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The allylic-type diindium reagents A and B were prepared from 3-bromo-1-iodopropene (1a) and 4-bromo-2-iodobut-2-ene (1b), respectively, and their reactions with electrophiles were investigated. The diindium reagents A and B were initially reacted with imines and the resulting vinylindium compounds were then treated with organic halides in the presence of Pd(PPh(3))(4) to give linear N-aryl and N-tosyl homoallylic amines. Diindium A is stable in a small amount of water in solvent, whereas B is easily protonated to give a crotylindium reagent. The reaction of B with benzaldehyde gives mainly the 1,3- and 1,5-diols via a spontaneous coupling with two molecules of the aldehyde, in contrast to A, which reacts with one molecule of carbonyl compounds to give the vinylindium compounds.

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Allylic-type diindium reagents were prepared from 3-bromo-1-iodopropene (1a), 3-bromo-1-iodo-1-phenylpropene (1b), or 2,4-diiodobut-2-en-1-ol (1c) with metallic indium, and their successive coupling with electrophiles was examined. The coupling behavior of the diindium reagents was found to depend on the electrophiles and the substituent on the diindium compounds.

Allylic-Type Diindium Reagents. Reactivity Toward Electrophiles and CascadeCoupling Reactions with Imines. -The reaction of the allylic-type diindium reagents generated from the halides (I) and (V) with electrophiles is studied. They show different behavior toward water and aldehydes. For example, the diindium reagent resulting from (V) smoothly reacts with two molecules of aldehydes to afford diols, whereas the diindium reagent from (I) only reacts with one molecule of aldehyde. The cascade coupling with imines and allyl halides provides a versatile route to linear homoallylic amines. -(HIRASHITA*, T.; HAYASHI, Y.; MITSUI, K.; ARAKI, S.;