A gold-catalyzed cascade cyclization of naphthalene-tethered allenynes gave strained fused phenanthrene derivatives. The reaction proceeds through the nucleophilic reaction of an alkyne with the activated allene to generate a vinyl cation intermediate, followed by arylation with a tethered naphthalene ring to form the 4H-cyclopenta[def]phenanthrene (CPP) scaffold. When using aryl-substituted substrates on the alkyne terminus, the gold-catalyzed reaction produced dibenzofluorene derivatives along with the CPP derivatives. Selective formation of CPP and dibenzofluorene derivatives depending on the reaction conditions is also presented.
Keywords: Allenes; CPP; Domino Reaction; Gold Catalysis; Polycycles; Vinyl Cation.
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