Tween-20: An Efficient Catalyst for One-Pot Synthesis of α-Aminophosphonates in Aqueous Media

Abstract

A green one-pot three-component synthesis has been developed for α-aminophosphonates by condensation of aldehydes, amines, and diethylphosphite by using nonionic surfactant Tween-20 as catalyst in aqueous media. The results showed that this synthetic route for α-aminophosphonates takes just 25-60 min for completion at 60 • C and affords 64%-91% yields depending on the nature of the amine substrates. The major advantages of this novel method are green reaction conditions with water as solvent, simple workup, less reaction times, and high to moderate yields.

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

“…The nonionic surfactant Tween-20 (polyoxyethylene derivative of sorbitan monolaurate; Sorbitan-20; Fig. 1) was also used under environmentally friendly conditions for the one-pot, three-component synthesis of aminophosphonates [30]. The major advantages were claimed to be the wide scope of substrates, simple work-up, short reaction time (ca 30 min), and high yields.…”

Environmentally Benign Syntheses of α-Substituted Phosphonates: Preparation of α-Amino- and α-Hydroxyphosphonates in Water, in Ionic Liquids, and under­ Solvent-Free Conditions

“…Another successful example of the use of surfactant in the synthesis of α-aminophosphonates was reported by Sundar et al, 33 who employed the commonly used anionic surfactant polyoxyethylene(20)sorbitan monolaurate, sold under the commercial brand Tween-20. This surfactant is used as a catalyst, emulsifier, and complexing agent in both aqueous and nonaqueous media.…”

Clean Procedure for the Synthesis of Α-Aminophosphonates Catalyzed by Choline-Based Ionic Liquid

“…The reaction proceeds via the imine formed from carbonyl compounds and amines, which then converted to the corresponding aminophosphonates by the reaction with triethyl phosphite or diethyl phosphite . Many efforts have been made to develop efficient methods for the synthesis of α‐aminophosphonates, including the one‐pot multicomponent reaction (MCR)of aldehydes, amines, and triethyl phosphite/diethyl phosphite, catalyzed by Lewis/Brønsted acids , solid acids , surfactants , metal salts , or metal oxides . Many of these works used one kind of P‐reagents, triethyl phosphite, or diethyl phosphite, respectively, though a fewer used both of P‐reagents [4a].…”