Reductions and free radical cyclizations of alkyl- and aryl bromides are effected in aqueous base by NaBH4 in conjunction with a base-soluble dialkyltin(IV) reagent and 4,4′-azobis(4-cyanovaleric acid) (ACVA). The aryl bromides reduce at lower rates under tin-free conditions using simply NaBH4-ACVA.
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Rai et al. (1994) studied this question.
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