Carbocycle Synthesis Through Palladium-Catalyzed Dearomatization Of Naphthalene And Phenanthrene Allyl Chlorides

Dearomatization reactions of arenes have attracted considerable attention because they provide a simple way to synthesize functionalized alicyclic compounds, which can be used as intermediates for the preparation of natural products and bioactive compounds. Over the past four decades, many methods, including oxidation, reduction, photocycloaddition, [2,3]δ-rearrangement, electrophilic addition, nucleophilic addition, and other approaches have been developed for breaking up the conjugatedπ-system. In 2001, Bao et al reported the facile palladium-catalyzed allylative de-aromatization reaction of benzylic chlorides with allyltributyltin. Contrast to other dearomatization reactions, this kind of dearomatization reaction could proceed smoothly at room temperature, and the dearomatization products could be easily isolated without arrangement.In this thesis, palladium-catalyzed allylative dearomatization reactions of naphthalenes and phenanthrenes bearing 3-chloroallyl moieties were described. The allylative dearomatization reactions of naphthalene and phenanthrene allyl chlorides with allyltributylstannane in the presence of palladium catalyst proceeded smoothly to provide dearomatization products in high yields (74-89%). The dearomatization products were very stable, and which can be used as building blocks in organic synthesis for construction of new organic compounds. The identities of dearomatization products were established by NMR andIR spectroscopies as well as HRMS determination.