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Catalyst free, one pot synthesis of phosphoramidates under environment friendly conditions
Bashir Ahmad Dar 한국공업화학회 2016 Journal of Industrial and Engineering Chemistry Vol.36 No.-
An efficient and mild one pot synthesis of phosphoramidates has been reported from simple azideprecursors like benzyl, allyl and propargyl halides. The method is simple, metal free giving products ingood to excellent yields with wide substrate scope. Benzyl halide derivatives (Y–C6H4–CH2–X: X = Cl, Br;Y = p-F, Br, NO2 & o-Cl, NO2) reacted with NaN3 and P(OR’)3 at room temperature gave the correspondingphosphoramidates in 86–96% yields, while the reaction with allyl halides (R1,R2C = CH–CH2–X: X = Cl,Br, R1 & R2 = H, Me) in 60–73% yields. In polar solvents like DMF, DMSO, THF, acetonitrile, methanolmoderate yields were obtained (60%–67%) with incomplete substrate conversion. Yields were better inbinary polar solvents and water–ethanol was found to be the optimum green solvent in which upto 96%yield was obtained within 4.5 h. It was also observed that triethylphosphite showed better reactivitythan trimethylphosphite. Secondary and tertiary halides did not react at all under the optimizedconditions. This is the first catalyst free method for the one pot synthesis of phosphoramidates whichoffers significant green advantages like avoids hazardous organic azides, use of environment friendlyethanol and water as a green reaction medium.
Bashir Ahmad Dar,Meena Sharma,Baldev Singh,Arup Chakraborty,Parduman R. Sharma,Varsha Shrivastava,Amrita Bhowmik,Dushyant Vyas,Prince Bhatti 한국공업화학회 2013 Journal of Industrial and Engineering Chemistry Vol.19 No.3
An easy to prepare aluminium pillared interlayered clay (PILC) has been developed as a stable, recyclable and heterogeneous catalyst to promote the one-pot three component synthesis of a-aminophosphonates under solvent-free conditions using grindstone chemistry. Utilization of mild reaction conditions, clean conversion and greater selectivity under grinding conditions along with effortless separation, and purification of reaction products make this process extra attractive.