Application of Lanthanoid Catalysts for the Synthesis of Michler's Hydride

Andrews, Philip C.; Junk, Peter C.; Kemppinen, K. Peter; Konstas, Kristina; Tuck, Kellie L.
April 2009
Letters in Organic Chemistry;Apr2009, Vol. 6 Issue 3, p229
Academic Journal
A series of lanthanoid (Ln3+) based Lewis acid catalysts were investigated as alternatives to other metal based catalysts for the formation of Michler's hydride, 4,4'-methylenebis(N,N-dimethylaniline) (1). The lanthanoid based Lewis acid catalysts were superior to previously published catalysts resulting in formation of 4,4'- methylenebis(N,N-dimethylaniline) (1) and N,N-dimethyl-4-(4-(methylamino)benzyl)aniline (2). If paraformaldehyde was added to the reaction only 4,4'-methylenebis(N,N-dimethylaniline) (1) was formed.


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