Gold(I)‐Catalyzed Bis‐Cyclization of Allenynes for the Synthesis of Strained and Planar Polycyclic Compounds
Hitomi Tsuno, Jingfeng Shen, Hiroki Komatsu, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
Abstract
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.
Topics & Concepts
AlkyneAlleneChemistryPhenanthreneCatalysisNaphthaleneArylNucleophileCombinatorial chemistryCascade reactionFriedel–Crafts reactionNucleophilic additionRing (chemistry)PhotochemistryOrganic chemistryAlkylCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsSynthetic Organic Chemistry Methods