Synlett 2011(6): 741-744  
DOI: 10.1055/s-0030-1259712
SYNPACTS
© Georg Thieme Verlag Stuttgart ˙ New York

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

Tsun-Cheng Wu, Yao-Ting Wu*
Department of Chemistry, National Cheng Kung University, No. 1 Ta-Hsueh Rd., 70101 Tainan, Taiwan, ROC
Fax: +886(6)2740552; e-Mail: ytwuchem@mail.ncku.edu.tw;
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Publikationsverlauf

Received 8 November 2010
Publikationsdatum:
08. März 2011 (online)

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.

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The structure of 13 has been confirmed by X-ray structural analysis (Wu, T.-C.; Wu, Y.-T. unpublished results).