov reaction; Scheme 1).[‌1‌,‌2‌] Secondly, the addition of compounds containing a P—H bond to the CN bond of imines, giving α-amino phosphonates, was reported in 1952 (Pudovik reaction; Scheme 1).[‌3‌] However, probably the most remarkable reaction, also leading to the synthesis of α-amino phosphonates, was that discovered by Kabachnik[‌4‌,‌5‌] and Fields[‌6‌] in 1952 (Kabachnik–Fields reaction), a one-pot, three-component operation using a carbonyl compound, an amine, and a dialkyl phosphonate (Scheme 1). The discovery of this process occurred at a time when multicomponent processes were considered to be rather “exotic birds”. From a modern viewpoint, this protocol is very attractive for application in combinatorial chemistry, and has occasionally been used in parallel synthesis.[‌7‌]

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References