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The formation of a mixture of both o- and m-iodinated products is most likely due to an electrophilic substitution. The lack of reactivity of the N-methyl group in 17 could be explained by a bisdentate coordination from the Boc and the electron-rich aryl ring, which positions the N-methyl group away from the Pd(II) center. The presence of a p-methyl group also inhibits the N-methyl oxidation.
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