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

Chihiro Maeda, Hiroshi Shinokubo, Atsuhiro Osuka

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Pd-catalyzed annulation reaction of meso-hexynyl Zn(II) porphyrin with 4-amlno-3-lodopyrldlne 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 molety 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.

Original languageEnglish
Pages (from-to)2493-2496
Number of pages4
JournalOrganic Letters
Volume9
Issue number13
DOIs
Publication statusPublished - Jun 21 2007
Externally publishedYes

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Porphyrins
porphyrins
synthesis
Dimers
pyridines
dimers
palladium-meso-tetra(4-carboxyphenyl)porphine
products

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation. / Maeda, Chihiro; Shinokubo, Hiroshi; Osuka, Atsuhiro.

In: Organic Letters, Vol. 9, No. 13, 21.06.2007, p. 2493-2496.

Research output: Contribution to journalArticle

Maeda, Chihiro ; Shinokubo, Hiroshi ; Osuka, Atsuhiro. / Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation. In: Organic Letters. 2007 ; Vol. 9, No. 13. pp. 2493-2496.
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