A mixture of iodine and CuO·HBF4 reacts stereoselectively with alkenes in the presence of a wide variety of nucleophiles (water, MeOH, HCO2H, AcOH, EtCO2H, NaNO2, KSCN, NaSO2Ar, LiCl, LiBr, Nal, Et3SiH, and MeOPh) to give the corresponding 2-functionalized iodo compounds. A regio-chemistry study is also reported.
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Barluenga et al. (1990) studied this question.
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