The processes of p-bromination and p-iodination have been known for decades. Most approaches for p-iodination have used I2 or NIS as the halogen source whereas a much wider array of reagents have been used for the source of p-brominations. In this study, utilizing only NBS and I2 as the most convenient sources of the respective halogens and media containing no oxidants, acids or metals whatsoever, the below rapid transformations can be realized. As our approach utilizes only the combination of substrate, halogenating reagent and media, the effect of o- and m- R substituents providing perturbing secondary electronic process can be identified and compared. In general, mildly perturbing electron donating R substituents enhance reactivity while modest withdrawing substituents decrease reactivity.

Regiospecific p-brominations and p-iodinations: Perturbing secondary electronic effects

254th National Meeting (2017)

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