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  • Title: Allylic-type diindium reagents. Reactivity toward electrophiles and cascade coupling reactions with imines.
    Author: Hirashita T, Hayashi Y, Mitsui K, Araki S.
    Journal: J Org Chem; 2003 Feb 21; 68(4):1309-13. PubMed ID: 12585869.
    Abstract:
    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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