Indium-catalyzed allylation of imines with electrochemically assisted catalyst regeneration

The chemo-electrochemical regeneration of low valent indium(I) reagents for Barbier-type carboncarbon bond formation processes is described for several CN double bond systems. The homoallylic amines are obtained in good yields from aniline-derived aldimines. However, with ketimines and electron-poor aldimines, direct electrochemical or chemical reduction becomes a competing side reaction. Thus, hydrazones and sulfonimines gave almost exclusively the reduced products with only minor amounts of the allylated products being formed.