Abstract
AbstractThe detailed mechanism and origins of gold‐catalyzed intramolecular dearomatization of naphthols to spirocarbocycles are systematically studied. Specifically, the hydrogen‐bonding mediated cooperative Brønsted‐acid catalysis mechanism was the most plausible mechanism for dearomatization to spirocarbocycles because of its intricate interplay between hydrogen bonds and conjugated π systems in the spirointermediates. Three activation modes are established, and the important role of counterion via hydrogen bonding in determining the experimentally observed chemoselectivity is well rationalized by our calculations.
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