American Chemical Society
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Aromaticity-Driven Access to Cycloalkyl-Fused Naphthalenes

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journal contribution
posted on 2021-05-03, 13:05 authored by Karekar Sanjeev, Silver Raju, Srivari Chandrasekhar
We report the efficient synthesis of cycloalkyl-fused naphthalenes through the [4 + 2]-cycloaddtion/decarboxylative aromatization of alkyne-tethered aryne insertion adducts. These scaffolds were difficult to synthesize using conventional reactions. The reaction proceeds via the formation of a benzopyrylium intermediate followed by intramolecular [4 + 2] cycloaddition and a subsequent decarboxylation pathway. This method is also compatible with allene-tethered substrates to afford similar products. In addition, the one-pot synthesis of polysubstituted naphthalenes via aryne insertion/benzannulation has also been developed in good yield.