Silica gel and polystyrene supported aluminum chloride as heterogeneous catalysts for the preparation of α‐aminophosphonates

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

“…1 H, 13 C, and 31 P NMR spectra were taken on Bruker avance 500 MHz spectrometer in CDCl 3 using TMS as internal standard. 31 P NMR (202.44 MHz) was taken in CDCl 3 using 85% H 3 PO 4 as external standard with broadband 1 H decoupling.…”

“…[5][6][7][8][9][10] Furthermore, α-aminophosphonates are used in agricultural industry as fungicidal, herbicidal agents, and plant growth regulators. [11][12][13] Consequently, different methods have been developed for their synthesis. Among them, nucleophilic addition of phosphites to imines is an established most useful method in which catalysts like InCl 3 , SnCl 4 , amberlite-IR 120, sulfamic acid, TiO 2 , In(OTf) 3 , Silica sulphuric acid, Al(H 2 PO 4 ) 3 , Mg(ClO 4 ) 2 , TaCl 5 -SiO 2 , bismuth nitrate penta hydrate, and lithium perchlorate [14][15][16][17][18][19][20][21][22][23][24][25] are conveniently used.…”

A Critical Overview of the Kabachnik-Fields Reactions Utilizing Trialkyl Phosphites in Water as the Reaction Medium: A Study of the Benzaldehyde-Benzylamine Triethyl Phosphite/Diethyl Phosphite Models

“…A lot of variations were elaborated during the past decades using different model compounds and applying different conditions. A great number of catalyst were described that made possible carrying out the reactions under mild conditions , including microwave (MW)‐assisted and solvent‐free accomplishments . However, it was found by the senior author of this article that, in most cases, there is no need to use any catalyst, as the Kabachnik–Fields reaction takes place efficiently under catalyst‐ and solvent‐free conditions on MW irradiation .…”

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

“…Additionally, it is a water-tolerant entity that can act as Brønsted or Lewis acid in the presence of water. 29 Therefore, in connection with our program concerning to the synthesis of α-aminophosphonates, [20][21][22][23][24][25][26][27][28][29][30][31][32][33] we now report for the first time an operationally simple, expeditious solvent-free synthesis of several tertiary and quaternary α-aminophosphonates using commercially available PhB(OH) 2 as catalyst at 50°C (Scheme 1). The versatility of this catalyst was exploited by us obtaining the α-aminophosphonates with moderated to excellent yields in very short reaction times.…”

“…6,9 For this reason, the synthesis of α-aminophosphonates has received considerable attention, and significant progress has been made to develop more efficient methods for the preparation of these compounds. [18][19][20] In this context, the one-pot, three-component reaction between an aldehyde, an amine, and di-or trialkyl phosphite catalyzed by different Lewis or Brønsted acids, [21][22][23][24][25][26][27] is one of the most useful methods for the synthesis of α-aminophosphonates due to its versatility and high yields. In recent years, several catalysts have been designed and employed for this reaction; however, in spite of their potential utility, these procedures typically suffer from one or more disadvantages such as the use of expensive and stoichiometric amount of catalyst, specialized handling techniques and tedious workup are necessary, long reaction time, vigorous reaction conditions, requirement of excess of reagents, use of solvent, unsatisfactory yield, and lack of generality.…”