Pd-Catalyzed Intramolecular Dearomative [4 + 2] Cycloaddition of Naphthalenes with Arylalkynes

Abstract

A Pd-catalyzed intramolecular dearomative [4 + 2] cycloaddition reaction of naphthalenes with arylalkynes is developed. The protocol provides a straightforward method to access a range of polycyclic dihydronaphthalenes containing two vicinal all-carbon stereocenters in moderate yields under mild conditions in an air atmosphere. The deuterium labeling experiment suggests a pathway involving electrophilic dearomatization followed by Friedel–Crafts cyclization. Several synthetic transformations of the product were conducted to demonstrate the utility of this reaction.