Indium-mediated reaction of 1,3-dichloropropene with aldehyde gave syn-chlorohydrin predominantly. A similar reaction of 1,3-dibromopropene gave viayloxirane and homoallyl alcohol; the former is formed from γ-bromoallylindium via the corresponding bromohydrin, and the latter is considered to be derived from a unique allylic diindium reagent, 3,3-diindiopropene.
transmetalation of the pi-allylpalladium(II) complexes, generated in situ from a catalytic amount of a palladium(0) complex and a variety of allylic substrates, with indium(I) salts proceeded smoothly in various solvents, providing a new route for allylindium(III) reagents.
The reaction of 1,3-dibromopropene with carbonyl compounds mediated by indium in water gave bis-allylation products connected to the same carbon. Such a reactivity effectively constitutes a gem-allyldianionsynthon.