Gold‐Catalyzed One‐Pot Cycloisomerization/Nucleophilic Addition/Rearrangement of Acenaphthylene Carbaldehyde Derivatives

Merging the latest advances in field of gold catalysis and efficiency hexafluoro-2-propanol (HFIP), a gold-catalyzed orthogonal tandem reaction has been developed to access carbocyclic ketone on naphthalene substrates. The methodology involved cycloisomerization/nucleophilic addition C→O rearrangement. HFIP solvent most probably acted as Lewis-acid isochromene derivatives, through hydrogen donor bond activity. A large range acenaphthylene carbaldehyde engaged this process coupling behavior leading cyclic ketones with yield ranging from 15 91% (27 compounds). mechanism was investigated, presumably occurred via classical cyclization followed by [Au]-HFIP interaction for final interest such transformation demonstrated performing it gram-scale. Moreover, post-functionalization bromination performed, well isomerization some functionalized full trans derivatives 78 90% yields.