A facile, high-yielding, one-step procedure is described for the preparation of a wide range of stable iminium salts by direct combination of an aldehyde or a ketone with a secondary free amine in the presence of an ammonium salt. The broad scope of the method is illustrated by the preparation of iminium ions derived from aldehydes, cyclic/acyclic ketones, and cyclic/acyclic secondary amines.
SabaS., BresciaA., and KaloustianM.K., Tetrahedron Lett., 1991, 32, 5031.
2.
SabaS., KojtariA., RiveraM.M., D'AmicoP., CanusoD., and KaloustianM. K., Abstracts, 37th Middle Atlantic, Regional Meeting of the American Chemical Society, New Brunswick, NJ, 2005, 710.
3.
RischN., and ArendM., Houben–Weyl, methods of organic chemistry, 4th edn., Thieme, Stuttgart, 1995. Vol. E21b, pp. 1881–1928.
4.
PaukstelisJ.V., Enamines, ed. CookA.G., Marcel Dekker, New York, 1988. pp. 276–334.
5.
BöhmeH., and VieheH.G., Iminium salts in organic chemistry, Part I, eds John Wiley & Sons, New York, 1976, Vol. 9.
6.
BöhmeH., and VieheH.G., Iminium salts in organic chemistry, Part II, eds John Wiley & Sons, New York, 1979, Vol. 9.
7.
TehraniK.A., and De KimpeN., Sci. Synth., 2004, 27, 313.