A variety of difunctionalized aryl-2-oxazolines were prepared from the reaction of halophenyl-2-oxazolines and TMPMgCl·LiCl to give an organomagnesium reagent, which was then treated with various electrophiles. The metalation step takes place under mild conditions, and this process al-

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We have prepared novel highly functionalized benzene derivatives by regioselective metalation of ester-, amide-, carbamate-, and carbonate-substituted 2-phenyl-2-oxazolines with mixed lithium−magnesium amides followed by reaction with different electrophiles. While a complementary metalation site can be accessed by using different bases, steric and electronic effects promoted by the aromatic ring substituents also play an important role in reaction regioselectivity. Computational calculations of the aromatic hydrogen pK a values have helped us to rationalize the metalation preference by the complex-induced proximity effect concept.

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