Gold(I)‐Catalyzed Bis‐Cyclization of Allenynes for the Synthesis of Strained and Planar Polycyclic Compounds

Abstract

AbstractA 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.