A new, convenient and high-yielding procedure for the one-pot synthesis of diethyl a-aminophosphonates from aldehydes, amines and diethyl phosphite (Kabacknik-Fields reaction) in SDS micellar solution in aqueous media is described. The synthesis of aaminophosphonates in the present study represents a three-component reaction in which no intermediate formation of either an imine or a-hydroxyphosphonate was observed.Use of aqueous media as a reaction solvent has attracted much attention in synthetic organic chemistry for several reasons. 1 In comparison with organic solvents, water is cheap, safe, reduces the use of harmful organic solvents and leads to the development of environmentally friendly chemical processes. 2 In addition, reactions in aqueous media illustrate unique reactivities and selectivities that are not usually observed in organic media. 3 However, organic solvents are still used instead of water for mainly two reasons. First, most organic substrates are not soluble in water and, as a result, water cannot function as a reaction medium. Second, many reactive substrates, reagents and catalysts are sensitive towards water and are decomposed or deactivated in aqueous media. A possible way to improve the solubility of substrates is the use of surfaceactive reagents that can form micelles 4 or vesicular structures in aqueous media. Micelles are dynamic clusters of surfactant molecules which posses both hydrophilic and hydrophobic structures. 5 It is well established that, in many cases, the rates and pathways of many chemical reactions can be altered by performing the reactions in micellar media instead of pure bulk solvents. Micelles can concentrate the reactants within a small volume, stabilize substrates, intermediates or products and orient substrates so that ionization potential, oxidation-reduction properties, dissociation constants, physical properties and reactivities are changed. Thus, they can alter the reaction rate, mechanism, regio-and stereoselectivity of the reaction. 6
A new and convenient procedure has been developed for the one-pot synthesis of different types of primary 1-aminophosphonates from aldehydes/ketones, HMDS and diethyl phosphite using I 2 as an inexpensive, non-toxic, non-metallic and readily available catalyst. These reactions proceeded under solvent-free conditions and produced the desired products in high yields.
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