31003-27-7Relevant articles and documents
Phenylphosphonic acid as efficient and recyclable catalyst in the synthesis of α-aminophosphonates under solvent-free conditions
Bedolla-Medrano, Mercedes,Hernández-Fernández, Eugenio,Ordó?ez, Mario
, p. 1145 - 1149 (2014/05/20)
Phenylphosphonic acid is an efficient, friendly and reusable heterogeneous catalyst for the synthesis of α-aminophosphonates through a 'one-pot' three-component reaction of amines, carbonyl compounds and dialkyl phosphites under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines, aliphatic and aromatic aldehydes and aliphatic ketones. It also enabled the synthesis of α-aminophosphonates in large scale, clean conversion, easy workup and purification. Excellent results were obtained in each case obtaining the desire compounds in moderate to good yields. Georg Thieme Verlag Stuttgart New York.
Phenylboronic acid as efficient and eco-friendly catalyst for the one-pot, three-component synthesis of α-aminophosphonates under solvent-free conditions
Tibhe, Gaurao D.,Bedolla-Medrano, Mercedes,Cativiela, Carlos,Ordó?ez, Mario
supporting information; experimental part, p. 1931 - 1936 (2012/09/22)
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 solvent-free 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 α-aminophosphonates in moderated to excellent yields in short time. Georg Thieme Verlag Stuttgart · New York.
An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate
Bhagat, Srikant,Chakraborti, Asit K.
, p. 1263 - 1270 (2007/10/03)
(Chemical Equation Presented) Commercially available magnesium perchlorate is reported as an extremely efficient catalyst for the synthesis of α-aminophosphonates. A three-component reaction (3-CR) of an amine, an aldehyde or a ketone, and a di-/trialkyl phosphite (Kabachnik-Fields reaction) took place in one pot under solvent-free conditions to afford the corresponding α-aminophosphonates in high yields and short times. The use of solvent retards the rate of the reaction and requires a much longer reaction time than that for neat conditions. The reactions involving an aldehyde, an aromatic amine without any electron-withdrawing substituent, and a phosphite are carried out at rt. The reactions involving cyclic ketones, aromatic amines with an electron-withdrawing substituent, and aryl alkyl ketone (e.g., acetophenone) require longer reaction times at rt or heating. Magnesium perchlorate was found to be superior to other metal perchlorates and metal triflates during the reaction of 4-methoxybenzaldehyde, 2,4-dinitroaniline, and dimethyl phosphite. The catalytic activity of various magnesium compounds was influenced by the counteranion, and magnesium perchlorate was found to be the most effective. The reaction was found to be general with di-/trialkyl phosphites and diaryl phosphite. The Mg(ClO4)2-catalyzed α- aminophosphonate synthesis in the present study perhaps represents a true three-component reaction as no intermediate formation of either an imine or α-hydroxy phosphonate was observed that indicated the simultaneous involvement of the carbonyl compound, the amine, and the phosphite in the transition state.
