Metal-Catalyzed Cascade Reactions of Ethynyl-Substituted Naphthalenes: Synthesis of Polycyclic Arenes

Abstract

Palladium-catalyzed cycloaddition reactions of 1,8-diethynylnaphthalene derivatives with o-diiodoarenes take place to generate the corresponding benzo[k]fluoranthene-based linear acenes in moderate to good yields. In addition, 1-ethynyl-8-iodo­naphthalenes undergo palladium-catalyzed cyclodimerizations to produce zethrenes. Finally, in the presence of a catalytic system comprised of [NiBr₂(dppe)/Zn], 1-ethynyl-8-iodonaphthalenes reacts with nitriles and 2-butyne to form the respective pyrroloarenes and pyrene.

arenes - cross-coupling - cycloadditon - nickel - palladium - polycycles

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12

The structure of 13 has been confirmed by X-ray structural analysis (Wu, T.-C.; Wu, Y.-T. unpublished results).