Palladium(II)-Catalyzed Oxidative Dearomatization of Free Naphthols with Two Alkyne Units
Organic Letters2014Vol. 16(23), pp. 6132–6135
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Abstract
Readily available 2-naphthols undergo [2 + 2 + 1] spiroannulation reactions with alkynes in the presence of a Pd(II) catalyst and an oxidant. This process relies on C-H functionalization and naphthyl ring dearomatization at the 1-position of 2-naphthols to provide a variety of spirocyclic compounds. Using alkyl-aryl alkynes as the coupling partners led to regioisomeric mixtures in favor of the head-to-tail isomer bearing a quaternary carbon stereocenter.