A new and effective allylation protocol was developed for less reactive simple imines using diallyldibutyltin in the presence of a catalytic amount of In(OTf)3. Allyltin reagents were reacted with imines in dichloromethane under 10 mol% In(OTf)3 without any other additives, to form homoallylic amines in moderate to good yields (80%～90%). In addition, a series of aldimines could be reacted with tetraallyltin in a 2∶1 molar ratio catalyzed by In(OTf)3 (10 mol%) to afford the corresponding products in good yields. A probable mechanistic pathway to explain the allylation process was depicted.

Key words: In(OTf)3, allylation, imine, diallyldibutyltin, tetraallyltin