Lithium amide zincate bases have been developed for the regioselective zincation of arenes and heteroarenes through directed metallation. Various transformations via the C–H zincation  have been explored including direct silylation and borylation as well as copper-catalyzed electrophilic amination with O-benzoyl hydroxylamines. These reactions occur under mild conditions for a broad scope of arenes and heteroarenes bearing simple common functionalities as directing groups, including amides, nitriles, methoxy, and halides. This C–H functionalization strategy provides rapid access from readily accessible starting materials to aromatic silanes and boronates as stable and useful synthetic precursors as well as aminoarenes as valuable common pharmaceutical targets.

C–H functionalization via lithium amide zincate base-mediated deprotonative zincation

255th National Meeting (2018)

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