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Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation. 2007

Chihiro Maeda, and Hiroshi Shinokubo, and Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.

Pd-catalyzed annulation reaction of meso-hexynyl Zn(II) porphyrin with 4-amino-3-iodopyridine efficiently provides meso-3-(5-azaindolyl)-substituted Zn(II) porphyrin as a major product, which assembles to form a slipped cofacial dimer by the complementary coordination of the pyridine moiety to the Zn(II) center. 2-iodoaniline and 2-iodophenol also undergo this [3 + 2] annulation with the meso-hexynyl Zn(II) porphyrin to furnish meso-indolyl- and benzofuranyl-substituted Zn(II) porphyrins, respectively.

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