Pd-Catalyzed Intramolecular Dearomative [4 + 2] Cycloaddition of Naphthalenes with Arylalkynes
Jin‐Bo Lu, Xiao-Qiu Xu, Zi-Sheng Ruan, Kai Liu, Ren‐Xiao Liang, Yi‐Xia Jia
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.
Topics & Concepts
Intramolecular forceStereocenterChemistryCycloadditionElectrophileCatalysisVicinalCombinatorial chemistryMedicinal chemistryOrganic chemistryEnantioselective synthesisCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms