Abstract
Benzynes were selectively generated in-situ from phenols and trapped regioselectively by potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group to a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize using coupling reactions involving phenol derivatives with ammonia. While reactions of ortho - and meta -substituted phenols produced meta-substituted anilines exclusively, those of para -substituted phenols provided ortho -silylanilines.
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