Phenylboronic Acid as Efficient and Eco-Friendly Catalyst for the One-Pot, Three-Component Synthesis of α-Aminophosphonates under Solvent-Free Conditions

Abstract

A simple, mild, and efficient one-pot, three-component synthetic method has been developed for the preparation of α-aminophosphonates using phenylboronic acid as catalyst under solventfree conditions at 50°C. The process involves the reaction of carbonyl compounds (aldehydes or ketones) with benzylamine and dimethyl phosphite. A wide range of carbonyl compounds are compatible with this reaction, producing tertiary and quaternary αaminophosphonates in moderated to excellent yields in short time.

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

“…An efficient method was developed for the preparation of α-aminophosphonates ( 26 ), which involved applying phenylboronic acid as the catalyst under solvent-free conditions at 50 °C ( Scheme 21 ) [ 44 ].…”

Catalyst‐Free Three‐Component Synthesis of α‐Amino Phosphonates

“…[37] In 2012, Mario Ordóñez et al developed a one-pot, three-component synthesis of α-amino phosphonates under solvent-free conditions using phenylboronic acid as an efficient and eco-friendly catalyst. [38] In 2014, the same group reported phenyl phosphonic acid as an efficient and recyclable catalyst in the synthesis of α-amino phosphonates under solvent-free conditions. [39] In 2017, Keglevich et al reported a microwave-assisted Pudovik reaction for the synthesis of α-aryl-α-amino phosphonates and α-aryl-αamino phosphine oxides.…”

“…In 2012, Mario Ordóñez et al . developed a one‐pot, three‐component synthesis of α‐amino phosphonates under solvent‐free conditions using phenylboronic acid as an efficient and eco‐friendly catalyst [38] . In 2014, the same group reported phenyl phosphonic acid as an efficient and recyclable catalyst in the synthesis of α‐amino phosphonates under solvent‐free conditions [39] .…”

N-Functionalization of β-aminophosphonates: cytotoxic effects of the new derivatives

“…According to the approach of Kirilov and Petrova, carbanions generated from phosphonates were added to the CvN double bond of imines. [20][21][22][23][24][25][26] Last but not least, catalytic hydrogenation of β-iminophosphonates [27][28][29][30] and β-nitrophosphonates [31][32][33] may also be a suitable method for the preparation of β-aminophosphonates. α,β-Diaminophosphonates were also described as promising new targets.…”