A mixture of iodine and CuO·HBF4 reacts stereospecifically with olefins in the presence of a wide variety of nucleophiles (NaNO2, NaSO2Ar, Nal, Et3SiH, MeOPh and H2O) to give the corresponding 2-functionalized iodo compounds; the same reagents also cause iodofunctionalization of 1,3-dienes and acetylenes.
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Barluenga et al. (1987) studied this question.