Water promoted general and practical addition of amines to acrylic acid derivatives and vinyl sulfones

A simple, efficient, versatile, general and practical strategy has been developed for the addition of a variety of aryl and alkylamines to activated olefins; acrylonitrile, acrylamide, N,N-methylenebisacrylamide, divinyl sulfone, phenyl vinyl sulfone and ethyl vinyl sulfone promoted by water carried out at a temperature of 100 °C, or at room temperature in few cases, giving rise to the corresponding β-amino derivatives in good to excellent yields. Addition of electron rich primary arylamines including aniline as well as aliphatic amines to divinyl sulfone carried out at room temperature furnished N-aryl/alkyl thiomorpholine-1,1-dioxides by a double Michael addition, but ortho substituted anilines did not show selectivity toward N-aryl thiomorpholine-1,1-dioxides as they also gave the bisadducts or monoadducts due to the steric effect exerted by the ortho substituent. Selectivity to the more thermodynamically controlled product, N-aryl thiomorpholine-1,1-dioxides could be achieved in these cases when the reactions were carried out at 100 °C.