Modular Assembly of Spirocarbocyclic Scaffolds through Pd-0-Catalyzed Intermolecular Dearomatizing 2+2+1 Annulation of Bromonaphthols with Aryl Iodides and Alkynes

摘要

A novel palladium(0)-catalyzed dearomatizing 2+2+1 spiroannulation of 1-bromo-2-naphthols with aryl iodides and alkynes was developed for the rapid assembly of spiroindene-1,1'-naphthalen-2'-ones. This three-component cascade reaction was realized through consecutive Catellani-type C-H activation, unsymmetrical biaryl coupling, alkyne migratory insertion, and arene dearomatization. The potential utility of our method is illustrated by the one-step construction of the polycyclic skeletons of dalesconolsA and B from alkyne-tethered aryl iodides and 1-bromo-2-naphthol.