Selective reductive cleavage of 2,3-epoxybromides by the InCl3–NaBH4 reagent system

A combination of sodium borohydride and a catalytic amount of indium(III) chloride in acetonitrile reduces 2,3-epoxybromides to the corresponding allylic alcohols in good yields involving reduction of the bromo moiety followed by selective C–O bond cleavage through a radical process. Several aromatic, cyclic and open-chain bromoepoxides successfully participated in this reaction.