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

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,Ndimethylaniline) (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.